Reminder: This Is the Only Winter Shoe Trend That Doesn't Look Odd With Bare Legs

By Swedan MargenNovember 17, 2025

Wearing a short dress in the winter may seem counterintuitive, especially if you live in a northern region or colder climates in general. Personally, I was initially hesitant about wearing a short dress at the start of winter in NYC, but my mind was changed, and one particular outfit (and shoe, specifically) inspired that shift. While attending GQ’s annual Man of the Year afterparty, Willow Smith was spotted wearing a black long coat layered over a mini sweater dress, paired with black square-toe knee-high boots. Baring your legs can look a bit odd in the winter, but the exception is when you wear a short dress, skirt, or shorts, with knee-high boots, which obviously leave less skin exposed than any other shoe style.

The full look embodied “quiet luxury” in a cool-girl kind of way. Smith made the sweater dress look elegant, rather than frumpy, with the addition of the sleek, long coat and her leather boots. This is going to be my new winter uniform, mark my words. I’m always going for a laid-back, cool vibe with my cold-weather outfits, in particular, and this one is just that.

If you’re into the idea of wearing a short dress while still looking put-together, keep scrolling to shop Smith’s outfit and similar items.