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How to Wear Cowboy Boots


Red Cowboy Boots
Photo by The Department

Here’s another article that was inspired by a reader question:

I’m subscribed to CF and read all the posts. I just purchased the cutest brown cowboy boots, but am finding it hard to find outfits to wear them with. Please help, How do I wear cowboy boots?” – Abby

I personally like the look of cowboy boots, and even though some hardcore Vogue readers will claim that they aren’t “in” right this second, I am a believer in wearing what you like, just making sure to wear it the right way! There’s no fashion discrimination here, except maybe against pajamas in public

Read on to learn how to wear your cowboy boots while avoiding looking like you’re trying out for a part in the next Dukes of Hazzard… It’s not hard, I promise!

Cowboy Boots With Jeans

This is probably the most classic way to wear a pair of cowboy boots. There are two ways to do this, and which one you pick depends on your personal style and which type of jeans you prefer!

Under Your Jeans

Jeans Over Cowboy Boots

Your boots will look like high heels, giving you a bit of height while still keeping your outfit casual. This look works the best with flared or wide-leg jeans, because cowboy boots are usually pretty wide around the leg, and could look bulky if you wear a more tapered jean. Also, make sure your jeans are long, because the goal isn’t to show off too much of the boot in this case.

This look is great because the toe of the boots peeking out from under your jeans will make your legs look super-long and thin, always a plus!

Over Your Jeans

Jessica Simpson and Sienna Miller wearing cowboy boots tucked into jeans

Cowboy boots are perfect with the skinny jeans of last season if they’re still in your closet – it’s so easy to tuck skinny jeans in to any boot. If you don’t have any skinny jeans, regular straight legs can be folded over and tucked in to show off the boots. Try pairing this look with a leather jacket and structured bag to tone down the country-ness.

Cowboy Boots With A Dress

I love this look personally, even though it might not be the most “right now” way to wear it. This style has gotten a lot of flack recently because apparently Britney Spears loves to wear her cowboy boots with short dresses around LA. Don’t let Brit deter you though – it’s actually a super-cute way to wear cowboy boots if you pick the right dress and accessories.

With An Airy, Flowery Dress

Ashley Olsen, Miley Cyrus and Jessica Alba wearing cowboy boots with dresses

One popular way to wear cowboy boots is with a flowery, loose and/or casual dress, as seen in the looks above. Go simple and white like Ashley Olsen or Jessica Alba, or for a more extreme look, pair boots with a colorful dress like Miley. (Disclaimer: Miley’s outfit is for the fashion-adventurous only!) Also, your dress should be above the knee, but not too short!

For some dress ideas, try Jovovich-Hawk for Target. I think their dresses would go perfectly with cowboy boots! Also, check out my article on Boho Chic for more dress ideas that work with cowboy boots.

With A Classic & Simple Dress

Rachel Bilson and Taylor Swift Wearing Cowboy Boots

This way of wearing cowboy boots is my favorite of all! Rachel Bilson pulled this look off perfectly this past fall, when she wore bright red cowboy boots with a simple black dress. I love her look! Although Taylor Swift’s outfit was controversial in the fashion community when she wore the ensemble above (some loved it and some hated it), I think it was cute and showed her personality without being overly “country.” Both ways were cute and casual but still elegant.

To get this look, just wear your cowboy boots with a simple and understated dress. Keep the rest of your look simple: don’t wear too much other stuff or else you’ll risk looking too overdone.

Cowboy Boots With Leggings or Tights

Wearing cowboy boots with leggings or tights is a little bit more daring than the jeans or just a dress looks, but I think it can work really fabulously if you do it right and have the confidence to pull it off!

I like the look of brightly colored tights or leggings under a plain pair of cowboy boots, paired with a simple dress and possibly a cardigan if it’s a little cold out.

With Leggings

Mary Kate Olsen wearing cowboy boots and leggings

The above photo of Mary Kate Olsen circa 2005 was the best picture I could find of someone rocking cowboy boots with leggings. It’s one example of a way to wear cowboy boots with different types of legwear. An extension of this look that might work would be non-ripped leggings, cowboy boots and a tunic dress and cardigan. Remember to keep the colors in your outfit simple because the cowboy boots are a statement in and of themselves.

With Tights

Wardroberemix girl

I found the above photo of Flickr user iluvrhinestones on Wardrobe Remix and thought it was a great example of a stylish and unique way to wear cowboy boots. Tights look cute with boots and you can wear them with dresses for a cute spring outfit that doesn’t require bare legs! Take a cue from the photo above and try wearing your cowboy boots with a dress or tunic and bright tights.

How Not To Wear Cowboy Boots

Here are a few examples of what NOT to wear with your cowboy boots.

Don’t go “cowboy themed.” You aren’t trying to wear a costume, you’re trying to incorporate a pair of shoes into an outfit. Leave the checkered tops, fringe and super short Daisy Dukes for other outfits to avoid looking cliche and over-the-top.

Don’t wear them with a loud outfit. Keep the rest of your look simple if you’re going to wear cowboy boots. They make a statement on their own, so let them be the focus!

Don’t wear them every day! Cowboy boots are better as a once-in-a-while thing. While you may love them like crazy, switch off with your other footwear to avoid being branded “that girl with the cowboy boots.”

These are just some of my ideas on how to wear cowboy boots. Feel free to improvise with your own and be creative in your outfit choices!

What do you think? Do you like cowboy boots or do you think they’re so five years ago? If you like them, how would you wear them?

