Giddy-Up ‘Cause We Found the 16 Best Cowboy Boots for Women to Wear This Fall

How to Wear Cowboy Boots

They may not be as practical at first glance as our beloved Chelsea boot, but cowboy boots are not as intimidating as you might initially think. From cozy casual to formal elegance, cowboy boots have a certain versatility that make them, dare we say it, the Renaissance shoe. Don’t believe us? We’ve broken down eight ways to style your cowboy boots so you will never have to feel like the one trick pony.

1. Pair with a mini dress. We may be in denial that the summer suns have set for good this year, but that doesn’t mean your favorite seasonal pieces have to follow suit. We suggest pairing the traditional western style with dainty feminine cuts or bow embellishments for a fun juxtaposition.
2. Modernize vintage-inspired silhouettes. Vintage vibes have been spotted everywhere recently—from the streets of NYFW to the depths of our TikTok feeds, Bridgerton-inspired corsets and midi skirts are having a moment. Meld the trends for a stunning contrast between the delicate, lived-in pieces and the stiff boots.
3. Wear under maxi dresses or skirts. A chic and dramatic maxi dress or skirt makes for an unforgettable statement look—especially when paired with cowboy boots. Not to mention, it’s such a chic and easy outfit to throw on that will take you from that job interview to dinner date all in a day’s work.
4. Match them to your clothes. There’s nothing cooler than looking effortlessly put together, and these models know all the tricks. If you prefer a monochromatic, neutral look, this one is for you. Simplicity is key.
5. Don the blazer and shorts combo. If you want to look polished yet casual, pair your cowboy boots with an oversize blazer and longer jean shorts. Business on top, party on the bottom.
6. Layer under or over jeans. No need to break the bank to keep up with the trends. Grab your most lived-in pair of denim and toss on boots instead of sneakers. For a peek-a-boo ‘fit, wear your cowboy boots with your favorite puddle pants or tuck in your baggy jeans to really draw the eye towards your feet.
7. Couple with a leather trench. Complement the leather of the cowboy boot with that of a leather trench so you can give those leather blazers a break. We especially love how the hem of the trench coat hits right at the start of the cowboy boots.
8. Show off with a mini skirt. Brands like Mui Mui continue to favor the miniskirt look, and there’s no denying how fun it is coupled with cowboy boots. While we know this length can be totally daunting to slip on, follow the nine rules for wearing mini skirts to feel your most confident and look sophisticated.