Your 2020 Comfy-Shoe Directory: 5 Trends to Wear Now and Next Year

There’s a common misconception that you must sacrifice style if you want to wear an actually comfortable pair of shoes. That couldn’t be further from the truth. While we recently covered a range of fresh footwear picks that won’t give you pain, the S/S 20 runways were filled with a smattering of new shoe trends that could easily rival even your comfiest pair of sneakers.

To highlight further, we curated the ultimate 2020 comfy-shoe directory for you below with the functional yet fashionable silhouettes you’ll see everywhere in the next six months. So with that, keep scrolling to uncover the most practical low heels, flats, and more with street style and runway inspiration. And because we know you won’t want to wait until next year to test out these comfortable shoe picks, we shopped out current iterations so you can get a jump start on the action.

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(Image credit: Prada/Pietro D'aprano/Getty Images; Daniel Zuchnik/Getty Images)

Loafers hit the mainstream a few seasons ago and will continue to make even greater waves next year with the addition of comfy block heels in mixed textures. There’s no doubt fashion girls will clamor for this silhouette for its comfortable yet chic nature.

Shop the trend:

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(Image credit: Chanel/Peter White/Getty Images; Edward Berthelot/Getty Images)

Anna Wintour recently named flat shoes as the must-have silhouette of 2020. We’re so here for it—especially the comfortable, elegant, and highly versatile flat Mary Jane styles that are dominating the runways and the streets.

Shop the trend:

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(Image credit: 3.1 Phillip Lim/Peter White/Getty Images; Edward Berthelot/Getty Images)

Get ready. Birkenstock-esque sandals are here to stay. While they're polarizing in nature, we’re all for the style to bring comfort and ease into any look. Try them with socks and your favorite jeans and sweater, or dress them up with a suit or formal ensemble for an unexpected yet extremely fashion-forward vibe.

Shop the trend:

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(Image credit: Matty Bovan/Victor Virgile/Getty Images; Christian Vierig/Getty Images)

A chunkier sole is inherently more comfortable than a style with limited support (ahem, stilettos). Enter the flatform. Next year will be all about the updated flat platform silhouette in both multicolored hues and neutral styles with statement details.

Shop the trend:

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(Image credit: Arthur Arbesser/Victor Virgile/Getty Images; Edward Berhelot/Getty Images)

Whether you used to love or loathe them, clogs will be sticking around next year as the coolest alternative to the standard booties you’ve been wearing for comfort. While solid clunksters will dominate, styles in unexpected animal prints will keep the "ugly” shoes feeling fresh and pretty.

Shop the trend:

Next, check out the outdated winter boot trends we won't be wearing this season.

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retialers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.