How to Wear 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
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
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
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
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
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
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: Boots, Celebs, How To, Shoes
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Ashley
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!
Alyssa
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 :)
Alex
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.
lauren
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” !:)
xoxo
Zephyr
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!
kpriss
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!
Zephyr
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!
kristy
do you know where to buy some reasonably priced ones?
mcollazo
I like the idea of wearing them with a flowy dress, but can you wear this look/shoe for the spring?
shayne
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! :)
mr
Cowboy Boots With Dresses is one of the ugliest fashion statements ever!
ms
mr is a retard. sorry.
cowboy boots with anything is adorable.
Ali
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. =]
Deb
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.
Jaime
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,
http://www.thetrafficdriver.com/apparelaccessories.php – Your source for all things fashion
William
Hi,
I would love to sponsor this page. My website is http://www.bootcity.com/
please email if you are interested.
Bill
KC
Hey,
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!
ria
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!
Nicosha
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! :)
Kelley
Hey!! Thank you for all the ideas!!! If anyone is looking for a dress or boots, try http://store.delias.com/item.docategoryID=416&itemID=51098&sizeFilter=&colorFilter=&brandFilter=&CROSS=156051&i=155860
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:)
Kelley
Okay, sorry, the link didn’t work, but here are instructions to the site:
1. http://www.delias.com
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:))
Kim
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?
theresa
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?
Lauren
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…
Myra
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.
Venus
: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…
Joe
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.
Vintage Rolex Dude
amazing stuff thanx :)
Taylor
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.
Zephyr
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 :)
Gwen
How old is too old to wear cowboy boots with a dress??
Skylar Morton
Nice. Banger > Taylor Swift + Mom Jeans
Amile
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!
Nicole
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!
Kassie
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.
Lo
Nicole,
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.
Kassie,
I agree with you and I love the whole sundress and cowboy boots together!
Lo
Gwen,
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.
Hailey
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!
Hailey
I like the ones in the picture above, if they were brown. Where are those from?
Rebecca
Hailey,
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:
-www.shoes.com
-www.Zappos.com
-www.aldoshoes.com
………………………………………………………………………………………………………………………………
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?
Ella
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.
:)
Tara
Hey…
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:
http://www.shoe-envy.co.uk/Bronx_Dinus_Cowboy_Boots_Low_p350.html
Olivia
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
David
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.
Gabbie
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.. :/
Chata
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?
Kilianetreyon
hey i love them tooo but this is gay
Debbie F.
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!! :(
CAN ANYONE HELP??!
Mel
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.
Gale
Hi! great website just what i was looking for. Thank you x
Tiffany
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-
http://www.rockytopleather.com/categories/womens-old-gringo-boots/
Breanna
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.
posh
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.
Michelle
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!
Rachel
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!
Melissa
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!
lily
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.
Jennnifer
Jessica Simpson has some really cute cowgirl boots on her website!!!
Betty
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!!!!!
GABZ.
So.. Reading through this artical I read about not wearing plaid with it..
Have a question… Would this be.. “Socially” Acceptable..?
Boots: http://www.sheplers.com/womens/slouch_boots/045a33.html (black)
Shirt: http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=top&product%5Fid=2075656446&showBACK=OK (Mine is black & red)
Jeans: http://www.ae.com/web/browse/product.jsp?catId=cat90120&productId=0432_7756
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…..