Cowboy boots aren’t just for rodeos anymore—these timeless shoes have become a versatile wardrobe staple, perfect for creating casual and bold looks. As a mix of practical and trendy, cowboy boots are a fashion favorite that easily adapts to different seasons, settings, and personal aesthetics.
If you want to learn how to wear cowboy boots in new ways, read on to discover 12 Western-inspired outfits you can find on ThredUp.
Cowboy boots are a popular boot style with roots in the American West. While they were originally crafted for function, they’re often worn as a fashion statement today.
Characterized by tall shafts, slightly angled heels, and pointed or rounded toes, cowboy boots have a distinct style. They were designed with horseback riders in mind, offering leg protection and keeping the wearer’s heels in the stirrups. For easy movement on and off the saddle, these boots also have treadless soles.
Modern cowboy boots come in various materials, from classic cowhide to vegan leather and exotic options like alligator. Ornate stitching often reinforces the structure, making the shoes more durable and less likely to crease.
The cowboy boots you see today have evolved to suit a range of needs. Whether you’re strolling the city streets or riding a horse, these shoes are right at home.
If you’re wondering what to wear with cowboy boots, try one of these 12 outfits.
You can’t go wrong with a classic: pair medium-wash denim with a tucked-in pearl-snap shirt for a Western flair. To complete the outfit, add a leather belt with a subtle buckle and a wide-brimmed hat. Wear this combination for outings like weekend brunch or a stroll through the farmers’ market.
If you’re headed to a date night or casual party with friends, balance the rugged design of cowboy boots with the delicate touch of a slip dress. Choose black boots with a sleek leather finish and a lower heel to let the dress take center stage. To add a touch of sophistication, accessorize with an oversized blazer, simple gold jewelry, and a clutch.
Style cowboy boots with straight-leg jeans and a chunky knit sweater for a laid-back outfit. Light-colored footwear pairs beautifully with cream or pastel sweaters and light-wash denim. Add a crossbody bag and, if the weather is cool, a matching scarf. Wear this ensemble for everything from running errands to grabbing coffee with friends.
Elevate your cowboy boots with a leather skirt and fitted turtleneck. This sleek city outfit pairs well with pointed black boots, as this toe style adds an urban edge to your look. If you like to keep things monochrome, opt for all-black accessories, like tights, a handbag, and a jacket.
Channel your inner music festival-goer by pairing cowboy boots with a jean skirt and a vintage-inspired tee. Reach for boots with fringe, and tuck the shirt in. If you’ll be out late or the weather is chilly, layer with a flannel shirt or matching fringe jacket.
Snag a pair of brightly colored boots, then reach for a neutral-colored dress that hits just above the knee to show them off. For instance, a black sweater dress pairs well with red cowboy boots. Accessorize with a leather jacket or longline coat and a leather tote bag.
Once you’re dressed, head out to a dinner date on a chilly fall day or out to drinks with your friends.
Give a polished outfit a Western twist by pairing straight-leg trousers with a crisp button-up and cowboy boots. Stick to leather boots and a neutral top to keep things modern and sleek.
Accessorize this outfit with a slim belt and a structured blazer. For something more casual, swap the blazer for a fitted denim jacket.
Cowboy boots and a flowy maxi turn this classic footwear into a fun boho accessory. Choose a dress with a floral print and boots in rich brown leather. Alternatively, wear gray cowboy boots with a low-cut black maxi dress. Add a fringe jacket, a stack of bangles, and a clutch to tie the look together, and wear it to an informal outdoor wedding or garden party.
Show off your favorite pair of detailed cowboy boots with black skinny jeans. Choose footwear with something special, like a pattern, embroidery, or fringe.
Tuck the jeans into the shoes and add a simple white tank top and basic leather jacket to keep the focus on your footwear. To up the cool factor, add a statement handbag and oversized sunglasses. This edgy combination is ideal for city adventures and concerts.
If you’re wondering what to wear with country boots, reach for wide-leg jeans. Wear these bottoms over simple brown or black cowboy boots with a low heel and pointed toe. Pair these pieces with a fitted knit top or a tucked-in blouse to balance the pants’ volume.
This outfit is casual enough for running errands or meeting up with friends. On casual Fridays, accessorize with a blazer and a structured tote bag.
Lean into the Western flair with this outfit. Reach for fringed jackets, Pendleton-inspired tops, and bejeweled handbags. Of course, you can’t forget the cowboy hat! At the rodeo, more is more, so feel free to go wild with turquoise necklaces and chunky bangles.
If you’re headed to a Western-themed wedding, cowboy boots will be the footwear of choice. Pick a wedding guest dress that suits the code, and pair it with your favorite embellished boots. Add some turquoise accessories, and you’ll be ready to party!
Pro tip: Avoid white boots, as the bride might wear a pair, and you don’t want to upstage her.
Cowboy boots are a versatile addition to any wardrobe, and you can find the perfect pair on ThredUp. Whether you wear these shoes with jeans, dresses, or tailored pieces, they’re a great way to spice up your closet.
ThredUp has an extensive collection of shoes that go with everything, including preloved cowboy boots, winter boots, and Chelsea boots. 50,000 new items drop daily, so you can explore various designs that suit your aesthetic. And if you need fashion help, try our AI-powered Style Chat feature. Just describe a look, and the platform will show you items for sale so you can shop your ideas.
Elevate your wardrobe with cowboy boots from ThredUp—where style, savings, and sustainability come together.
Yes, you can absolutely wear short cowboy boots with leggings. Choose neutral-toned leggings like black, and add an oversized cardigan and a tank top to complete the look. Leather leggings elevate this outfit, especially with a fitted tank and plaid shacket.
This depends on the jeans and the outfit you’re building. Bootcut and straight-leg jeans are typically worn over cowboy boots, giving your outfit a traditional Western vibe. But skinny jeans can be tucked into the shoes to show off their details, like intricate stitching. Choose the one that best complements your outfit and the occasion.
To wear short boots with jeans, choose slim or skinny denim and tuck them into the shoes. But let the hem fall over the footwear if you’re wearing straight-leg or bootcut jeans. To complement your Western aesthetic, pair the pants with a cropped jacket and a tucked-in blouse or T-shirt.