Reminder: This Is the Only Winter Shoe Trend That Doesn't Look Odd With Bare Legs
Don't worry. You won't be that cold.
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. One particular outfit and shoe style inspired that shift. While attending GQ's annual Men of the Year after-party, Willow Smith was spotted wearing a black long coat layered over a sweaterdress and 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 embodies quiet luxury in a cool-girl kind of way. Smith made the sweaterdress look elegant, rather than frumpy, with the addition of the sleek long coat and 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, 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.
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Kerane Marcellus is a New York-based writer. She joined the Who What Wear team in 2025 after writing for Essence Magazine and freelancing for a number of other arts and culture publications. Fashion is a form of expression that she encourages everyone to take part in. There is no right or wrong in getting dressed! When she's not writing, she's reading in the park or gallery hopping in the city.
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