How to Wear Cowboy Boots With Any Aesthetic


There isn’t a trend from the year 2000 or the 90s that hasn’t come back to the fore. From baggy jeans to baby t-shirts to popcorn tops, it’s all back. Luckily, each of these nostalgic styles gets a 2020s glow before entering the time machine — because no one has time for their low-rise jeans to literally fall off. Another early 2000s staple ready for a resurgence? Western core. Specifically, cowboy boots. Of course, just like your parachute pants and dresses over jeans, there are ways to wear cowboy boots that will still feel like you’re living in that era.

“Looking at past trends and analysis and the fashion cycle in general, it makes sense that [cowboy boots] would come back to this era, especially in mainstream fashion,” fashion content creator Mikayla Stephenson told NYLON. “We’ve seen a lot of western styling lately, and nothing says western more than cowboy boots,” she continues, noting the 20-30 year trend cycle. It signals a particular episode of Friends, in which Rachel talks to a deceiver dressed as a cowboy. “And she was like, ‘Oh, I love your outfit, Western is so trendy,'” she recalled. “[Friends] was made in the late 90s [and] early 2000s, and we see a lot of trends in general from that era coming back,” she adds.

On top of that, style content creator Vanessa Chen highlights the rise of various post-lockdown aesthetics in 2020.”[These styles] offer a kind of escape where people can detach and express themselves outside of their current environment or situation,” she says, “Put simply, people just want styles that are fun, dramatic, and don’t get caught not too seriously. What could be more fun and dramatic than a pair of boots made for walking?

As playful and trendy as they are, they can be an intimidating piece to style. What are you supposed to wear with cowboy boots? How do you keep Hailey Bieber more chic and less of a deceitful cowboy? Friends? The style gurus have you covered, below.

How to Wear Cowboy Boots for a Casual Look

While a good, statement boot look will forever sit high on the pedestal, Stephenson notes that a cool, cool cowboy boot vibe is making its way to the scene. “They’re starting to be more laid back and more of a staple piece than a statement piece,” she tells NYLON. “So much more subtle and worn in place of pretty much any other black bootie or basic boot,” she explains.

To rock your cowboy boots in a more understated and effortless way, Stephenson recommends opting for a look that you could wear with sneakers, but then add some pizzazz with cowboy boots. For casual outfits, she also suggests keeping boots on the shorter side, like ankle or mid-calf height, and in colors like black or brown. “The fact that they’re a little shorter and a little more low-key definitely makes them a lot more laid-back,” she explains.

Jolene Wright, a fashion and lifestyle content creator on social media, suggests wearing cowboy boots with a workout ensemble and a blazer, button-down or leather jacket. “I also styled this look with a button up and a blazer over it [the] top for extra textures and tones,” she tells NYLON, noting the extra dimension and layering. “A baseball cap is another great accessory to add a fun and sporty element to the casual look,” she continues.

As for the rest of the fit, jeans or shorts are a great place to start if you’re trying to keep it NBD. “My favorite style is teaming them with a matching set or denim shorts, a simple tank top and throwing a blazer over it,” Toria Curbelo, a fashion content creator, says NYLON. “That way it stays laid back but has an elevated element to bring it all together.”

How to wear cowboy boots for going out

There’s nothing quite like an LBD with a pair of cowboy boots for a night out on the town. It could be a sleek and stylish slip dress with tall black or white boots. “It’s a little more streamlined, a little sexier than it’s fun,” Chen told NYLON.

Of course, the dress doesn’t have to be black. “If you want a little more of a statement, [choose something] a bit more colorful – just a good, nice dress, maybe satin – then pair it with a more assertive boot,” Stephenson suggests, “something that would probably look very contrasting, but if you get the right colors, it can definitely dress it up 10 times more.

As Curbelo says, anything short or sparkly with cowboy boots is sure to get the job done when you’re feeling extra. “Even more points if it also has fringes or cutouts!”

For something a little more structured, opt for mid-calf to high cowboy boots with a sleek, oversized blazer worn as a dress. “Even though on paper it doesn’t really make sense, I think the juxtaposition of pairing something so fancy with something really loud and eclectic is what makes it so fun,” says Chen.

