How To Wear Your High-Top Converse With Every Outfit

It’s a classic shoe for a reason.

In the era of microtrends, it’s enticing to want to participate in every exciting but ephemeral style movement that arrives, whether that’s snagging a pair of second skin knee-high boots, satin ballerina flats, or neon pink cowboy boots that you absolutely adore. Then, though, when the world moves on to a different shoe, you’ll likely tuck them away and let them gather dust until they inevitably come back into style. However, there are some shoes that you don’t need to patiently await the return of. Chuck Taylor All Stars are one of those timeless icons, and deciding how to wear high-top Converse with your personal fashion sensibility is as easy as putting on a plain white tee.

The power of the high-top Converse has endured ever since the original ancestor of the All-Star design was introduced in 1917 as a non-slip basketball shoe. Since then, the retro sneaker has become a mainstay in all-American style. “They have a timeless look,” style content creator Madison Loaiza-Brotherton tells NYLON. “They were the first ones to coin that iconic lace style and rubber toe combo. It’s also not particular to any age group — from infants to seniors, Converse can fit anyone’s style. They’re going to be trendy for as long as shoes are around.”

Making appearances everywhere from city streets to red carpets, high-top Converse fit seamlessly with any and every aesthetic: feminine, masculine, cottagecore, grunge, glam, emo, dark academia, It Girl, punk, indie sleaze — the list is never-ending. Point is, fans of Chucks are loyal to the shoe no matter their seasonal garb. “I think those who wear Converse don't care whether they are in or out of style, which is why they will never go away,” Melina Marissa, a digital fashion creator, tells NYLON. “They are just classics. Essentials. Been worn by so many types of people that they are past ever being a trend. They are just it.”

Like any other ageless accessory or piece of clothing, there are contemporary of-the-moment iterations of it on the style agenda at any given time. Right now, for example, platform high-top Converse are the en-vogue choice, as propelled by TikTok and Instagram trends. “I do think that Converse are particularly trending right now due to fashion trends being so pushed on social media,” style content creator Sierra Cannon tells NYLON, “but they definitely will last a lot longer than most trend cycles.”

The best part about Converse is that they are moldable to whatever aesthetic you wear, at any time of the year, which is why doling out fashion do’s and don’ts when it comes to Chucks isn’t really applicable. That being said, these are the ways fashion creators like to wear their high-top Converse sneakers, with shorts, skirts, trousers, tights, and more.

How To Style High-Top Converse With Shorts

Converse are an easy-going, easily adaptable shoe for day-to-day wear, so pairing them with shorts is a no-brainer. “I feel like Converse are meant for the warm weather; they are meant to be worn and used and really not supposed to be clean shoes,” Marissa says. “So I'd go with shorts and a tee or a dress! Literally whatever you fancy: little romper, overalls, a cargo skirt — it all works.”

Be it with denim shorts or bike shorts, Converse look great with pretty much any summertime bottoms. “I usually wear them with white socks and shorts,” says Marissa.

How To Style High-Top Converse With A Skirt

Another option for warm or transitional weather is pairing high-tops with a skirt. The best part? They’ll look great with any length: mini, midi, or poking out from underneath a maxi (and the same goes for dresses).

As one small style tip, Loaiza-Brotherton recommends wearing taller socks with high-top sneakers. Not only does it make your look more natural and pulled together, but it will also make things comfier, ensuring the canvas doesn’t irritate the back of your ankle. “My style advice for anything is do what makes you feel confident and comfortable, no matter the season or vibe,” Loaiza-Brotherton says. “There are no ‘rules,’ per se, but my favorite rule of thumb for any high-top is to make sure the sock shows above the sneaker.”

How To Style High-Top Converse With Pants

As for her favorite way to wear her high-top kicks, Loaiza-Brotherton says it’s nearly impossible to choose given how many different ways she styles them. But one of her go-to ways is pairing them with jeans or trousers, giving a more relaxed, even androgynous feel. “I really like playing off of The Outsiders/Ponyboy vibe when I style them,” she says.

One of Cannon’s go-to outfits, especially for sunnier weather, is a pared-down casual jeans look that’s finished off with a pop of color from her shoes. “My favorite way to style high-top Converse in warm weather is with a simple tank top, denim jeans, and a pair of colored Converse,” she says.

