How to Wear Converse in 2021 — And 2 Looks That Are Best Left In the Past

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Vice President Kamala Harris’s love of Converse sneakers is well-documented—she even wore them on the cover of Vogue (though that caused a bit of controversy)—but it wasn’t until the inauguration on January 20, 2021 that this classic shoe really started trending. What do we mean, exactly? There was a 233-percent increase in searches for Chuck Taylors the week of the inauguration, according to global shopping platform Lyst. For the event, Harris wore classic black pumps in place of her beloved kicks, but clearly her sense of style has had an impact on shoppers. So, inspired by the VP, we’ve rounded up nine sneaker-friendly outfits that are modern, fresh, mature (plus two that are best left in the past), all of which feature a pair of Converse Chuck Taylors. Now all we need is a string of pearls and we’ll be ready to dress like Harris every day of the week.

We Did Some Digging to Find the 15 Most Comfortable Sneakers Money Can Buy

how to wear converse sneakers with a suit
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1. sport A Suit

Perhaps the most “of the moment” way to sport classic Converses is with a suit, à la Madam vice president. These low-cut lace-ups easily tone down the seriousness of a tailored suit, but play with your choice of top, accessories, jewelry and hair to skew things more professional or ramp up the casual factor, as needed. Try a string of pearls, a button-down shirt and a structured handbag for a posh vibe, or a cowl-neck sweater or graphic tee and beachy waves for a low-key look.

Shop similar styles: J.Crew blazer ($198) and pants ($90); Banana Republic sweater ($99; $34); Saint Laurent bag ($1,290); Converse sneakers ($50)

how to wear converse sneakers neutral hues
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2. stick With Just Two Neutral Hues

We love a good monochrome ensemble, but a two-tone look can often be just as chic. Rather than sporting bold black and white, why not try something a bit softer, like white and beige or oatmeal and camel? Darker neutral pieces don’t need to match exactly (they just need to be similar) but try to get your whites to coordinate as closely as possible. Positioning a creamy winter shade next to a stark crisp white runs the risk of the warmer shade looking dirty.

Shop similar styles: Bille the Label coat ($378); Everlane top ($35); Nic+Zoe pants ($128); Converse sneakers ($55)

how to wear converse sneakers with an oversize sweater
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3. try An Oversize Sweater And Silky Skirt

Yes, Converse can work for your next date and this outfit is proof. Layer a slouchy sweater over a slinky silk dress or skirt (a thigh-baring leg slit is optional) and top it all off with some delicate gold or silver jewelry. The end result is all at once sexy, cozy and appropriate for anything from intimate cocktails to an afternoon museum visit.

Shop similar styles: Jackie Mack earrings ($63; $32) and necklace ($109); Line & Dot sweater ($69); Vince skirt ($225; $113); Converse sneakers ($55)

how to wear converse sneakers with colors
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4. take A More Colorful Approach To Monochrome

Converse sneakers come in such a wide range of colors, patterns and vibrant artist collaborations that it seems a shame not to take these pops of fun and run with them. You don’t need to get too crazy about finding an outfit that perfectly matches your teal tie-dye kicks, but to nail the monochrome thing, you’ll want to choose pieces that fall within the same color family and that either all lean toward the cool or the warm end of the spectrum. (Bonus points if your face mask also fits in with the theme.)

Shop similar styles: Rachel Silk face mask ($17); AMI Paris sweater ($365); A.L.C. pants ($395; $98); Converse sneakers ($75)

how to wear converse sneakers with textures
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5. or Play Around With Textures

Similarly, there are also a ton of interesting non-canvas or leather materials to choose from for your next pair of kicks. Chambray denim, faux-fur, corduroy and even duvet-inspired quilting have been used by Converse to liven up its OG Chucks. Consider repeating the texture or material of your shoes someplace else in your outfit to link them together without looking too matchy-matchy.

Shop similar styles: Soia & Kyo coat ($645; $387); Converse sneakers ($85; $40)

6. offset A Flirty Minidress

In the same way that lace-up sneakers can tone down the board room vibes of a tailored suit, high-tops can also make a ruffled, super-feminine minidress feel less overtly sexy. Take inspiration from Coterie member Caroline Juen and keep the rest of your ensemble fairly simple—easy low ponytail, simple black handbag, a red lip—to create an outfit that will work for just about any plans you have this weekend.

Shop similar styles: Billabong dress ($60); Converse sneakers ($55)

how to wear converse sneakers with a dress
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7. or A Voluminous Midi

Similarly, a pair of casual Chucks can make a flouncy prairie or nap dress feel less like you’re playing dress up in the closet of your nine-year-old niece. Choose sneakers in the same or a very similar shade to your frock and continue mixing and matching your accessories—delicate gold chains or pearls with sporty touches, like Wayfarer sunglasses or a mini backpack—and you’ll soon see these opposites do, in fact, work quite well together.

Shop similar styles: Merlette dress ($420); Sonia Rykiel bag ($400; $240); Converse sneakers ($55)

how to wear converse sneakers with a sweater dress
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8. or Even A Form-fitting Sweater Dress

A curve-hugging knit dress, however trendy, may feel a bit too sexy for everyday wear. But add on an oversize blazer and some comfy kicks, and you’re singing a totally different tune. This single-tone outfit does a really stellar job of dressing up these sneakers—even if they are a little mussed up and dirt-streaked.

Shop similar styles: Vince blazer ($495); NBD dress ($140); Converse sneakers ($55)

how to wear converse sneakers with jeans
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9. wear Ankle-grazing Jeans

The best jeans to wear with Converse in 2021 are those that hit right above the ankle in a straight-leg cut (or maybe a cropped wide-leg). They give some shape and definition to your legs without turning them into bean poles (as skinny jeans are wont do) and the slightly cropped length allows your hi-tops to truly steal the spotlight. If you’re feeling festive, pull on a pair of boldy colored or patterned socks to peek out between your shoes and jeans. Otherwise, stick to classic white or black and opt for a fitted pair rather than anything slouchy.

Shop similar styles: Topshop jacket ($95); Nicholas sweater ($245); Vero Moda jeans ($85; $47); Converse sneakers ($55)

how to wear converse in 2021 dont 2
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10. don’t Go Too Oversized Or Too Distressed

A loose-cut jacket, oversize button-down and baggy, distressed boyfriend jeans don’t work well together, regardless of what shoes you have on. But adding Converse into the mix just solidifies this as a ‘90s alt-rock costume rather than a modern or trendy ensemble. Just a simple swap or two—try straight jeans and an oversize blazer—are all you need to reclaim some semblance of a silhouette and return to the 21st century.

how to wear converse in 2021 dont 1
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11. Don’t Skew Too Playful

Polo shirts, canvas tote bags and denim shorts all evoke images of summer camp, which is nice to think back on but not exactly the best sartorial choice for a full-grown adult. Much like the outfit above, there are a handful of simple tweaks that will make this outfit shine: replace the canvas tote with a leather or suede style instead, switch out denim cut-offs for cropped wide-leg jeans and your collared tee for a simple white style. Even making just one of these changes will greatly improve your look (although we strongly recommend considering them all).

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Abby Hepworth


Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...
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