Seasons come and go, but wardrobe staples? They're meant to last forever. Case in point: our favorite leather moto boots. They're the last thing we put into storage come spring, and the first to return to the lineup on the first day of sweater weather. They work with everything—not just jeans—and Emma Chamberlain made the case for pairing fashion's favorite footwear with an unexpected winter silhouette: an A-line wool midi skirt.

The multi-hyphenate Gen Z influencer and Stuart Weitzman ambassador was recently spotted in New York City with Tennessee-based musician Eden Joel, who is rumored to be her new boyfriend. Dressed for the season in black and shades of gray, the duo's understated fall style is worth replicating, particularly Emma's charcoal-colored skirt and knee-high biker boots.

As temperatures continue to drop, we've rounded up an assortment of black moto boots and gray skirts to mix and match as we head into the holiday season. It's an unexpectedly chic outfit formula that, if Chamberlain's past style has shown us, will keep trending well into 2027.

(Image credit: The Image Direct)Shop Moto Boots & Midi Skirts

MANGO Flared Midi-Skirt

The perfect weight and flare.

Stuart Weitzman Ren Knee-High Moto Boots

Three buckles, endless ways to wear.

Uniqlo Brushed Jersey Flared Skirt

This skirt is a top-seller at Uniqlo this season.

Steve Madden Everest Harness Boots

Level up with a slight platform.

Chinti & Parker Wool Cashmere Midi Skirt

Wool + cashmere = ultimate coziness.

Frye Kate Harness Boots

Frye boots truly never fail.

Rails Odita Midi Skirt

Need to dress it up? Swap the moto boots for slouch stilettos.

Miu Miu Harness Leather Boots

Brandon Maxwell The Miller Structured Virgin Wool Knit Skirt

An investment piece that you'll want to wear year after year.

Stuart Weitzman Chrystie Knee-High Moto Boots

When Stuart Weitzman boots are on sale, run.