Posted on on April 14, 2008 / Filed Under: Fashion Tips / Tags: , , ,

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158 Responses to “How to Wear Cowboy Boots”

  1. 1
    April 14th, 2008 at 7:21 pm

    I think Cowboy Boots are adorable. I go to Texas A&M University in College Station and am surrounded by “Farmers in Boots” and I love it! I don’t think boots will ever go out of style. My mom gave me an old pair that she used to wear and those are the ones that I get the most compliments on! So fun!

  2. 2
    April 14th, 2008 at 9:28 pm

    Thanks for these tips I’ve been wanting to get a pair of Frye boots but I had no idea how I would wear them, now I have some ideas. Keep up the great website :)

  3. 3
    April 15th, 2008 at 2:20 pm

    I have a pair of skinny cowboy boots I stole from a friend…and they are the most glorious pair of shoes I own. I only wear them every few months, but I pair them up with minidresses and skirts — shows the boots off quite well.

  4. 4
    April 15th, 2008 at 4:21 pm

    oh thank you for this post! I have a pair of cowboy boots from a few years ago that are the real deal. i lvoe them to death and will wear them regardless of if they’re “in” !:)

  5. 5
    April 20th, 2008 at 5:51 pm

    Ashley – I’m sure in Texas the cowboy boot will definitely be popular forever! Whenever I think cowboy boots, I definitely think Texas. And that’s awesome that you have vintage ones – they’re the best!

    Alyssa – No problem, anytime! And thank you! :)

    Alex – The cowboy boots with minidresses & skirts look is one of my favorites! I’m glad that it’s finally getting warm enough out to wear it too!

    Lauren – You’re welcome! Also, that’s the way to do it with fashion I think – wear what you want and don’t worry so much about what’s in!

  6. 6
    April 21st, 2008 at 11:15 am

    it’s unbelievable! Today I was doing some rearranging around the closet (I’m talking like it would be the size of a football field :)) ) and I came across my cowboy boots faux suede, lila, completely adorable that I loved so much and keep against all odds for almost 3 years now. I asked myself – wow, if these things could still go on, I would be soooo happy! Wonder if they would.. Well, I have my answer now, reading your article and respecting some good sense, nothing is really out of fashion!

  7. 7
    April 21st, 2008 at 11:18 pm

    Kpriss – Guess we’re psychic, haha :) And yes yes yes, I’m a total believer in wearing what you want and not being a slave to the trends. You have to have fun with it! I love following the trends sometimes, but I can take em or leave em, and that’s how I think it should be for everyone!

  8. 8
    April 23rd, 2008 at 8:07 pm

    do you know where to buy some reasonably priced ones?

  9. 9
    May 4th, 2008 at 1:30 am

    I like the idea of wearing them with a flowy dress, but can you wear this look/shoe for the spring?

  10. 10
    July 6th, 2008 at 11:54 am

    I just got my first pair of boots! I found a pair of Roxy ones on ebay. I LOVE them!! I was trying to figure out what to wear them with but now I have tons of ideas! Thanks!

    And like you said, it doesn’t matter if things are in or not. Wear what you want! It doesn’t matter what others think! :)

  11. 11
    September 20th, 2008 at 6:20 pm

    Cowboy Boots With Dresses is one of the ugliest fashion statements ever!

  12. 12
    October 3rd, 2008 at 3:22 pm

    I LOVE cowboy boots, i think they are sooo cute!
    And actually, i think cowboy boots with dresses, is the cutest way to wear them. (as opposed to what mr said)

    I want to buy some, cause i don’t own any.
    I spent like all summer trying to find the perfect pair, but sadly there weren’t many around that i liked. But lately i’ve been seeing A LOT of boots. I’m going shopping today, hopefully i find my perfect cowboy boots. And here in LA it’s still SUPER hot, so i can still wear them with summer dresses and stuff. =]

  13. 13
    October 17th, 2008 at 6:56 pm

    I found a gorgeous pair of Franco Sarto cowboy(girl) boots in a fantastic bronze brown color. Simple in design but fabulous. The best part of all, I found them in a Thrift Shop for $20.00. They are the real thing, trust me, I shop alot. in named brand stores. I wear an 8 1/2 and practically drooled over handcrafted western boots since my trip to Sante Fe, NM last summer, but no way could afford those custom boot prices. These just fell into my cart one day while shopping and were almost new. Someone was silly to get rid of these babies.

  14. 14
    November 1st, 2008 at 7:25 pm

    The cowboy boot trend is definitely back. It comes and goes often but when it goes it never stays gone for long, if you have em, keep em, they always come back. I’m about to search for a pair of cute brown ones right now! Wish me look.

    Jaime, – Your source for all things fashion

  15. 15
    November 3rd, 2008 at 2:08 pm

    I would love to sponsor this page. My website is
    please email if you are interested.


  16. 16
    December 6th, 2008 at 4:01 pm

    I would just like to say that I love the style with the cowboy boots and a dress….. in fact, I wore a dress and boots to a dance in middle school….. and this year I wore them with my dress to homecomming.
    I think that if you really like boots or are a real cowgirl then it is fine… even if you get made fun of, you know that the other girls aren’t brave enough to wear them. I also had somebody to dance with each slow song!

  17. 17
    December 8th, 2008 at 11:20 am

    I have a pair of really fancy looking Diesel cowboy boots. They are adorable but not plain boots like those recommendation above.. it has 4 colors, mainly dark blue & white contrast. I wear it with denim skirts so far. Please give me some other ideas how I can wear them. Thank you!