When it comes to wearing Converse with pants in the fall and winter seasons, just know that you’ll likely need to bundle your feet up when the weather gets chilly. Still, they’re just as versatile with cold weather outfits. “Honestly, Converse are not built for the cold — they will never keep your feet warm,” Marissa says, “but I'd say wear quarter or mid-calf socks and maybe some fleece-lined slush pants over top, with a baggy white tee and a hoodie to top it off.”

Another reason to wear Converse in colder weather: They’re incredibly easy to clean. Part of what makes them so popular is their utilitarian and sturdy canvas material, so if you splash your kicks with mud while running around on a rainy day, it’ll be no problem.

How To Style High-Top Converse For An Edgy Look

When it comes to edgier aesthetics (think: punk, grunge, emo, and goth), Converse are a popular go-to — just ask the pop punk artists of the last three decades. “There's really no limit to this aesthetic,” Marissa says. “If we're playing it simple and casual, I'd go with all-black Converse, brown baggy pants, maybe cargos, maybe corduroys, [and] then a nice graphic tee ... and obviously load on that chunky jewelry.”

As for Cannon, if she’s styling an edgier look, one of her favorite outfits “would definitely be a black lace top, black mini skirt, and some mesh tights.” This kind of look is right up the 2014 Tumblrcore soft grunge alley, which has recently been resurrected.

How To Style High-Top Converse For A Playful Look

A playful look is one on repeat for Loaiza-Brotherton, and Converse are a great option for adding to that light-hearted, fun aesthetic. “I also love to match the color of the shoes to a color on top, whether that’s the shirt, a bag, a scarf, sunglasses, hat, etc.,” she says. “Most importantly, have fun and express yourself! Test those limits!”

Color, especially in a playful monochromatic way, is a big reason why Cannon is a Converse girl. “One of my favorite things about Converse is that they have them in nearly every color,” Cannon says. “Fashion has always been a way for me to express myself, so I love incorporating color into my outfits in unique ways. My two favorite ways to style my Converse are either with a monochromatic look or using the Converse to add a pop of color to a simple look.”

How To Style High-Top Converse For A Soft Feminine Look

Even though Converse are often associated with hard-edged or relaxed street style aesthetics, feminine looks are just as achievable. Another one of Loaiza-Brotherton’s favorite Converse outfits is a “sweet, feminine girl-next-door look.” If anything, they add a cool, casual element to a hyper-feminine look. “Whenever I style high-top Converse, I like to play off of comfort and familiarity,” Loaiza-Brotherton says. “They remind me of innocence and play.”

One easy outfit formula for a soft feminine look is pairing Converse with “a dainty dress with some cute ruffle socks,” as Cannon suggests. In general, you can play on lighter aesthetics by choosing Converse that fit within that color realm. “When I think of soft glam, I see lighter pastels, cream colors, and maybe some sparkle, so I would go with lighter-style Converse,” Marissa says. Though it’s not typically her personal style, to make the sneakers go along with a more fem look, she would “find a colorful hand-painted fruit summer dress with a white base color, and wear cream Converse with ruffle trim socks and a hand-beaded bag that's champagne colored.”

How To Style High-Top Converse For A Going Out Look

Converse have not historically been considered a particularly luxe shoe. However, as with all sneakers, contemporary fashion has blurred the lines between casual and formal. When it comes to going out outfits, Converse have become a staple. And a simple way to elevate any shoe — sneaker or otherwise — is to pair it with an all-black outfit, which Cannon is personally a fan of.

Plus, going out looks totally depend on your vibe, so if Converse feel like the right move for you, there’s truly no reason not to throw them on and lace them up — even with a slinky dress fit for a cocktail lounge. “If you're dancing all night at an underground bar or your night out is going for a nice dinner or playing board games, your style is probably going to change,” Marissa says. “I think I'd personally wear red Converse and some jeans with a cute top and a pleather jacket, but my ‘going out’ [vibe] is very chill.”

Whether you’re dancing all night long, strolling the farmer’s market, going to a concert, or dressing up for dinner, high-top Converse will never let you down. Fans of Chuck Taylor All Stars swear by having them in their wardrobe forever — and it’s never too late to invest in the timeless retro icon.

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