5 Winter Skirt Trends Everyone Is Wearing With Boots in 2026 Leave a comment

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.