  18. 18
    December 18th, 2008 at 6:05 pm

    hey i know this isnt about ur “How to” but i was just wondering if u know where the first jeans in the first picture of jeans are from? im shopping for jeans and kinda wantt to buy them they are sooo cutee! id reallly like to knowww!! please and thankk youuu! :)

  19. 19
    January 10th, 2009 at 11:40 am

    Hey!! Thank you for all the ideas!!! If anyone is looking for a dress or boots, try
    the boots are expensive, but they’re super cute and there’s a pair at Shoe Carnival JUST like it for $100 less. And, if you look at the bottom, “You Might Like These, Too” there is an ah-dorable dress. It comes in like, 4 different colors!! Everything on that website is super cute and they have lots of skirts, tops, bags, and other stuff to pair with the boots…..
    happy hunting:)

  20. 20
    January 11th, 2009 at 5:02 pm

    Okay, sorry, the link didn’t work, but here are instructions to the site:

    2. go to “Shoes” and down to “Boots”
    3. they’re the first ones, so click on them
    4. you’ll see a big image of them, scroll down
    5. under “You Might Like These, Too” look for the “Juliet Eyelet Dress”

    and you’re done. to see the dress’s other colors, click on the dress:))

  21. 21
    January 15th, 2009 at 4:32 pm

    That was the same question I had, thanks! I am trying to find the “Airy, Flowery Dress” look from the first picture but am not having any luck. :( I am short (5’2″)and size small, does anyone know where I could find a dress like that?

  22. 22
    January 23rd, 2009 at 10:57 pm

    i just bought a pair of cowgirl boots. they are dressy and the heel is 2 and 1/2 inches. i am aiming for a more worn in, distressed look. how do i establish that with this new pair that came fresh out of the shoe box?

  23. 23
    January 26th, 2009 at 2:38 pm

    I just bought of pair of vintage cowboy boots at a vintage store. They are super adorable and worn just enough to show that they are indeed “vintage”. Theresa, you asked how to give yours that distressed look. Well, the owner of the vintage shop I visited told me a “secret” that was passed along to him from someone in Texas. Back in the day, he said, cowboys used to walk in a stream of water with their new boots on. He said that’s the secret to getting them to fit your feet perfectly. He also said that helps to give a distressed look. I was concerned about this (wouldn’t that ruin the leather?), but maybe if you rub a water protectant on the boot, that might help to deflect any water staining to the leather. Again, I’m not sure if this will even work, but it’s something he passed along to me. Who knows…

  24. 24
    January 26th, 2009 at 8:16 pm

    I love your Ideas I’m from texas and my dads old fashion and say s cowboy boots dont look good with dresses or with pants tucked in. this helped soften him up./ But I do do one of your donts I wear mine pretty much every day but that is cause I want to be branged that cowgirl. Thats me and I do have more than one pair of boots.

  25. 25
    February 5th, 2009 at 7:13 pm

    :D AWESOME! Only googled how to wear cowboy boots because I just bought a pair (mostly because I am going to go to a Brooks & Dunn concert and wanted to be comfy and taller so i figured a heeled cowboy boot would be a great idea, plus they are super cute) but now I’ve found a wicked awesome fashion website for people my age! SCORE! lol.

    Tonight going to the ever popular Irish Pub in the city and trying the floral girly dress and boots look. Kind of 80’s/90’s country rock film clip, but lookin cute as! :D

    I totally want a red pair not just a tan pair now!!! I have thing for red shoes…

  26. 26
    February 5th, 2009 at 10:50 pm

    I am glad I stopped by to read this post. It is refreshing to read an author who knows the subject matter. I will be adding you to my reader.

  27. 27
    February 14th, 2009 at 8:30 am

    amazing stuff thanx :)

  28. 28
    February 17th, 2009 at 5:31 pm

    hey. i recently wore my cowgirl boots to school and i wore them under my jeans with a white shirt. some people said stuff like “oh those shoes look better on so and so”, or “u should pull ur jeansover them.” It just tore me apart because i was so excited about wearing them and i loved them so much but now i really dont wanna wear them anymore because of what people said. what should i do? please help.

  29. 29
    February 17th, 2009 at 6:00 pm

    Taylor – Don’t listen to what anyone has to say about your clothes! To be honest, they’re probably just jealous of you. And at the end of the day, if you like your outfit, that’s all that matters. It’s not up to them to decide what you should wear! Be fabulous and don’t worry about what haters think. I’m sure you looked great :)

  30. 30
    February 25th, 2009 at 8:23 pm

    How old is too old to wear cowboy boots with a dress??

  31. 31
    March 6th, 2009 at 7:24 pm

    Nice. Banger > Taylor Swift + Mom Jeans

  32. 32
    March 7th, 2009 at 3:45 pm

    Love it!
    I just got new cowboy boots and not only will they be practical to ride my horse, I will also be able to wear them with style!

  33. 33
    April 14th, 2009 at 12:07 am

    I’ve seen Taylor Swift wear these really cute brown cow boy boots, but I can’t even find any like them. They had like a cute design on them, but I’m sure they may have been custom made. I was wondering where I could find some really nice cow boy boots that look authentic and not cheaply made. Thanks!

  34. 34
    May 3rd, 2009 at 6:07 pm

    Cowboy boots are comfortable, stylish, and can go with almost anything. My favorite is wearing them with sundresses or denim shorts and a cute dressy tank top and jewlery, its absolutely adorable. dont ever be afraid to where them, they are cute and make you look brave and bold.

