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.
Shop Moto Boots & Midi Skirts
The perfect weight and flare.
Three buckles, endless ways to wear.
This skirt is a top-seller at Uniqlo this season.
Level up with a slight platform.
Wool + cashmere = ultimate coziness.
Frye boots truly never fail.
Need to dress it up? Swap the moto boots for slouch stilettos.
An investment piece that you'll want to wear year after year.
When Stuart Weitzman boots are on sale, run.