Womens Cowboy Boots: Add a Cute Western Feel to Your Chic Outfit

I personally like the look of womens cowboy boots because they’re fun and adorable! Even though there are some people (especially hardcore Harper’s Bazaar and Vogue readers) who will claim that womens western boots aren’t ‘in’ or that they’re too ‘barnyard-ish’, I still believe that as long as you like them and make sure you wear it the right way, you’ll rock them!

Frye womens cowboy boots

The fab thing about cowboy boots is that they’re usually forgiving on muscular and thick legs because the shaft is wider than most average womens fashion boots.

Now before we dive into the glorious selection of womens cowboy boots, let’s take a moment and look at some outfit ideas and style tips on how to wear them!

How to Wear Womens Western Boots


I’m a firm believer in showing off your cowboy boots instead of hiding them underneath a long dress or wide leg jeans. What’s the point in wearing them if people will only see the tip of the boots instead of the beauty of the classic western boot shaft?

Womens cowboy boots outfit with jeans

Since the boots are usually wide around the leg they’ll look good with your skinny jeans or any tapered-cut pants. Straight-cut leg will work too, especially if you have thin legs and want to fill them out a little in these type of boots. Try out this look with a simple leather jacket and a structured handbag to tone down on the country vibe.

I personally wear my rounded-toe cowboy boots with skinnys and a comfy knit sweater.

fashion tip Note: Avoid going denim from top to toe with western boots. Denim on denim isn’t a faux paux anymore, but topping it off with a pair of cowboy boots is stretching it a bit!


I love this look 🙂 I know that Britney Spears has been giving this look a bad rep with her mini dress and messy hair, but we’re not doing the Brit style. Wearing them with a dress is a super-cute way to wear women’s cowboy boots, given that you’re wearing the right dress style and accessories to go with them.

Womens cowboy boots outfit with a dress

A chic way to wear the boots is with a solid-colored flowy, loose and/or casual dress, or a juxtaposition of the trendy boots. For example, boho, romantic or classy.

If you’re fashion-adventurous then you can take it up a notch with a bright colored dress. Also if you’re going the colorful way, you should keep it tasteful with a right above the knee, not mini.

fashion tip Note: If you decide to wear a colorful dress with the boots I would advise you to refrain from matching the outfit completely (eg. Brown boots with brown bag and brown belt) because it’ll magnify the western boot look. A matching outfit is generally a chic way to wear clothes but in this case, the boots and the dress will do A LOT of the talking 😉

Wearing the boots with a classic and simple dress is also another way to rock the look. Rachel Bilson is a perfect example of how fab you can look by pairing bright colored cowboy boots and a black dress.

For colder fall and winter months, a pair of western boots will go with a casual turtleneck dress and opaque or wool tights, or with a knit tunic top or sweater.


Short shorts, that is 😉 But not the skimpy ones that show off your butt cheeks! This is a great combo for elongating your legs and showing off their tan.

Womens cowboy boots outfit with shorts

If your legs aren’t your best asset (they’re short and not-so lean), then cover them up with black pantyhose or opaque/wool tights. I personally pair them with my distressed denim shorts, black tee and wrap cardigan.

fashion tip Note: Avoid the too-sexy Daisy Duke look by selecting a pair of womens cowboy boots in a simple style and pair the shorts with a loose-fitted top. Of course, a fitted tank top is ok but you might want to add a flowy vest or an unbuttoned shirt to balance it out a little.

More Style Tips on How to Wear Womens Cowboy Boots

  • Simple womens cowboy boots in neutral colors (black, tan, dark brown, beige) go with anything.
  • Keep the rest of your look simple. Let the boots be the focus. If you pair them with a colorful dress or a plaid shirt make an effort to keep the bottom and accessories simple.
  • Don’t wear them every day. Western boots give a maximum style impact if worn once in awhile. Trust me on this. You don’t want to be branded as that girl with the cowboy boots…
  • Never wear them with a cocktail dress, unless you’re Taylor Swift… or a country singer (entertaining us is what they do)

More fashion advice on Shoes:

Shop Latest Womens Cowboy Boots

Now, finally here are some western inspiration for you city-chic gals looking to unleash your Daisy Duke fashion moment!

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