How to Wear Cowboy Boots (The Best Styling Ideas & Tips)

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Cowboy boots

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

Woman feet wearing Cowboy Boots With Jeans
Boots via Princess Polly

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

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

Woman feet wearing 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 Free People or Urban Outfitters. 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

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?

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72 thoughts on “How to Wear Cowboy Boots (The Best Styling Ideas & Tips)”

  1. 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. =]

  2. 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.

  3. 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

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  5. 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!

  6. 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!

  7. 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. 😉

  8. 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”. 🙂

  9. 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!

  10. 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!!!

  11. 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 ???

  12. Maybe you could change the blog title How to Wear Cowboy Boots &#8211 College Fashion to something more generic for your subject you make. I loved the blog post all the same.

  13. 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?


  14. 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!

  15. 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!

  16. 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.


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