No Hate to Jeans, But If You Want to Look Chic This Winter, Wear This Exact Skirt Trend
Plaid has always had a choke hold on my fall-and-winter wardrobe—maybe it’s the British countryside romanticism of it all or simply the fact that the print just works when the temperatures drop. But this season, the plaid trend looks a little different. Instead of the micro minis or stiff pencil skirts we’ve seen in years past, the fashion world has fully pivoted to something far more wearable: the plaid maxi skirt. Picture long, full silhouettes in chocolate, camel, black, and tan, swishing around your boots and instantly making your outfit feel more considered.
Designers clearly got the memo, too. Fashion houses with real history in plaid brought the print back in a big way on their runways. And then there’s the viral COS plaid maxi skirt, which felt like every editor, influencer, and assistant hustling between shows during fashion month was wearing. The broader trend's appeal is obvious: clean lines, neutral tones, and a silhouette that feels elevated and relaxed without trying too hard.
Plaid Maxi Skirts on the Runway
COS fall/winter 2025
Ami Paris fall/winter 2025
Vautrait fall/winter 2025
After popping up on the runway, editors, influencers, and stylists alike began adopting the long plaid maxi-skirt look in their daily outfits and mirror selfies. While most of the runway looks may be paired with other print or statement tops, the majority of the fashion set's looks revolved around letting the plaid maxi skirt do all the talking—that is, pairing the trend with simple, understated key pieces like suede bombers and leather boots, for all-around chic look.
The preferred color combination for real-life plaid maxi skirt outfits is often darker, moodier, and more wearable than their runway counterparts, with the majority of looks leaning on chocolate, tan, white, and black hues.
What I love about this season’s plaid maxis is how easy they are to style. Pair one with a chunky knit, a suede bomber, or classic leather boots, and you instantly get that effortless countryside-meets-city vibe. Trust me—if you’re looking to look chic this winter with absolute minimal effort, this is the skirt trend to reach for.
Plaid Maxi Skirts on the Fashion Set
How to style: Oversize twill bomber, plaid maxi skirt, and black boots
How to style: leather jacket, plaid maxi skirt, and brown boots
How to style: Wool coat plaid maxi skirt, plaid button-down, and black sandals
How to style: Suede jacket, plaid maxi skirt, chunky knit, and black ballet flats
Shop Plaid Maxi Skirts

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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