There’s not a Y2K or ‘90s trend that hasn’t made its way back into the spotlight. From baggy jeans to baby tees to popcorn tops, it’s all come back around. Thankfully, each of these nostalgic styles gets a 2020s glow up before stepping into the time machine — because no one has time for their low-rise jeans to be literally falling off. Another early aughts staple ready for its resurgence? Western core. Specifically, cowboy boots. Of course, just like your parachute pants and dresses over jeans, there are ways to style cowboy boots that’ll still look like you’re living in this era.
“Looking at past trends and analytics and the fashion cycle in general, it makes sense that [cowboy boots] would be coming back around this time, especially in mainstream fashion,” Mikayla Stephenson, a fashion content creator, tells NYLON. “We've seen a lot of Western style lately, and nothing says Western more than cowboy boots,” she continues, noting the 20 to 30-year trend cycle. She points out a particular episode of Friends, in which Rachel talks to a trick-or-treater dressed as a cowboy. “And she was like, ‘Oh, I love your outfit, Western is so in,’” she recalls. “[Friends] was made in the late ‘90s [and] early 2000s, and we're seeing a lot of trends in general from that era come back,” she adds.
On top of that, style content creator Vanessa Chen points out the rise of various aesthetics following the 2020 lockdown. “[These styles] offer a kind of escapism where people can detach and express themselves outside of their current environment or situation,” she says, “Simply put, people just want styles that are fun, dramatic, and don't take themselves too seriously.” What’s 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 it more Hailey Bieber chic and less trick-or-treating cowboy from 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 chill, cool cowboy boot vibe is making its way to the scene. “They’re starting to be more casual and more of a staple piece than a statement piece,” she tells NYLON. “So a lot 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, effortless way, Stephenson recommends going for a look you could wear with sneakers, but then add a little spice with cowboy boots. For casual wear, she also suggests keeping the boots on the shorter side, like ankle or mid-calf height, and in colors like black or brown. “Having them be a little shorter and a little more muted definitely makes them a lot more casual,” she explains.
Social media fashion and lifestyle content creator Jolene Wright suggests kicking on the cowboy boots with a workout set and a blazer, button-up, or leather jacket. “I’ve also styled this look with both a button-up and a blazer over [the] top for additional textures and tones,” she tells NYLON, noting the added dimension and layering. “A baseball cap is another great accessory to add a fun, 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 go-to style is to pair them with a matching set or denim shorts, a simple tank, and throw a blazer over it all,” Toria Curbelo, a fashion content creator, tells NYLON. “That way it stays casual but has an elevated element to bring it all together.”
How To Wear Cowboy Boots For Going Out
There’s nothing like an LBD with a saucy pair of cowboy boots for a night on the town. This could be a sleek and elegant slip dress with tall black or white boots. “It's a little bit more streamlined, a little bit sexier as opposed to fun,” Chen tells NYLON.
Of course, the dress doesn’t have to be black. “If you want a little more of a statement, [choose something] a little more colorful — just a good, nice dress, maybe satin — and then pair it with more of a statement boot,” Stephenson offers, “something that typically would probably look very contrasting, but if you get the colors right, it can definitely dress it up 10 times more.”
As Curbelo puts it, 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 fringe or cutouts!”
For something a little more structured, go for mid-calf to tall cowboy boots with a smart, oversized blazer worn as a dress. “Even though on paper it doesn't really make sense, I think the juxtaposition of pairing something so sophisticated with something that's just really loud and eclectic is what makes it so fun,” Chen explains.
How To Wear Cowboy Boots With Pants
For a touch of that coveted street style aesthetic, introduce your cowboy boots to a pair of trousers and a blazer. You could even go for cargo pants because what’s more Y2K than that? “It’s a very simple, kind of slouchy outfit, but then the cowboy boots contrast it and bring in some different silhouettes,” Stephenson notes. “Cowboy boots in general are great to pair with contrasting styles or aesthetics because it creates its own aesthetic, but it's something that's still cohesive.”
Stephenson suggests jeans with a baggier fit, straight leg, or anything with a little slouch paired with a simple top. This could be a white button-up, scrunchy sweater, or clean layers like a tank top with a button-up blazer. For a more cohesive look, Stephenson recommends matching your top or outwear with the color of your boots.
Depending on the top and type of denim, jeans with cowboy boots can go casual, but can also be a little more dressed up. “Flares or a wide-legged silhouette would work better, that way you can tuck shorter cowboy boots underneath comfortably without any awkward bulging,” says Chen. Pretty much any top would go well, Chen says, but you might want to avoid blouses that tie in the front if you don’t want to go too Western. “A sleek bodysuit, a fun crop top, or a sweater — I think that could be fun,” Chen tells NYLON, suggesting playing around with the wash of your denim and color of boot.
How To Wear Cowboy Boots With A Skirt
Any length of skirt is a vibe with cowboy boots — it’s just a matter of how much you want to showcase the kicks. “If you want that effortless chic look, pair any kind of midi skirt with ankle to mid-calf styles, but avoid knee-high cowboy boots as they can look too bulky beneath the fabric,” Curbelo tells NYLON, adding that cowboy boots with satin midi skirts are very on trend right now.
According to Chen, flowier fabrics are the move with maxi skirts if you’re still trying to maximize air time on the boots. “That way, when you're moving and the skirt goes up a bit, you get little peeks,” she says. For the top, you could lean into the dreamy aspect of the skirts and take it in a cottagecore direction. “I really love the look of super romantic, billowy silhouettes with a pair of cowboy boots,” Chen says, “so like peasant sleeves, ruching, [and] tulle.”
If you’re going with 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 flavor, a simple top or layering with a blazer is also going to 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. Go all black or all white for a classy and coordinated effect.
How To Wear Cowboy Boots With A Dress
With dresses, the guidance is similar to that of skirts — only now you don’t even have to think about the top portion. 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 definitely could get away with the taller boot,” Stephenson tells NYLON. “Have the boot be more of a statement and just pair it with something super short, maybe super girly, simple, or contrasting, that makes the boots the focus of the outfit.” Again, to really streamline the ensemble, try coordinating the colors of your boots to any accessories you have, like a purse or handbag.
Just because you’re in a dress doesn’t mean the look has to feel dressed up. “Styling [cowboy boots] with a little sundress and out to lunch is a perfect casual look,” celebrity stylist and trends expert for DSW Dani Michelle tells NYLON.
How To Wear Cowboy Boots With Shorts
Shorts are definitely a moment for tall cowboy boots, but they can require a little more intention in styling. “You just need to be careful it doesn't get too costume Western-like,” Michelle points out. “For instance, jean shorts. I'd go black and city [style],” she offers. Bike shorts make for a contrasting aesthetic that can create a very cool-girl vibe as well.
You definitely don’t need to be afraid of denim shorts with cowboy boots, though. Chen suggests choosing an edgier top if you’re going with jean shorts “since denim is already super on the nose with the Western theme,” she tells NYLON. “Maybe an asymmetric crop top [as opposed to], like, a red gingham front-tie blouse or something,” she offers.
Of course, style is personal and it’s an expression of you. “There really aren't any hard rules when it comes to fashion,” Chen says. Have fun with it and wear whatever makes you feel good.
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