I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025

All summer, we've been charting the rise—er, drop?—in longer inseams. Bermuda shorts and, yes, even culottes have emerged as the go-to shorts style among the fashion and celebrity crowds. Across the board, shorts have been getting longer, but they've also curiously been getting shorter, too. For Gen Zers, in particular, it's all about micro-shorts—from Sabrina Carpenter's signature bloomers to Olivia Rodrigo's $53 Nordstrom shorts. What's even more surprising than the arrival of these tiny inseams amid so many knee-grazing ones is the shoes people are pairing with them.

As with any barely there trend, the general advice is to keep the rest of the look classic, but instead of pairing their shorts with a more obvious shoe choice like, say, sandals, they're reaching for boots. I'll admit that I always thought of wearing shorts with boots as a style "mistake" because the shoes aren't traditionally flattering, but I might be eating my words now that a wave of outfits have appeared that make the combo look admittedly very chic. Ahead, see all the ways celebs and fashion girls are wearing tall and mid-calf boots with their shorts (and actually pulling it off).

On Olivia Rodrigo: Edikted Twyla Polka Dot Shorts ($53); Frye Campus Knee High Boots ($498)

The only thing that makes Olivia Rodrigo's trendy polka-dot shorts better is the fact that she paired them sleek black knee boots for an outing in NYC, giving the shorts a cool spin for the city.

Reformation

Dusk Stretch Knit Top

EDIKTED

Twyla Polka Dot Shorts

Frye

Campus Knee High Boot

On Dua Lipa: Martine Rose T-shirt; Courrèges Americana Boots ($906); Chanel 25 Bag ($6000); Re/Done 90S Frayed Organic Denim Shorts ($288)

Denim shorts haven't been top of mind for me this summer, but as soon as I saw Dua Lipa styling hers with mid-calf moto boots, I realized it all comes down to the shoes. Her boots feel far fresher with cutoffs than the flip-flops or sneakers I'm programmed to reach for.

Sporty & Rich

Health Script Cotton Graphic T-Shirt

AGOLDE

Parker Long Shorts

Coconuts by Matisse

Autumn Engineer Boot

It's the summer of the outdoorsy-chic wardrobe, whether that be in the English countryside, Provence, or the Hamptons. Channel the energy of an off-grid escape when you pair welly boots with short shorts and a classic knit.