  35. 35
    June 2nd, 2009 at 9:46 pm

    You can find really nice cowboy boots at Cavenders or Sheplers. I’ve found some that I like by Ariat that are really cute and are about $140 some might think that’s alot for cowboy boots but it will be worth it in the end because cowboy boots are always going to be in style. I hope I helped you some.

    I agree with you and I love the whole sundress and cowboy boots together!

  36. 36
    June 2nd, 2009 at 9:49 pm

    Lots of girls in their 20’s are wearing sundresses with cowboy boots. I’ve seen older ladies around 40-50 wearing it so I guess you can’t be too old to wear a dress with cowboy boots.

  37. 37
    June 10th, 2009 at 4:01 pm

    I loved this article! Where can I get a pair of cowboy boots that Taylor Swift would wear. They need to be about $100 (a little more/less) and I would like them to be brown….and like calf high. I want them to be cowhide. HELP!

  38. 38
    June 10th, 2009 at 4:02 pm

    I like the ones in the picture above, if they were brown. Where are those from?

  39. 39
    June 12th, 2009 at 4:58 pm

    i have also been on a search for really cute cow boy boots and i was looking at different websites, and hear are a few that i think might help you out:

    HELP please!
    I’m saving up for a pair of really cute cow boy boots…I love the way that they look and it would be easy for me to wear them everyday. How often is too often to wear them?

  40. 40
    July 14th, 2009 at 10:13 am

    i absulotely adore cowboy boots; i have a flat pair and pair with heels.
    personally, i prefer the heels, as i’m only a mere 5ft, so they add height, without being terribly obvious.
    i LOVE cowboys with bootcut jeans/dresses.


  41. 41
    July 24th, 2009 at 6:04 am

    Jusy got my 1st pair of cowboy boots today :D Gonna break them in this weekend – sooooooo excited! Thanks for al the great ideas on outfits, defo agree on demim shorts/skirts & flowly sundreses – cheers!
    Check them out:

  42. 42
    September 12th, 2009 at 10:42 am

    Thank you so much for providing this info!!
    I was just going to purchase a pair of really expensive ones and I wanted to make sure I could wear them to places other than a rodeo and still look cute:)
    The pics are awesome and the don’ts are really helpful, I can definitly rule out wearing a plaid top with them!

    Thanks again

  43. 43
    September 20th, 2009 at 4:11 pm

    I think the boots these days that are available for women are awesome. I personally prefer them with jeans, but their popularity is growing so that you can wear them with almost anything. Thanks for the post. Learned a little more about wearing cowboy boots for women.

  44. 44
    October 5th, 2009 at 4:37 pm

    I love this artical. Totally helped me. I love cowboy boots. Which is kind of hard to pull them off in Connecticut,being cowboy boots are usually frowned upon here. :/ Whereas,when I went to Texas in 07, (My Dad lived there) – EVERYONE was wearing them. Felt right at home. ^.^

    Anywhoo.. Last year in 8th grade. Like the only outfit I wore was bootcut jeans,black cowboy boots,a blue and black button up and a black rodeo belt. – Weird I know. And no one really commented on them. Which,hey – If they don’t have anything nice to say,then don’t say anything at all.

    Over the summer…. I went to Tennessee and picked up a cute pair of slouchy brown Dingo boots.

    Tomorrow I plan to wear them. I plan to wear them with skinny jeans,a tan top and a brown tanktop underneith,since the top is abit sheer. I think I could pull it off,being I’m now in High School and you can usually pull ANYTHING off there.

    Just deciding on which shade jean to wear.. Light denim or dark denim.. :/

  45. 45
    October 6th, 2009 at 4:18 pm

    Im very small in height and have a small foot for a adult and I have looked everywhere for a fashionable cowboy boot that has some cool design on it and tan colored. I wear a size 3 in girls and a 5 in ladies. Can anyone help as far as what would be a good website to buy some from?

  46. 46
    October 7th, 2009 at 7:22 pm

    hey i love them tooo but this is gay

  47. 47
    October 9th, 2009 at 10:53 pm

    I have a problem with my cowboy boots!! :(
    I recently got a black jus above the ankle cowboy boot and i wore them with these skinny jeans, and a a lil fitted tunic. The problem is my ankles are really skinny that my boots looked like they were a size too big! They obviously arent but i dunno how im gonna wear them because they were also final sale!! i feel like i have totally wasted $80!! :(

  48. 48
    October 27th, 2009 at 8:04 pm

    Heyy so I live in Houston and love love love boots and country music. I have a pair of Ariat boots that i got from Cavenders and i love wearing them with my jeans and this cute sundress that i got from Target with a braided belt. I think boots will always be in style and you should wear whatever you want. And taylor swift wears dresses with boots so mr stop criticizing dresses with boots b/c i think they are a great combination.

  49. 49
    November 6th, 2009 at 9:54 pm

    Hi! great website just what i was looking for. Thank you x

  50. 50
    November 19th, 2009 at 9:56 pm

    Love the article. I love cowboy boots and haven’t seen this kind of info online. Great job. I got a pair of these Old Gringo boots and wore them to fanfare last year. I got so many complements on them.

    Check them out-

  51. 51
    November 24th, 2009 at 1:37 pm

    I think cowboy/cowgirl boots look hella awesome espieclly if their black boots paired with grey skinny jeans, white shirt, black leather jacket.
    i just bought some black cowboy boots and they have a inch heel,. they’re cute, but i don’t have the jacket yet to wear and that’s driving me crazy because that completes the outfit.

  52. 52
    November 27th, 2009 at 6:40 am

    oh my god thnks for the article,,,by the way here in phils its not that popular to wear cowboy outfit coz its not in.

