7 Dress and Skirt Styles that Look Amazing with a Sweater

Celebrating sweater weather often involves pairing your favorite sweaters with your go-to jeans, leggings, and dress pants. That’s an injustice to sweaters which can dress up any outfit with ease. Expand your horizons and step out of your fashion comfort zone with these seven unexpected – but super cute – ways to wear your favorite sweaters. Your wardrobe has more potential than you realize! From minis and long cardigans to marvelous metallic pieces, we’re here to help you explore the style possibilities with the sweaters in your closet.

1. Mad for Plaid Skirts and Sweaters

Ash Grey Sweater with Back Bows, $62

Plaid skirts and sweaters are a can’t-miss combo. Opt for a mini style in blackwatch plaid or a lovely tartan, and pick sweaters in neutral colors, such as a grey sweater or hunter green, to match. If you have an understated sense of fashion, then black and white check is a sophisticated pick that matches with pretty much anything from a bright cherry-red sweater to elegant jewelry. For a flavoring of punk rock style, check out short, pleated skirts with straps and buckles. Throw on thick tights or knee socks and chunky slip-on platforms, or go a different route and wear combat boots. 

Ready to fully embrace fall-fashion and get away from mini styles? Opt for longer plaid skirts like midi skirts that help you to put together a retro-inspired ensemble. With high-waist skirts, you can wear a shorter sweater including crop top styles. Pullovers work, too, regardless of the length of your skirt. 

2. Two-Piece Glam

Grady Metallic Coated Cable Sweater, $495

Creating skirt and sweater combos for casual cocktail parties and semi-formal occasions is effortless – all you need is a little glitter. Keep your eye out for metallic skirts to pair with your sweaters. A short silver skirt is the ideal base for a fun party outfit, or think about a fitted gold midi skirt for a lighthearted evening event, such as a girls’ night out or New Year’s Eve. Step out in a long, sweeping bronze skirt paired with an elegant gold watch to add a touch of glamour to your day-to-day.

To keep the glitz going, shop for a matching metallic sweater! Metallics are in, so it won’t be hard to spot a silvery sequin sweater or a crop that glimmers with gold threads. Here’s a style tip that will never steer you wrong: tuck your sweater into your skirt and accentuate your outfit with a complementary or contrasting belt. Either wear a matching metallic belt or try a bold black piece that draws attention to your waist.

3. A Jazzed-Up Jumper

Cat Scratch Skirttail, $58

Don’t sleep on the appeal of dresses and sweaters matched together! There are several dress styles that are designed to pair with sweaters, like on-trend jumpers. The cutest jumpers beg for a sweater to go underneath. Show off some skin and pair your jumper with a cropped sweater, or tuck in a long sweater and throw on a flowing kimono cardigan sweater to keep warm and cozy.

4. Combining Cropped Sweaters and Midi Skirts

Morais Ruched Sleeve Sweater Crop Top, $55

On the subject of cropped sweaters, they look phenomenal with skirts! Forget about your high-waist jeans and trousers. Give off a Boho-vibe in a printed skirt and a sweater with long, full sleeves that fall past your palms. Piece together an alternative to a standard cocktail outfit with a black midi or maxi and a matching sweater. Add a pair of black pumps or high heeled black booties, and you’ve got yourself the perfect vampy ensemble.

5. Short Skirts and Long Sweaters

You’re My Darling Black Tweed Sweater, $52

The reverse is a stylish combination, too. Oversize sweaters are cute, cozy accompaniments to shorter skirts.

“A longer, oversized sweater over a form-fitting mini makes an undeniably stylish style juxtaposition,” said Tori Gerbig, CEO of Pink Lily Boutique. “The contrast between a too-big sweater with a structured, formal skirt is the perfect way to create a laid-back chic look without trying too hard – perfect for those cold fall mornings where getting out of bed to get ready is hard!”  

To keep it casual, consider a corduroy skirt with a ribbed sweater or pairing your plaid mini with a roomy navy sweater. For dressier occasions, choose a sequined or embroidered skirt with a ribbed, knit sweater.

6. Dresses and Duster Cardigans for Drama

Duster Cardigan, $80

Duster cardigans are dramatic and in-demand this season. There’s something edgy and a bit exotic about a cardigan that falls to the floor. A basic solid color can anchor your outfit, especially if it’s black or navy, or you can experiment with bold pattern mixing for an eye-catching look. A duster with large stripes pairs perfectly with a floral dress, for example! Play around with dresses of different lengths, as well. Step out in a long cardigan, a short skater dress, and cowboy boots. A fitted maxi dress layered beneath a duster can give off bewitching, mystical vibes.

7. Impress in a Sweater Dress

Knit Cowl-neck Dress, $50

Dresses and sweaters belong together, but why not cut out the middle man? Give in to one of the hottest trends and slip into a stylish sweater dress. You get the best of both worlds, not to mention a versatile piece of clothing!

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A one-and-done outfit saves time without forcing you to sacrifice your sense of style. Head to the office in a smartly patterned sweater dress and blazer. For running errands, throw on a long maxi style for a cozy winter-time look. If all else fails, you can’t beat a sweater dress and a festive pair of tights.

Don’t discount the effect of wearing a sweater over your favorite dress, either. For example, you can wear a trendy virgin killer sweater on top of your dress.

“Sweaters with dresses give you the opportunity to get creative with your wardrobe choices,” said Rachel Kelly of Saved by the Dress. “Put-together, chic street-style means working with what you have in your closet. If you have a maxi dress that you love in the summer, move it into your winter wardrobe and pair your fair chunky sweater overtop. It creates an unexpected – yet super stylish – way to combine your seasonal wardrobes!”

How do you wear your sweaters? What’s your favorite outfit? Tweet us @litdarling.

About the Author
Tess DiNapoli is an artist, freelance writer, and content strategist. She has a passion for yoga and often writes about health and wellness, but also enjoys covering the fashion industry and the world of fitness.

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