Cowboy Boots

I have a pair of cowboy boots that I love. Here are the rules on how to wear them well and a list of how not to wear them

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!

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!

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.

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.

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.

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.


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?