How to Wear Long Skirts in Winter: 5 Style Tips

Friday, October 21, 2022
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The mornings turn crisper, the leaves turn redder, and the days turn shorter: fall and winter are upon us. If you’re anything like us, you’ve got it on your to-do list to start swapping out your trendy tops and shorts from summer, for heavy sweaters and sturdy boots. As the temperature drops and your closet transitions from warm weather clothing to pieces more suited for chilly weather, you’re probably wondering how to wear skirts in cold weather.

While they may not necessarily be a top contender on your winter clothes essentials list, you don’t have to pack your favorite skirts away just because you’re starting to be able to see your breath on your morning walks. Long skirts like maxi and midi skirts are some of our favorite winter wear staples. With so many ways to style a winter skirt outfit, keep reading for five tips on how to wear long skirts in winter.

#1 Try Tall Boots for Added Volume

Freshly harvested flowers, smoky squash pasta and crisp white wine, caramel-glazed popcorn and your favorite romantic comedy…some autumnal combinations that can only be described as pure magic.

And what’s one of fall’s most magic style combos? A long skirt and a pair of tall boots, such as knee high boots.

If you're wondering how to wear a long skirt in the winter season, when paired with a long skirt, tall boots create a striking and ultra-chic silhouette that’s perfect for a chilly fall and winter weather. Whether you’re hitting up the farmer’s market early or grabbing late-night tapas with your besties, here are our favorite ways to take these elegant long lines for a spin:

  • Use a solid-colored skirt to complement a show stopping set of boots. We love the sumptuous feel of our bias cut midi skirt in a rich, jewel-toned ruby red. To make a statement, wear it with a pair of tall white or black leather boots with a block heel. Or, opt for a slouchy suede boot with a slim heel for an effortless look.
  • Try out that ‘90s-inspired trend with a moody dark floral printed midi skirt—ideal for those dusky winter evenings). With a button-up front slit, it’s perfect for showing off a sky-high pair of black leather boots with a chunky heel. Tie the look together with your favorite chunky gold jewelry, throw on some Merlot-hued lipstick, and voilà: the perfect cold-weather outfit.

The best part about tall boots is the infinite versatility you’ll find them in: Not only will they keep your calves toasty and protected from the winter winds, but they’re undeniably fashion-forward and timelessly sleek.

Whether you’re drawn to a slouchy suede style, an eclectic cowboy boot, or an equestrian-inspired leather riding boot, tall boots are a fashion-forward way to make any long skirt in your closet wearable for winter.1

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#2 Keep Legs Cozy with Tights

While we love trendy dresses or midi and maxi skirts for winter, there are some days when even the longest hemlines aren’t quite enough to keep you warm. We also have a selection of petite and plus-size maxi skirts.

But you don't have to sacrifice your favorite long skirt outfit when the cold days come. If you’re wondering how to wear maxi skirts in the winter when the thermometer dips into the single digits (or even worse: below zero), tights are your winter wardrobe’s go-to secret weapon.

Fortunately for style enthusiasts, tights are far more than a practical cold-weather accessory. They’re an easy, cozy way to jazz up a long skirt we might have assumed we’d have to skip wearing on the chilliest of days.

To even the gauziest of long skirts suitable for winter wear, try introducing these 4 kinds of tights to your closet:

  • Opaque fleece-lined tights – From our perspective, these accessories deserve a starring role in your winter wardrobe for life. More than others, a pair of fleece-lined tights lend themselves to insulation so you can stay stylish and warm when you’ve decided to don a long skirt. For an ultra-luxe option, we love a soft textile such as cashmere or merino.

  • Semi-sheer black tights – Ever a classic, semi-sheer tights will keep your legs protected from harsh winds while also giving your winter skirt outfit a dark feminine touch. We recommend skipping these on the bitterest of winter days, but they’re still a go-to for styling with a boldly patterned long skirt, like this midi in a snakeskin print.

  • Patterned tights – Tights that sport eye-catching patterns are one of the most foolproof ways to add freshness when the winter doldrums hit.2 Try a black sheer tight with a checkerboard pattern for a mod look, or delicate Swiss dots for something more classic. If you’re looking for something really groovy, you can try tights in brights, florals, or swirling patterns.

