Work Style

Get Inspired by These Outfits with Skirts This Winter

by Caroline Grace


Every woman should have a variety of skirts in her closet. Not only are these garments charming and feminine, but their versatility can go such a long way for creating different looks. After your friends—and Instagram followers—have seen you wear a skirt once, how can you get creative and keep your look fresh? Whether you’re heading to your desk or to drinks, here’s some inspiration on how to put together outfits with skirts and make the most of these wardrobe essentials.

Keep It Crisp for the Office

A crisp white shirt is your secret weapon when wearing any skirt to work. Whether you’re wearing a skirt that’s striped, floral-printed, or covered in gold brocade, a white blouse will neutralize any party vibes and make the outfit immediately feel like workwear.

Miniskirts might seem like the most challenging skirt style to take from the bar to the boardroom, but they can be transformed with tights and a pointed-toe ankle boot. Midlength skirts are perhaps the most versatile for the office—just add a smart pair of pumps, and everyone in your pitch meeting will remember your ensemble for the right reasons.

Woman in office attire

Dress It Down for the Weekend

A thick, oversize sweater and heeled, round-toe ankle boots will turn even the dressiest of skirts into a more casual look for off-duty days. Embellished skirts, metallic fabrics, and rich printed styles, which are traditionally dressy, can also be toned down with this combo.

When it comes to length, short or midlength skirts are especially versatile for casual occasions, and even a polished pencil skirt will look dressed down when worn with semi-sheer black tights and those round-toe ankle boots. If you’re trying to make a full, flared skirt work for a Saturday, pair it with a pullover and a pair of knee-high suede boots to offer more casual textures in a way that works with that fuller silhouette.

Go Feminine for Date Night

A skirt is the perfect feminine garment for any date night. If you’re showing off your legs with a miniskirt, knee-high black suede boots and sheer black tights will complement the high hemline. If you’re going with a printed skirt, opt for glossy patent leather heels in a color that’s featured in the print to tie everything together. To finish off your look, add a neat neutral sweater or a button-front cardigan—and maybe a cocktail.

Get Fancy for Parties

Pairing a skirt with a metallic blouse or jewel-encrusted occasion heels will always make you feel ready to party. Longer or fuller skirts will make a statement as you enter a room, while the curve-hugging silhouette of a pencil skirt is ideal for cocktail parties and swanky bars.

When picking out a skirt, think about which party top will balance out your look. A slim-fitting knit top, perhaps in a Lurex fabric, will complement a more voluminous skirt, while a looser chiffon blouse will work well with a pencil skirt. Tops with balloon or flare sleeves will look great with figure-hugging skirts, while clingier tops look best with skirts with flare. Try on a few variations and experiment with your silhouette formula before you head out the door.

Outfits with skirts are perfect for working hard at the office or catching up with friends on the weekend. A good skirt can serve as the centerpiece of your look, and this can’t-go-wrong wardrobe essential can be dressed up or dressed down and worn so many different ways. Pull your favorite skirt out of the back of your closet, or put one in your shopping cart, and then have fun styling it this winter with these ideas.

Woman wearing a floral skirt

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