20 Chic Ways to Style a Long Skirt for Winter

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Long skirts have made a comeback in a range of styles from boho to denim to slinky silk. Celebs like Katie Holmes and Hailey Beiber have been spotted in the full-length look, and the trend doesn’t appear to be going away any time soon. The long skirt can be a versatile piece in any wardrobe, and it can be styled casually for a relaxed weekend outfit, or dressed up more formally for the office or a special occasion.

An outfit centered around a full-length skirt can be the perfect mix of fashionable and comfortable—there’s extra coverage and plenty of loose, flowy pieces to choose from—but the styling might feel a little tricky if it’s not a proportion you’re used to wearing. We’ve rounded up 20 outfit ideas spotted on street style stars.

01 of 20

Pleated with a Blouse

Long Skirt- pleated with blouse

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If you’re not the boho type, a pleated long skirt is a more polished, office-ready style. Paired with a sculptural blouse and a simple black leather crossbody bag, this outfit looks professionally cool.

02 of 20

With a Cropped Top and Leather Jacket

Long Skirt- Crop Top and Leather Jacket

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Long skirts might conjure up images of old-fashioned, prim styles, but Elsa Hosk proves the look can be edgy and cool. Her khaki maxi could have been styled more conservatively, but the addition of a cropped turtleneck and a black leather jacket made it much more bold.

03 of 20

Silk and Neon

Long Skirt- Silk and Neon

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A silky long skirt is a sexy and seasonless wardrobe staple—it can be dressed up or dressed down, styled simply, or layered with sweaters and boots for warmth and interest. We love it here with a sleek neon top and sparkly bag for a party-friendly outfit.

04 of 20

With a Sweater Vest

Long Skirt- Sweater vest

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Another classic wardrobe piece having a moment this year? The sweater vest—and it pairs perfectly with a long skirt. With the pumps, belt, and twisted chignon, this is an outfit just beginning to stand out at a big meeting.

05 of 20

Slouchy Knit Set

Long Skirt- Slouchy Knit set

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For a cozier, more relaxed long skirt outfit, try a set of coordinating knits: a maxi and an oversized sweater. Nothing could be warmer or cuter for a winter weekend.

06 of 20

Animal Print and Sneakers

Long Skirt-Animal Print and Sneakers

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When we say maxi skirts can be styled any way, dressed up or dressed down, this is what we mean: a polished, voluminous skirt, paired with dad sneakers and a playful zebra stripe tee? It shouldn’t make sense, and yet it works perfectly.

07 of 20

Plaid Jacket and Crop Top

Long Skirt- Plaid jacket and crop top

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This is not your grandfather’s three-piece suit! A modern twist on that classic, this is a much more fun way to wear a trio of coordinated pieces—or you could swap the cropped top for a white tee for a slightly more subdued look.

08 of 20

All-White

Long Skirt- All White

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Wearing head-to-toe white with a maxi skirt and coordinating button-down blouse is a crisp and elegant way to wear the trend. The slight crop of the top and the chunky leather boots keep this look balanced.

09 of 20

Boho Florals

Long Skirt- Boho Floral

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If you prefer a romantic vibe for your long skirt, might we suggest a matching set of florals? This is such a sweet way to wear this trend.

10 of 20

Denim on Denim

Long Skirt- Denim on Denim

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The once-maligned Canadian tuxedo has been a fashion staple for years now, and swapping the jeans for a long denim skirt just makes it even better.

11 of 20

Pattern Mixing

Long Skirt- pattern mixing

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A bold floral maxi skirt is already a statement piece, but it can handle another major outfit element like this full-length plaid coat for a complete look. The key here is keeping the very different patterns in the same color family.

12 of 20

Draped Gray

Long Skirt- Draped Gray

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Groutfits—all gray outfits—emerged as an alternative to Barbiecore and a “quiet luxury” subdued hue. And the monochromatic look is perfect for a winter-friendly long skirt outfit with a wrapped skirt belted over a gray turtleneck and blouse.

13 of 20

Stripes

Long Skirt- Stripes

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French girl chic, anyone? A classic striped top is a match made in Parisian heaven with a maxi and a pair of of-the-moment ballet flats.

14 of 20

Laidback Layers

Long Skirt- Laidback Layers

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How great does this ornately patterned velvet maxi look with this layered gray T-shirt? Such a great way to make a more formal skirt work for the daytime.

15 of 20

With a Slouchy Sweater

Long Skirt- Slouchy sweater

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Your flowy, summery maxi skirts can absolutely be styled for colder weather too—just throw on a chunky knit and you’ve got a laid-back look that won’t leave you chilly.

16 of 20

With a Tie

Long Skirt- with tie

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When menswear meets a maxi, it’s a major fashion moment.

17 of 20

Turtleneck Sweater

Long Skirt- Turtleneck sweater

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What’s black and white and perfect for practically any occasion from work to a holiday dinner party to meeting your new boyfriend’s family? This classic long skirt outfit.

18 of 20

With a Blazer

Long Skirt- with blazer

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Here’s a more exaggerated version of that dainty skirt-polished jacket combo: a wispy pastel maxi topped with a formal plaid blazer. The sneakers add another unexpected element.

19 of 20

Ruffles and Bold Color

Long Skirt- Ruffles and bold

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While we’ve seen that long skirts can work in heavier fabrics like wool or denim, a floaty, ruffly, chiffon maxi is a lighter and more romantic option. We love the bold burnt orange here, especially when paired with a similarly toned jacket that adds a little structure.

20 of 20

With Silver Boots

Long Skirt- With silver boots

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We’ve seen that boots, heels, and sneakers can all work equally well with a long skirt, but this is an unexpected shoe choice that’s a great addition to the mix: a silver cowboy boot that adds a little dazzle to an otherwise simple striped skirt and blazer.

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