How to Wear a Sweater Over a Dress, No Matter the Occasion

Woman wearing red sweater over silk slip dress on beach


Winter is trudging on at a glacial pace. We’ve reached the frigid, dreary point of the season when we simultaneously want to stay cozy with a sweater every single day, but have also had it up to here with stifling, pant-centric cold-weather outfits. We don't know about you, but we’re ready to defrost: to escape our winter woes and slip into dresses again.

If you're looking to bring dresses into your cozy, knitwear-centric winter wardrobe, the solution is to wear both. By styling this somewhat unlikely pairing with the carefree, saltwater-hair spirit of warm weather while still addressing practicality, you have a winning combo on your hands.

Ready to throw a sweater on over your favorite dress, but not quite sure how to bring it all together? Ahead, see nine outfit formulas—and a few styling tricks on exactly how to wear a sweater over a dress—that will serve you well during countless occasions to come. We can’t banish winter, but these ensembles will inject the final gusts of the cold-weather doldrums with rays of sun-kissed style.

For Work: Prep's cool

This combination is made for work: It’s a great way to wear your favorite dresses to the office without looking too done-up, to protect yourself from the finicky blasts of AC and heat, and to display a playful melding of prep, professionalism, and layering expertise.

To create the ultimate preppy vibes, wear a pleated dress underneath a sweater vest. Add a crisp white button-down in between the layers if your dress of choice is sleeveless. Finish the look with a blazer, tights, a commanding but refined bracelet, and a pair of knee-high leather boots or polished loafers

For Whenever: Contrasting shapes

An oversized cashmere bell sleeve sweater and black mini shift dress are comfortable enough to wear all day and chic enough to take you from morning coffee to happy hour. Accessorize with a roomy bag and some simple Mary Janes that you can dash around in. You can even layer this look further with a pair of well-tailored trousers. Note that flipping the bottom of a sweater and tucking it in will create a shorter, more interesting silhouette, also eliminating floppiness.

For Date Night: '90s minimalism

Sleek, minimalist '90s style is perhaps the ultimate cold weather date night outfit inspo. When done well, wearing a sweater over a dress is sexy but mysterious and, perhaps most importantly, a cool look–so you'll feel comfortable and confident. You can't go wrong by pairing a slinky, low-cut slip mini or midi dress with a simple cardigan, which you can button from the top or bottom. Seal the deal with a long necklace, a pair of strappy metallic heels, and a clutch or evening bag.

For Cocktails: Texture play

When you’re meeting friends for a well deserved cocktail or mocktail, play with unexpected fabric pairings to match the fun evening vibes. Go for a textural midi dress and a cashmere V-neck, and skyrocket the look to space with a vibrant, futuristic bag. Turn up the contrast with lug sole ankle boots.

For Running Errands: Sports star

Keep things casual and comfortable for a day of running around in a mini denim or cotton polo dress and a cashmere duster, cinched with a belt. Slip into a pair of ballet flats and carry a roomy, functional tote.

For Events: Give them the warm shoulder

Going to the opera, a semi-formal party, or a rehearsal dinner? A bold, long dress is the nucleus of this ensemble, and a bolero cardigan makes it winter-appropriate as a fresh alternative to a formal jacket or wrap. Complete the look with heels, a miniscule fan bag, and elongated earrings.

For Hibernating at Home: Warm and fuzzy

Luring yourself out of pajamas and getting dressed may feel daunting at times, but it takes mere minutes and is guaranteed to make you feel more confident, put together, and productive. We’re pretty hardcore about only wearing loungewear while at home, but why not elevate it ever-so-slightly?

When you make it out of bed, put on a sleek, super-soft dress, a pair of ornate slippers, and, of course, a fluffy, dreamy sweater or knit hoodie, which will serve as a stand-in for your duvet. Style your hair with a luxurious scrunchie or headband, and you have an instant confidence boost that's cozy enough for lounging around but dressed enough for bodega runs.

For Travel and Staycations: Pot of gold

Going on a much-needed vacation or taking a staycation? Pair a bright yellow, mango, or gold-toned dress with a coordinating sunny turtleneck, detailed with a subtle chain or braided belt. Note that a slim-fitting sweater can also be worn under a dress, so your styling options are infinite.

For Gallery-Going: Show your stripes

If you're headed out to do something artsy, create a playful orchestra of clean lines with a striped dress and cardigan. Keep the rest of the look simple with a pair of ballet flats or patent loafers and an understated vanilla bag.

Related Stories