There’s something about plaid that instantly makes an outfit feel expensive—and this winter, fashion insiders are swapping their jeans for long plaid skirts in every variation. Whether it’s a tailored wool maxi with pleats or a softer, brushed-cotton version that hits mid-calf, this classic pattern feels incredibly elevated when styled with seasonal staples like knee-high boots and cozy outerwear. The result is an outfit that manages to look both polished and effortless, no matter the occasion.
The modern way to wear the trend is all about balance. Try pairing a structured plaid maxi skirt with a slim turtleneck and sleek belt for a refined silhouette, or lean into a more relaxed vibe with an oversized knit tucked in just so. Either way, it’s a foolproof formula that instantly gives off “old-money” energy—a blend of heritage prep and modern minimalism that’s defining the winter aesthetic right now.
If you want to take the look a step further, look for longer lengths that skim the ankle. This elongated shape not only adds drama but also gives your outfit that runway-inspired, city-chic finish. Add a pair of tall leather boots (flat or heeled), and you’ll achieve that understated richness that’s everywhere from Paris street style to downtown Manhattan this season.
And while plaid skirts have always been a wardrobe mainstay, this year’s iterations feel particularly sophisticated. Think tonal tartans, subtle checks, and neutrals like camel, charcoal, and chocolate brown—all styled with luxe textures like cashmere and leather. It’s proof that you don’t need denim to look chic and pulled-together this winter—just the perfect plaid maxi.
See the chicest plaid maxi skirt outfits below and shop the non-denim pant trend along the way.
Get the look: Plaid maxi skirt + Plaid button-down shirt + Long coat + Kitten heels
Get the look: Plaid maxi skirt + Suede jacket + Brown sweater + Ballet flats
Get the look: Plaid maxi skirt + Crewneck sweater + Long necklace + Leather belt + Flats
Get the look: Plaid maxi skirt + Leather jacket + Tall leather boots + Suede gloves
Get the look: Plaid maxi skirt + Puffy bomber jacket + Tall socks + Sneakers
Get the look: Plaid maxi skirt + Oversized tan jacket + White t-shirt + Black boots
Get the look: Plaid maxi skirt + Brown jacket + Sweater+ Tall suede boots
Get the look: Plaid maxi skirt + Fancy black top + Black leather boots
Get the look: Plaid midi skirt + Fitted long-sleeve shirt + Headband + Sneakers
Get the look: Plaid maxi skirt + Black sweater + Fitted tall boots
Get the look: Plaid maxi skirt + Matching plaid jacket + Pointed-toe boots
Get the look: Plaid maxi skirt + Leather jacket + Black sweater + Loafers
Get the look: Plaid maxi skirt + Striped sweater + Oversized bag
Get the look: Plaid maxi skirt + Matching plaid top + Tall leather boots
Get the look: Plaid maxi skirt + Oversized wrap coat + Black riding boots
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