February 25, 2024

Few accessories can say that they’ve remained prevalent and stylish worldwide for as long as anyone can remember, but one — Converse’s Chuck Taylor sneaker — can, and it’s affordable, to boot. Celebs can’t get enough of the versatile sneaker, with everyone from Lady Gaga to supermodels like Gigi Hadid and Kendall Jenner sporting their pairs around town and on tour, and movie stars like Blake Lively wearing hers on the red carpet under a Prabal Gurung gown. At well over 100 years old and still relevant (they’re Timothée Chalamet’s red carpet fave, too), it’s safe to say that the classic sneaks are officially a wardrobe staple. Available in a wide range of colors, fabrics, and styles, including leather, platform, and high-top, there’s a Converse sneaker for every look.

Ready to give your Converse outfit a refresh? Keep scrolling for 16 upgraded takes on how to wear the legendary sneaker.

With a Suit

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Wearing sneakers with formal wear has been done on red carpets for years, and it definitely belongs in the boardroom, too. Whether you choose a classic black and white pair or one in a tone that coordinates with your suit, pairing your Converse with a two- or three-piece suit keeps you looking buttoned up while maintaining comfort and style.

With Cropped Pants

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If you own a pair of high-tops, try wearing pants that hit just above the ankle in order to properly show them off, or cuff a longer pair to achieve the same look. This works with jeans, khakis, or linen pants particularly well.

With a Maxiskirt

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Keep your full-length skirt from feeling too fancy by balancing it with sneakers that color coordinate with the rest of your look, or go with a pop of color peaking out from under the skirt’s hem.

With Some Tulle

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A vibrantly colored or sparkly pair of Converse will fall right in line with the whimsical vibe of a tulle or lace look. Want to amp it up even more? Consider a skirt or dress with a voluminous silhouette for maximum impact, and pair it with a cropped denim or leather jacket.

With Leather Leggings

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We love our leggings, but finding a comfortable shoe that dresses them up without looking out of step can be difficult. Converse sneakers perfectly walk that line between comfort and polish and get an extra boost from leather leggings in particular and a cozy sweater in a soft fabric.

With a Tracksuit

Yes, Converse is considered a sneaker, but it’s a little more elevated than your typical running shoe. On days when you’re leaning toward athleisure instead of activewear, finish off your tracksuit with a printed pick.

With a Sequined Gown

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If your goal is to make a glamorous gown work as an everyday outfit, dress it down and add some edge with a pair of Converse. Simple jewels and a small handbag will do the trick.

With Tights

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On chilly days, there’s nothing quite like slipping on a pair of sweater tights. Choose a high-top Converse and go the extra mile with a statement coat or jacket.

With Wide-Leg Trousers

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Lean into the ease of Converse with a wide-leg pair of trousers. From pinstripes to cargo styles and everything in between, a perfectly draped trouser over a pair of the classic sneaks is always chic, especially when paired with a simple top.

With a Blazer

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If you’re looking for an outfit that’s more casual than business but still looks polished, go for a blazer. Whether you pair it with jeans or slacks (or even a crop top), a blazer elevates your sneaks while still looking relaxed.

With Staple Pieces

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If you plan to stick with staples — a button-down shirt, a trench, black pants, etc. — continue the theme right down to your feet, choosing this timeless sneaker over bolder options.

With Oversized Pieces

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Converse aren’t as chunky as a pair of dad sneakers, so the slim fit helps to balance out baggy pants and jackets, and they’re especially well suited to highly layered looks that are heavy on the outerwear.

With Ankle Socks

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Tackle preppy style in a contemporary way by styling a denim, pleated, or leather skirt with a sweater, then complete the look with white Converse and delicate ankle socks. Add a button-down under your sweater to really kick the prep up a notch.

With a Leather Jacket

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A fool-proof outfit that’ll ensure you look badass and fashion forward every time? A leather jacket styled with black jeans and matching Converse.

With a Slip Dress

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Regardless of what you layer on top of a slip dress throughout the year, a pair of Converse will carry you through all four seasons.

With a Miniskirt

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Whether you choose a platform, high-top, or classic style of Converse, they’re unquestionably a great match for a swinging mini. Add sheer panty hose for a more dressy look, or go with bare legs for a more playful feel.