30 Maxi Skirts I'll Gladly Want to Wear With Boots This Winter

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(Image credit: @CHLOEPIERRELDN)

While most people might wait for the spring or summer to pull out their favorite long skirts, I get the most wear out of mine in the colder months simply because of one styling cue—pairing them with boots. Once I started wearing the outfit combo, I couldn't convince myself to wear my maxis and midis with anything else. Even if I opt for fabrics like satin or silk, a pair of leggings and knee-highs can go a long way, I promise.

And while brands release a variety of skirts for the summer consisting of florals and bright colorways, it's the fall and winter styles that end up catching my eye. From ribbed and leather to pleats and velvet, the variety of the latter just ends up suiting my style a little bit more. Longer lengthen skirts also showed plenty on the 2021 runways with wrap skirts and knit pieces already taking center stage on the fashion scene. 

Ahead, you'll find 30 of the best long skirts I found that I'll gladly want to wear with a pair of boots right now in a range of fabrics, colors, and prints. There's something for everyone, trust me. 

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.