  53. 53
    November 28th, 2009 at 1:47 pm

    I just bought my first pair of cowboy boots yesterday at KMART! i saw a pair in a store for $150 but i bought them yesterday for $30! They look exactly like those other expensive ones. I wanted to wear the boots today but didnt know what to wear them with but now I know! Thankyou!

  54. 54
    December 4th, 2009 at 10:24 am

    I’m so happy the cowboy boots trend is so popular. And your article is so helpful….especially the don’t. Just a few simple rules, and anyone can look amazing in cowgirl boots!

  55. 55
    December 7th, 2009 at 9:17 pm

    I got a pair of Dolce Gabbana cowboy boots for $1,500 and i have’nt worn them since but now i have decided to wear them and this article has helped me alot!

  56. 56
    January 4th, 2010 at 2:04 pm

    i bought this cute pair of short grey cowboy boots (miz mooz, cozmuel, Nordstroms) and i love them but i too have a hard time finding ways to wear them. I do wear them with flared jeans and it gives them a cute edge- instead of wearing tennis shoes. i think tucking in jeans and wearing a simple shirt looks casual but great.

  57. 57
    January 5th, 2010 at 10:36 pm

    Jessica Simpson has some really cute cowgirl boots on her website!!!

  58. 58
    January 21st, 2010 at 1:34 pm

    Happend on your site while looking for my THIRTEENTH pair of cowgirl boots. Yeah, I know – I’m obsessed. You young people are so cute. QUIT worrying about who thinks what on your clothes/shoes/boots. Wear whatever the hay you want to and be proud of it. I’m 75, and wear boots EVERY DAY – don’t wear shoes anymore, but when I did, I had 122 pairs. I still go country dancing, and of course, wear my boots. Have them in several colors, but can’t find green ones. I wear them under jeans around town and w/broomstick skirts for dress up and dancing. Also wear western belts and hats to coordinate. Favorite store and website is Sheplers. They have a wonderful selection, and their service is excellent. I live in and love Texas!!!!!

  59. 59
    January 21st, 2010 at 2:55 pm

    So.. Reading through this artical I read about not wearing plaid with it..

    Have a question… Would this be.. “Socially” Acceptable..?

    Boots: (black)

    Shirt: (Mine is black & red)


    and then under the plaid shirt I will have a black fitted cami with a lace vneck. The plaid shirt being open.

    Keep in mind this is in Tennessee…..

  60. 60
    February 16th, 2010 at 4:53 pm

    I think you took some of your pictures for this blog from my website without giving me proper credit.

  61. 61
    February 16th, 2010 at 5:04 pm


    That w/be a darlin’ combination to wear. I have those boots. Wish I had the shirt. I received a new denim skirt today from Soft Surroundings. Wearing it w/brown boots and a beige/off-white cowhide belt tonight to the Perot Theatre. Here’s their website:

  62. 62
    March 11th, 2010 at 6:44 pm

    I LOVE my cowboy boots, it’s all I ever wear but thats the kinda girl I am. I own about 4 pairs, the places I’ve had the best luck at finding boots is Boot Barn & Tractor Supply. My 2 favorite places!!!

  63. 63
    March 12th, 2010 at 7:58 pm

    I absolutely adore cowgirl boots!, Their is this cowboy im after and i want to impress him with my cowgirl looks, I cant wait to get the cutest pair ever! keep adding pictures of them!! Byee!! :)

  64. 64
    March 15th, 2010 at 8:20 am

    Firstly thanks for tips. This is a lovely tip where everyone would love to know and clarify their droughts and the cowboy boots suits on jeans as well as on the flowery dress or classic dress. I have a lovely boots with brown and a black outsole which looks amazing and elegant in all the dresses. The pink cowboy boots looks cute and lovely.

  65. 65
    March 18th, 2010 at 10:44 am

    i still dont understand what colors to wear with tan and brown cowboy boots i really nedd some help

  66. 66
    April 5th, 2010 at 11:46 am

    Is wearing a denim vest with cowboy boots and a dress too much country? Cause I have the outfit and it looks adorable, but I’m just curious as to whether that is just too much.

  67. 67
    April 13th, 2010 at 10:50 am

    I have a pair of cowboy”ish” boots they look like theses

    But the thing is whenever I try to find something to wear them with I think I look really really stupid, I need help to find out what to wear with these boots because they cost me alot of money and I really love these shoes!!

    Thanks, ShopTilWeDrop

  68. 68
    April 19th, 2010 at 11:56 pm

    There is noting wrong with being branded as girl with the boots. If that’s how you are then be yourself. If you like them wear them as you like. It sure isn’t a don’t. There’s also nothing wring with being country. So it’s also not a don’t : )
    express yourself how you want to.

  69. 69
    April 20th, 2010 at 10:15 pm

    If you are looking for a fashion forward cowboy boot try Old Gringo Boots. I have started styling the stars in these unique style of cowboy boots. If you want the perfect boot for your personality I can find it. Email me for a personal boot experience, there is a style for everyone, and everyone should have a pair of cowboy boots in the closet.

  70. 70
    April 29th, 2010 at 8:42 pm

    Love the Pink boots!!
    To sweet!!

  71. 71
    May 19th, 2010 at 10:30 pm

    Plenty of girls rockin’ the boots with leggings and dresses in Texas!

  72. 72
    May 26th, 2010 at 11:52 am

    I live in alabama- born and raised! a lot of people wear boots, all the time but mostly to work it and what not however, i got a reallllyyyy cuute pair of cowgirl boots and i love the way they look with dresses but my mom thinks that they look stupid and she wont let me wear them with a dress Im trying to convince her its stylish!! can you help in any way ???