How To Wear Cowboy Boots With Pants

For a touch of that coveted street style aesthetic, pair your cowboy boots with pants and a blazer. You could even opt for cargo pants, because what’s more Y2K than that? “It’s a very simple outfit, quite loose, but the cowboy boots contrast it and bring in different silhouettes,” notes Stephenson. “Cowboy boots in general are great to pair with contrasting styles or aesthetics because they create their own aesthetic, but it’s something that stays consistent.”

Stephenson suggests jeans with a looser fit, straight legs, or anything with a bit of slack paired with a simple top. It can be a white button down jumper, a scrunchie or clean layers like a tank top with a button up blazer. For a more cohesive look, Stephenson recommends matching your top or outerwear to the color of your boots.

Depending on the top and type of denim, jeans with cowboy boots can be casual, but can also be a little dressier. “Flares or a wide-legged silhouette would work best, that way you can comfortably tuck shorter cowboy boots underneath without any annoying bulges,” says Chen. Just about any top would be fine, Chen says, but you might want to avoid blouses that tie in the front if you don’t want to go too western. “A stylish bodysuit, a fun crop top or a sweater — I think that could be fun,” Chen told NYLON, suggesting playing around with your denim wash and boot color.

How To Wear Cowboy Boots With a Skirt

Any skirt length is a vibe with cowboy boots – it’s just a matter of how much you want to show off the kicks. “If you want that effortless chic look, pair any type of midi skirt with mid-calf ankle styles, but avoid knee-high cowboy boots as they can feel too bulky under the fabric. “, Curbelo told NYLON, adding that cowboy boots with satin midi skirts are very trendy right now.

According to Chen, flowier fabrics are the way to go with long skirts if you’re still trying to maximize air time on boots. “That way when you move and the skirt goes up a bit, you get little peeks,” she says. For the top, you can lean on the dreamy look of skirts and take it in a cottagecore direction. “I really like the look of the super romantic, puffy silhouettes with a pair of cowboy boots,” Chen says, “like the peasant sleeves, the ruching, [and] tulle.”

If you go for a shorter skirt, you can get away with much taller boots, according to Curbelo. “Knee-high styles pair so well with pleated skirts for a feminine look [and] mini skirts for a Y2K aesthetic,” she says, adding that a cargo skirt for fall creates “the perfect street style look.”

If that’s not your taste, a simple top or layering with a blazer will also be a certified look with a skirt and cowboy boots. Even more so when the boots match your jacket, top or handbag, according to Stephenson. Opt for all black or all white for a classy and coordinated effect.

How To Wear Cowboy Boots With a Dress

With dresses, the advice is similar to that of skirts – only now you don’t even have to think about the top part. Again, Chen vibes with cottagecore silhouettes and fabrics when it comes to pairing dresses with cowboy boots, which works especially well for maxis and midis.

“With shorter dresses, you could definitely get away with the taller boot,” Stephenson told NYLON. “Make the boot more of a statement and just pair it with something super cropped, maybe super girly, plain or contrasting that makes the boot the center of the outfit.” Again, to really streamline the ensemble, try to color coordinate your boots with any accessories you have, such as a purse or purse.

Just because you’re wearing a dress doesn’t mean the look has to be dressed up. “Styling [cowboy boots] with a little sundress and going out to lunch, it’s a perfect casual look,” celebrity stylist and DSW trend expert Dani Michelle told NYLON.

How To Wear Cowboy Boots With Shorts

Shorts are definitely a time for tall cowboy boots, but they may need a little more intention in style. “You just have to be careful that it doesn’t get too western costumed,” Michelle points out. “For example, denim shorts. I would go black and city [style]“, she offers. Bike shorts offer a contrasting aesthetic that can also create a very cool girl vibe.

You definitely don’t need to be afraid of denim shorts with cowboy boots, though. Chen suggests going for a bolder top if you’re going for denim shorts “since denim is already super on the nose with the western theme,” she tells NYLON. “Maybe an asymmetrical crop top [as opposed to]like, a red gingham tie-up blouse or something,” she suggests.

Of course, the style is personal and it is an expression of you. “There are really no strict rules when it comes to fashion,” Chen says. Have fun with it and wear what makes you feel good.

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