5 Winter Skirt Trends Everyone Is Wearing With Boots This Year

Trust me, It girls everywhere are wearing them.

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women wearing skirts and boots
(Image credit: @sobalera; @_imanirandolph; @kelseymerritt)

I wear pants throughout the year almost exclusively, but the rest of this winter, I’m venturing out of my comfort zone by trying some skirt trends to wear with my usual boots-and-sweaters uniform. Skirts are one of those easy pieces you can implement into your wardrobe, even when it’s below freezing. Trust me, I’ve seen fashionable New Yorkers step out in chic and elegant outfits wearing various skirt trends. I’ve scrolled through Instagram and Pinterest for further outfit inspiration and noticed these types of outfits keep coming up with the same skirt trends.

NYC fashion people have been big fans of the leather skirt and other skirt styles like midi and, recently, low-rise skirts. These skirt trends all have one thing in common: timeless silhouettes. Each of them has a simplicity to it that is easy to style in various, fashionable ways. Gone are the days of looking frumpy during winter. I’m opting for chicer outfit options, and these skirt trends are the route. Other styles like knee-length skirts and pleated skirts are both classic shapes, but the IG fashion crowd is rediscovering them and turning them into the next winter It trends, and I couldn’t be more excited.

If you’re on the hunt for new bottoms to wear with your boots, keep scrolling to shop these not-so-new winter skirt trends.

Leather Skirts

a woman wearing a red sweater, black leather skirt, and black boots

(Image credit: @sobalera)

Knee-Length Skirts

a woman wearing a black sweater, plaid skirt, and black boots

(Image credit: @_imanirandolph)

Low-Rise Skirts

a woman wearing a black t-shirt, black low-rise skirt, and black boots

(Image credit: @anaasaber)

Pleated Maxi Skirts

a woman wearing a green trench coat, mustard blazer, plaid skirt, and boots

(Image credit: @lucyraemcfadin)

Midi Skirts

a woman wearing a black leather jacket, black skirt, and black boots

(Image credit: @kelseymerritt)
Kerane Marcellus
Associate Fashion Editor

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.