  73. 73
    June 2nd, 2010 at 4:12 pm

    I go to Texas A&M University and I fell in love with cowboy boots. I have my eye on a pair and I was looking online for outfits I can wear with them. This post helped a lot! Now I’m obsessed with the blog.

  74. 74
    June 24th, 2010 at 9:03 pm

    LADIES LOOK G R E A T in Cowboy Boots!!!! And a Man can never have enough boots. Now girls, start checking out eBay for really fine true cowboy boots. Run a Search like “cowboy boots”, then REDEFINE it in the left hand options column for “ladies”; sizes “6, 6.5, 7, 7.5″, etc. Used boots are GREAT finds. They’ve usually been broken in, can be of the highest quality, some absolutely unique not to be seen again styles, and absolutely dirt cheap for what you get. BUT sizing is most important. You ARE going to have to know your size in at least one of the major brands like JUSTIN, TONY LAMA, or NOCONA. If any readers are interested, just post here and I’ll try to answer any questions to help you enjoy one of my favorite pastimes.

  75. 75
    June 28th, 2010 at 1:20 pm

    Thanks for the lovely tips. I wear cowboy boots with jeans and a long cardigan or tunic and such look can look good anywhere.

  76. 76
    July 11th, 2010 at 10:11 pm

    I don’t think there is anything wong with wearing cowboy boots everyday. there ain’t nothing wrong with wearing them with super short daisy dukes either . personally I think there adorable . im pretty rednek and wear mine all the time and with daisy dukes alot to. they’re really comfortable and great to wear when you go to a mud bogg too.

  77. 77
    September 20th, 2010 at 3:17 pm

    wearing boots to gameday (college football) is a must in the south.

  78. 78
    October 29th, 2010 at 10:24 pm

    Maybe you could change the blog title How to Wear Cowboy Boots – College Fashion to something more generic for your subject you make. I loved the blog post all the same.

  79. 79
    November 7th, 2010 at 3:31 pm

    I love cowboy boots. I go to school in the south and I wear mine all the time. Certainly nothing wrong with that, because lots of other girls do too. Cowboy boots are timeless and I’m sure they will always be! :)

  80. 80
    December 26th, 2010 at 12:13 pm

    I just bought a pair of pink cowgirl boots from Texas and I ware them with jeggings and summer dresses!

  81. 81
    January 1st, 2011 at 9:02 pm

    I just bought my first pair of cowboy boots and i am in love with them!! I got them from Payless Shoe Source for $40!! Cant wait for the summer so i can wear them with some dresses!

  82. 82
    January 2nd, 2011 at 9:23 am

    Geesh Elizabeth, why can’t you wear them now w/jeans? I wear mine year round w/jeans and long skirts. I gave three pair to my daughter, and just bought my 12th pair. I know – I’m sorta addicted to boots.

  83. 83
    January 2nd, 2011 at 8:48 pm

    haha..i didnt mean that i was only going to wear them in the summer, i meant that i really want to wear them with dresses also!

  84. 84
    January 16th, 2011 at 2:04 pm

    Thanks for these awesome ways to wear cowboy boots!

  85. 85
    February 2nd, 2011 at 6:39 pm

    Personally, I wear cowboy boots for one reason-to ride horses and rodeo in. That’s technically what they were made for, the heel of the boot keeps your foot from sliding out of the saddle’s stirrups. I think it’s funny how everyone just started wearing them a couple years ago lol. Now all my friends that don’t ride are wearing them. But, whatever floats your boat I guess. I wear them 24/7, but I’m not worried about being labeled ‘the girl in the cowboy boots’ cause I’ve already been labeled ‘cowgirl’ for riding horses all the time haha. Also, I wear them with jeans tucked in, over my jeans, and dresses. Also, very unfashionably, I wear them with basketball shorts, sweatpants, or whatever lol. Doesn’t matter to me, as long as I’m riding my horse (:. Daisy dukes, flannel and plaid shirts, and fringed chaps are common as well :D. See ya’ll.

  86. 86
    February 2nd, 2011 at 9:41 pm

    I really dont like this trend!! Its probably because I live on the east coast but I’m really not feeling it.

  87. 87
    February 7th, 2011 at 10:15 pm

    I need to find a jacket like Jessica Simpson is wearing in the picture above!! Goin to a Miranda Lambert concert next weekend and im thinking itd be perfect with my black and gold corral boots!! Please someone help me find one! THANKS

  88. 88
    February 20th, 2011 at 10:51 pm

    I love cowboy boots. they are so comfy. i wear mine all the time. i think ive already been labeled ‘the girl with the cowboy boots’ so i aint worried about that. like TP said, i also wear mine over jeans, under jeans, with sweat pants, and basketball shorts. and to ride in. i dont like dresses and skirts so i dont wear those haha. but yeah. i mostly like em with sweat pants because they are both comfy so my day can go easier and more comfortably. :] k. thanks.

  89. 89
    February 23rd, 2011 at 8:02 pm

    Hey! Does anyone know a good website to buy some?

    I had my eye on a pair at wet seal, but they don’t have my size left.

    Any ideas?


  90. 90
    March 2nd, 2011 at 7:22 am

    Where I’m from, myself and one other guy wear cowboy boots. I’m a southern girl at heart and will be moving to Texas this summer so I was down there 2 months ago and finally bought these awesome boots :) if you have any tips on breaking them in…my feet would love you for that!

