Sorry, Sandals—*This* is the Shoe Trend Chic Girls in Their 20s Are Wearing With Dresses in 2026

Let Olivia Rodrigo show you the way.

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Olivia Rodrigo wearing a black spaghetti strap drop-waist summer dress with black motorcycle boots.
(Image credit: Splash)
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When I think of summer fashion, dresses and sandals are what typically come to mind, the slinkier and strappier the better. They're airy and easy, two qualities I look for whenever temperatures rise to peak-summer levels. Or, at least, that was my go-to pairing. In the lead-up to 2026, I've seen a few alternative shoe options that have me questioning my longtime allegiance to sandals, steering my footwear preferences toward another, less conventional shoe trend: moto boots. Apparently, chic girls in their 20s aren't loyal to sandals like I thought we all were, and when they're looking for shoes to wear with summer dresses, moto boots are the style they're grabbing right now—case in point: Olivia Rodrigo.

Rodrigo, who's gearing up to release her third album, You Seem Pretty Sad for a Girl So in Love, on June 12, was spotted in Barcelona this week shopping with friends ahead of a private concert she'll be performing at in the Spanish city. For the casual occasion, the 23-year-old wore a black drop-waist knee-length dress by a local Barcelona brand, Gimaguas, which she paired with Frye moto boots, specifically, the Campus 14L boots, Ray-Ban sunglasses, and a handbag from the Rixo x Dragon Diffusion collaboration. Everyone's talking about the bag in fashion RN, but it was her dress-and-boots combo that immediately caught my eye. Everyone expects people to style a summer dress like hers with flip-flops or strappy sandals, but her choice to trade them in for edgy boots made her look tenfold cooler and more interesting.

Olivia Rodrigo's Look

Olivia Rodrigo wearing a black spaghetti strap drop-waist summer dress with black motorcycle boots.

(Image credit: Splash)

On Olivia Rodrigo: Gimaguas Leila Dress ($265); Frye Campus 14L Boots ($298); Rixo x Dragon Diffusion Amoria Shoulder Bag ($390)

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Next time you're not sure what shoes to wear with a summer dress, especially if you want to stand out instead of fit in, try swapping out sandals for rugged moto boots à la Rodrigo. And don't worry about finding a pair. There are plenty of versions to shop below.

Shop Olivia's Outfit

Shop Summer Dresses and Moto Boots

Eliza Huber
Eliza Huber
Associate Editorial Director

Eliza Huber is currently the Associate Editorial Director at Who What Wear. She joined the company in 2021 as a fashion editor after starting her career as a writer at Refinery29, where she worked for four years. During her time at WWW, she launched Go Sports, the publication's sports vertical, and published four (and counting) quarterly issues tied to the WNBA, Formula One, and more. She also created two franchises, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter for WWW's monthly cover features; and reported on new seasonal trends, up-and-coming designers, and celebrity style.