Fashion Street Style 16 Elevated Converse Outfits That Look So Darn Good By Samantha Sutton Samantha Sutton Samantha is InStyle's senior fashion editor. She joined the brand in 2019 and oversees the site's fashion coverage, including trend reporting, fashion exclusives, celebrity style interviews, and Fashion Week coverage. InStyle's editorial guidelines Updated on October 5, 2023 @ 04:09PM Trending Videos Close this video player Photo: Edward Berthelot/Getty Images 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. 01 of 16 With a Suit Edward Berthelot/Getty Images 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. 9 Fresh Ways to Style a Suit This Season 02 of 16 With Cropped Pants Vanni Bassetti/Getty Images 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. 03 of 16 With a Maxiskirt Edward Berthelot/Getty Images) 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. 04 of 16 With Some Tulle Edward Berthelot/Getty Images 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. 15 Stylish Ideas on What to Wear with a Tulle Skirt 05 of 16 With Leather Leggings Christian Vierig/Getty Images 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. 06 of 16 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. Lindsay Lohan 07 of 16 With a Sequined Gown Daniel Zuchnik/Getty Images 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. 08 of 16 With Tights Daniel Zuchnik/Getty Images 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. 09 of 16 With Wide-Leg Trousers Edward Berthelot/Getty Images 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. The 16 Best Black Work Pants That Will Elevate Your Back-to-Office Wardrobe 10 of 16 With a Blazer Edward Berthelot/Getty Images 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. 11 of 16 With Staple Pieces Edward Berthelot/Getty Images 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. 12 of 16 With Oversized Pieces Edward Berthelot/Getty Images 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. 22 Unexpected Oversized Blazer Outfit Ideas That Score Major Style Points 13 of 16 With Ankle Socks Melodie Jeng/Getty Images 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. 14 of 16 With a Leather Jacket Edward Berthelot/Getty Images 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. 15 of 16 With a Slip Dress Christian Vierig/Getty Images 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. 16 of 16 With a Miniskirt Edward Berthelot/Getty Images 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.