No Sandals in Sight: In NYC, This Is the Trendy Shoe People Are Wearing With Dresses and Skirts

Shop the comfortable, chic flats that well-dressed people are collecting.

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Katie Holmes wearing a red button-down, blue lace-trimmed dress, and black glove flats in NYC
(Image credit: T.JACKSON/Backgrid)
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I fully support people wearing whatever makes them comfortable, but I have to say that seeing very bare sandals (such as flip-flops, sorry!) on city streets makes me cringe a bit. It's exceedingly rare that I'll wear sandals at all when visiting NYC, especially after hearing a friend's story about a rat scurrying across her foot while waiting for the subway once. But alas, I'm not here to try to scare you away from wearing sandals in the city, but I am here to point out that there's an alternative, which happens to be a major 2026 flat-shoe trend that looks just as cool and seasonally appropriate with a dress or skirt as sandals do, and Katie Holmes just proved it. That trend is glove flats.

As a stylish resident of NYC who walks a lot, Holmes is a constant example of what to wear that's both functional and chic enough for the city. The outfit she chose for a recent outing was just that. Holmes wore a silky lace-trimmed Dôen dress (in the prettiest shade of blue imaginable), and instead of just throwing on a pair of sandals and heading out the door, she put on a red button-down shirt and the aforementioned glove flats. Soft leather ballet flats have a minimal look that subtly complements everything they're paired with, and they're comfortable enough to walk multiple blocks (yes, even avenues). They also add more of a cool-girl IYKYK look to an outfit than a simple pair of sandals might.

Now, if you don't own a pair of glove flats yet to wear with skirts and dresses (and everything else, of course), keep scrolling to pick your pair and to see Holmes' effortlessly chic spring dress outfit.

Katie Holmes Wearing a Dress + Glove Flats

Katie Holmes wearing a red button-down, blue lace-trimmed dress, and black glove flats in NYC

(Image credit: T.JACKSON/Backgrid)

On Katie Holmes: Dôen Marcelle Dress ($600)

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Allyson Payer
Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.