  • Shimmery tights – Everyone deserves a glittering moment to light up their winter. Whether you don tights with metallic, tinsel-inspired threading or a bedazzled pair stitched with faux gemstones, seeking out a sparkly moment is perfect for holiday parties (or whenever you’re simply feeling festive). Let your shiny tights steal the spotlight by pairing a simple yet elegant skirt, like the Pull On Maxi Flare Skirt in black.

  • #3 Add Visual Interest with Prints

    When most of us think of a “winter wardrobe,” our minds may go to bulky sweaters, sensible snow boots, or our most colossal, closet space-stealing coat. But winter dressing certainly doesn’t have to feel boring—and long skirts are a gorgeous way to add a lighthearted touch when the weather outside is frightful.

    Printed long skirts in particular are just the thing to bring that carefree attitude. Some of our favorites include:

    • Marbled prints like our Tie-Dye Maxi Flare Hem Skirt. Pair it with a simple black or army green satin slip and an oversized faux-fur coat for a hip 70s-inspired take.
    • Desert-inspired prints like the Bias Cut Midi Skirt. This design reminds us of sandstone and Santa Fe, and we love it coupled with a flowing, sinuous top like the Drape Cami in soft satin.

    Printed long skirts have a knack for adding vibrancy to an otherwise neutral outfit. For busier patterns, like colorful stripes or bright paisleys, try mixing in a crisp, simple top or a solid silk blouse—it’s the essence of laid-back, just a few degrees elevated.

    #4 Layer in All-Seasons Favorites

    When it’s ultra-cold outside, few of us want to step out the door unless we’re fully bundled!

    Fortunately, knowing how to layer clothes for winter will be crucial to still being able to grab your long skirt of choice while adding texture and dimension to your outfit. To pull it off, combine your favorite all-seasons staples with fresh pieces that complement and contrast with your skirt’s length.

    Here are our favorite layering combinations to kickstart your cute cold weather outfits brainstorm:

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    #5 Embrace the Chill with Seasonal Accessories

    You’ve assembled your perfect winter outfit with your favorite long skirt as the centerpiece. Now, how to take it to the next level?

    Accessories provide a touch of polish to any look, elevate women's essential clothing pieces and put the finishing touches on your outfit. A wonderful rule of thumb is to select 2 to 3 key accessories to spotlight and complete your look.

    This winter season, these are our favorite ones to play up that midi or maxi skirt:

  • Belts – Belts let you play with the fit and drape of your skirt, as well as provide contrast between your top and bottoms. We love to pair belts with oversized buckles with cozy, chunky sweaters. For something sleeker, try pairing a slim leather belt with gold or silver hardware with a silk blouse—pulled together, polished, and effortless.

  • Shawls and scarves – Ideal for those months when you’re looking for as much coziness as you can get your hands on, swaddling up with shawls and scarves are gorgeous paired with long skirts. Try a sweater shawl to add some texture to a long maxi skirt, or bundle up with a pashmina for endless styling possibilities.

  • Felt hats – Give your beanie a break this winter and try leaning on a felt hat to tie your outfit together. These equestrian-chic pieces look charming paired with Western-inspired boots, some turquoise jewelry, and a moody, dark floral midi skirt.

  • Jewelry – Your favorite jewelry is a must for any season! When you’re donning a long skirt, try wearing jewelry that mirrors its length: think dangly earrings, long necklaces, and glittering pendants.

  • Bags – No bundled-up long skirt look is complete without the bag that’ll hold your winter essentials (no mittens lost here!). Try playing with texture and long visual lines by toting along a bag in natural textiles, like a cowhide tote or raffia tote bag. For extra complexity, complement your skirt’s length with a long macrame crossbody bag in creamy ivory.

  • Make Long Skirts A Winter Classic with Karen Kane

    Karen Kane designs are created to help you discover that spark of magic we feel when we find that perfect outfit—even when it isn’t the most magical season of the year.

    Propelled by our passion for protecting the planet and its inhabitants, our apparel, accessories, and jewels were made to make each woman feel beautiful and self-possessed in every season. Find your next favorite, sustainably-made outfit you’ll be wearing all winter long by browsing our collection of long skirts for women at Karen Kane today.


    1. Vogue. Katie Holmes Shows the Best Way to Wear Tall Boots.
    2. Byrdie. Make a Statement This Season in Patterned Tights.

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