  91. 91
    March 21st, 2011 at 3:38 pm

    I wear my boots everyday, that’s how the girls in Iowa do it! We don’t need a blog to tell us how to wear our boots. Always && Forever–A Tony Llama Girl!

  92. 92
    April 13th, 2011 at 3:18 am

    Cowboy boots are probably the most fashionable in the winter.

    I haven’t really seen anyone wear cowboys boots in the summer.

    Maybe only in texas? lol

  93. 93
    April 19th, 2011 at 10:37 pm

    I wear my cowboy boots year round. I practically live in them. So comfortable and because I live in the Pacific Northwest, you don’t see them around that often, so I get complimented on them all the time. And I’ve yet to be branded the “girl in the cowboy boots”. :)

  94. 94
    April 25th, 2011 at 10:55 pm

    I absolutely love my cowgirl boots. i own two pair of nice donald pliner western boots and they are great with jeans. as a matter of fact, i am going to rock a pair of brown and biege ones with some nice cut-up jeans to a comedy concert on sunday. i live in the midwest and the weater has been a cooler this spring, so i want to be cute; yet comfortable.

  95. 95
    April 25th, 2011 at 10:56 pm

    I absolutely love my cowgirl boots. i own two pair of nice donald pliner western boots and they are great with jeans. as a matter of fact, i am going to rock a pair of brown and biege ones with some nice cut-up jeans to a comedy concert on sunday. i live in the midwest and the weather has been a cooler this spring, so i want to be cute; yet comfortable.

  96. 96
    May 17th, 2011 at 3:44 pm

    Western boots are a great way to update your wardrobe since they don’t seem to ever go out of style!

  97. 97
    May 25th, 2011 at 9:18 pm

    I’m a Texas gal, and one of the best places to find affordable boots is Cavender’s Boot City. Check it out online!

  98. 98
    May 26th, 2011 at 11:50 am

    so the question i was looking for the answer to never got answered ….How old is too old to wear this style???

  99. 99
    May 26th, 2011 at 3:51 pm

    I’m 76, wear them exclusively, and plan to be buried in them. Donna – don’t let others dictate to you what , when, where, how to wear your boots. Dress to suit yourself.

  100. 100
    June 11th, 2011 at 8:31 pm

    Can I wear denim shorts with brown distressed cowboy boots or will I look silly?

  101. 101
    June 21st, 2011 at 12:05 pm

    i usually wear my cowboy boots with buckle shorts but i dont do the whole cowboy outfit and i think the outfit is really cute! i personally think that cowboy boots with shorts look great! in what cases do cowboy boots not look good with shorts?

  102. 102
    June 22nd, 2011 at 12:05 pm

    Thanks Gracie, I guess I was a little self conscious.

  103. 103
    June 22nd, 2011 at 1:00 pm

    Ur welcome :)

  104. 104
    June 26th, 2011 at 9:08 am

    I’ve been trying to find a cute pair of cowgirl boots but I’m not sure where I should get them from. I live in New York (originally from Kansas) and they don’t sell them anywhere up here. Does any one know of a website I can buy a pair? Thanks!

  105. 105
    July 19th, 2011 at 6:04 pm

    can you update this post? i still see cowboy boots all over nyc…still not sure if/how i can pull them off…thanks!

  106. 106
    July 25th, 2011 at 11:10 pm

    I LOVE Cowboy boots SO much! I’m sending this link to my mom actually cuz she thinks that what I wear them with is so silly :P I bought a pair of Justin boots this Spring and they go with almost literally EVERYTHING I own! I don’t own horses or live on a farm, just LOVE boots! :) I will wear them with almost any sundress I own, plus dressy, floral or jean mini skirts and shorts, and I’ll just pair that with any top I feel like! :) Jeans are great for colder weather (since I go to school in Moorhead, MN) My personal favorite for outfits is my Brown cowboy boots with white footless tights (pulled down far enough so you can’t see the bottom of the tights) along with a floral dress and skinny belt. I DEFINITELY have gotten LOTS of compliments on that outfit :) Plus, I tend to like to add my straw cowboy hat too and it’s still not over the top, but it looks cute for summer and is kinda country, but not TOO country :) THANK YOU for this website! :)

  107. 107
    July 29th, 2011 at 8:29 pm

    i honestly dont own another pair of shoes except flip flops and volleyball shoes i wear my cowboy boots with everything ive worn them with my bikini i wear them everyday and i dont care if im labeled the girl with the boots because im a cowgirl and thats who i am

  108. 108
    August 1st, 2011 at 4:09 pm

    I think cowboys boots are really cute! I’d probably wear them something like this: white tank top or t-shirt, black skinny jeans, white cowboy boots. Just seems to fit together nicely in my opinion.

  109. 109
    August 2nd, 2011 at 7:45 pm

    Your typical brown cowboy boots go well with olive colors, greys, and brown of course…Cargo shorts with cute vest and cowboy boots are very cute & chick, while also having an edgy appeal. When cowboy boots with a dress however, its best if the dress comes to your knees or no longer than midcalf

  110. 110
    August 12th, 2011 at 2:43 pm

    I so WANT those pink cowboy boots ! The heel on it is perfect. Anyway you can tell me where these might have been purchased ?

  111. 111
    September 8th, 2011 at 6:04 pm

    Does anyone wear cowboy boots with capris? What do you think? Can it be done? Or is that a no-no – capri’s & boots? Just wondering.

