Revive Your Winter Wardrobe With These Maxi Skirt & Boot Combinations

Possibly the chicest thing you can wear in cold weather.

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Instagram / Marianna Hewitt
maxi skirt with boots outfits
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I take curating my yearly recap post on Instagram very seriously. Every January like clockwork, I peruse my camera roll and reminisce on some of my best OOTDs from the past 12 months. This time around, after narrowing my draft down to a select top ten, I realized that one wintery outfit formula was reigning supreme: maxi skirts with boots. The photos don’t lie — I styled the timeless combo over 15 different times in 2023, and not to toot my own horn, but each final ‘fit adapted to the chilly temps while still serving a lewk. All this to say? To no one’s surprise, the easy pairing already has a starring role in my 2024 wardrobe. To add it to yours, too, I suggest taking style cues from this season’s fashion week attendees who are wearing the pieces together in inspiring new ways.

Only a few days into the current Fall/Winter 2024/2025 fashion show circuit, maxi skirts paired with boots have began to flood the crowd outside the shows. Kicking off the menswear Milan Fashion Week festivities on Jan. 12, a guest was photographed in a high-low denim skirt and black ankle boots featuring a subtle platform. While their choice of footwear was certainly an on-point choice for the chilly forecast, the insider leaned even further into the wintery vibes by layering a mustard yellow Miu Miu puffer jacket overtop a burgundy sweater. Just a few days later in Paris, the combination was spotted again on Maria Bernad, designer and founder of LES FLEURS. Dressed in a reflective royal blue wrap skirt and Givenchy’s of-the-moment Shark Lock boots, the mix was the perfect match for her cropped black puffer.

A guest at Milan Fashion Week in January 2024.Edward Berthelot/Getty Images Entertainment
Maria Bernad at Paris Fashion Week in January 2024.Christian Vierig/Getty Images Entertainment

Chances are, you can expect to see plenty more maxis and boots both on and off the runways once womenswear collections debut this coming February. Get ahead of the game here, where I’ve gathered five right-now ways to mix-and-match these staples.

Film Noir

Spice up the tried-and-true all-black look by experimenting with different shapes and motifs. For instance: a pinstripe pencil skirt adds subtle dimension to your overall look, while patent leather knee-highs create a sleek finish. Up the ante with a noir stealth wealth coat and a coordinating croc-embossed bag. Extra points if you pop on red lipstick.

Girly Grunge

Watch out snow boots — Dr. Martens are coming for your crown. The iconic lace-ups are just as durable as your favorite waterproof all-weather alternatives thanks to their chunky, durable soles (the effortlessly cool factor is a bonus). They also happen to look ten out of ten amazing with a dark denim maxi skirt. Play up the moody vibes by adding in a dark cashmere sweater and slightly distressed leather jacket; an oversized handmade tote will add a sense of fun.

Western Flair

Over the summer, white flowy poplin maxis became a free-spirited essential for a certain subset of fashion girls. And while you might’ve packed yours up once the temps first dropped, I implore you to take that baby out a bit ahead of schedule. Winter-ify the summery piece with a matching baggy turtleneck and then opt for colorful cowboy boots (I highly suggest Miron Crosby) as well as opal hoop earrings.

Buttery Smooth

Layered-up looks are inevitable in the chillier season, but with the right blend of textures, your stacked selections won’t feel bulky at all. Start with patent boots to add a hint of shine to the overall outfit, then layer a matte leather skirt overtop for some contrast (a chocolate brown suede shirt helps with that as well). While Summer Fridays co-founder Marianna Hewitt opted for black shoes here, brown boots will work wonderfully, too — especially if you want an element of visual surprise.

Red Redux

No matter the season, beige on beige is a foolproof pairing that works with pretty much any shade on top, be it another chic neutral or fiery crimson. Should you opt for the latter hue, though, keep your silhouettes simple, allowing the striking clash of colors to take centerstage.

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