  112. 112
    October 28th, 2011 at 1:09 am

    I particularly like cowboy boots for women under the pants instead of outside. A good pair of boots will look good and be obvious without having to make it that pronounced, you know? Anyway…it’s great to see cowboy boots for women coming back as a fashion statement!

  113. 113
    February 27th, 2012 at 12:21 pm

    Can you wear brown cowboy boots with a long black western skirt and a white blouse?

  114. 114
    March 3rd, 2012 at 12:43 pm

    I live in Texas and cowboy boots are a MUST! They’re the cutest… year round!!! I personally have black ones and brown ones… I wear ‘em with my jeans, (under them) and with shorts whenever we go to a country bar… I swear you gotta wear shorts or a dress because country line dances get the whole place super hot!!!

  115. 115
    March 15th, 2012 at 2:08 pm

    I like western boots. It looks great on country look outfits! I gotta get red ish boots for my sundress.

  116. 116
    March 24th, 2012 at 1:20 am

    So, there are different styles of cowgirl boots and i’m not so sure mine work with a dress. I own the rounded toe boots, or riding boots. What should i do?

  117. 117
    May 17th, 2012 at 7:27 am

    I love my cowboy boots….!!!
    I live in mine everyday – i have a horse stud!
    And its so easy to just thrown on a nice dress and head to town! 4

    Love this blog

  118. 118
    September 28th, 2012 at 7:47 am

    I’m 55 and just bought a pair yesterday. It’s a great look if you have nice legs and knees. Great with skirts and skinny or boot cut jeans. Cute as h*ll, and I plan to ROCK THE BOOTS!!

  119. 119
    December 28th, 2012 at 10:51 am

    I agreed with most of this article until I got to the “How NOT to Wear Cowboy Boots”. You CAN wear them everyday if you want and you CAN where a country outfit with them especially if your from the south like me! Lastly, you can wear and over the top outfit with them depending on the occasion. Southern ladies love to be over the top and gaudy. ;)

  120. 120
    January 21st, 2013 at 10:53 pm

    I wish this trend would go out of style. For actual cowgirls like me, to see people wearing boots we work in and have to save up quite a bit of money to buy for the farm is distasteful. this is our way of life, not a fashion show.

  121. 121
    April 3rd, 2013 at 8:07 pm

    I like me my cowboy boots! I wear them about twice a week! I’m not known as “that girl with the cowboy boots”! I get a lot of compliments on them though. I typically wear them with jeans over top. I’m lookin for “that dress” so I can look fancy for a girls night out or somethin! I smile & laugh a little when I see someone in cowboy boots (not in a bad way!) I like that they’re expressin their country-ness!

  122. 122
    April 4th, 2013 at 6:52 am

    My outfit for the day: a plain purple loose fitting shirt (I think the color is plumb), dangley earrings, dark flare jeans, and cowgirl boots (with the jeans over the boots). Perfect! It’s simple, dressy, and makes a statement!

  123. 123
    April 6th, 2013 at 1:53 am

    I think cowgirl boots look good with jeans, shorts, and summer dresses. For me, anything else is weird. I think though if yo u are going to wear them with shorts your top should be very casual, minimal makeup, and god forbid no cowgirl hat!! To me, that gets very “Dukes of Hazzard”. But really, to each their own and wear them however you want. And I wear my boots everyday and there isn’t anything wrong with it.

  124. 124
    August 9th, 2013 at 9:29 pm

    I totally disagree…..cowgirl boots everyday is fine with me…I have quite a collection and I wear them how and when I want to…I just got back from spending a year in Branson and there are no rules there….you will see them everyday and everyway!

  125. 125
    September 2nd, 2013 at 1:52 pm

    Wearing cowboy boots ain’t supposed to be “cute”, they are to WORK in. To ride horses, to do DIRTY WORK they ain’t supposed to be a fashion statement they are for WORKING and hard labor.

  126. 126
    September 4th, 2013 at 6:00 pm

    I’m 57 years old and just bought my first pair of cowboy boots. Red studded Frye Billie style. The are FABULOUS and worth the wait!

  127. 127
    September 27th, 2013 at 1:33 pm

    It’s very trouble-free to find out any matter on net as compared to books, as I found this paragraph
    at this website.

  128. 128
    December 30th, 2013 at 2:49 am

    This is a great article.

    I think boots are from five years ago, are an old fashion.

  129. 129
    January 16th, 2014 at 5:06 pm

    I will wear my boots anytime

  130. 130
    January 19th, 2014 at 6:30 pm

    Always go for the brown boots

  131. 131
    March 29th, 2014 at 12:33 pm

    I bought my first pair today and I must say that your tips are priceless! :) a lot of ideas, photos – just love it! Unfortunately, here in Poland, people don’t wear this kind of shoes very often, so I couldn’t find any website with tips about cowboy boots. I hope it will change. Greetings!

  132. 132
    August 23rd, 2014 at 3:12 am

    Howdy I am so delighted I found your website, I really found you by accident,
    while I was researching on Yahoo for something else, Anyhow I am here
    now and would just like to say thanks for a fantastic post and a all round exciting blog (I also love the theme/design), I don’t have time to look over it all at the
    minute but I have bookmarked it and also included your RSS feeds,
    so when I have time I will be back to read a lot more, Please do keep
    up the great job.

  133. 133
    October 18th, 2014 at 7:15 pm

    For those who are asking either get a good brand at a thrift/resale store or go to cavenders you will be spending upwards of $100 but they will be comfortable and they will last you forever. I recommend Ariat they are very comfortable and affordable but the brand Corral has some more decorative boots that will look good with dresses but they are going to be more around $250

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