Sorry, Trousers—This Anti-Trend, Throw-On Dress Is My Go-To Wardrobe Staple This Winter
If there's one dress I'm forever a fan of, it's a black one. Knitted or silky, short or long, a black dress is a style I can always get behind—and that's coming from someone who typically steers away from dresses altogether. Part of their appeal is their versatility, and the fact that with a few clever accessory switches they can take you from day to night, casual weekend lunches to a much-anticipated date night. That being said, I'm always on the hunt for fresh outfit inspiration, especially now that I'm in winter outfit planning mode. Bring on the Instagram scrolling.
Let's start with the dress itself. In my opinion, nothing is more elegant than a long-sleeved midi or maxi dress, especially when its a finely knitted style. That's the kind of dress you could wear with a trench and trainers for a more casual ensemble, or with the very on-trend pointed-toe boots for a more seductive look. Then there are the evening wear options—slinky slip dresses, ankle-grazing maxis and sophisticated flowy styles will all score serious fashion points, and also can be styled for day by layering with cardigans or blazers.
If you're also looking for fresh black dress outfit inspiration, look no further—below I've found eight excellent black dress looks for every occasion, and every style.
7 BLACK DRESS OUTFITS I LOVE FOR WINTER 2024
1. Long-Sleeved Dress + Knee-High Boots
Style Notes: Knee-high boots are an winter staple, and these versatile shoes work particularly well with black dresses of all styles. Personally, I love the effortlessly elegant look of pairing sharp-toed boots with a demure long-sleeved dress. So classic.
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Woven leather is a trend I'm really loving at the moment.
A soft wool coat is the perfect winter outerwear.
2. Flowy Dress + Strappy Heels
Style Notes: With party season just around the corner, take advantage and incorporate some of your summer staples into your winter wardrobe by layering a warm coat over a flowy black dress and strappy heels.
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A tennis necklace is the required finishing touch.
3. Mini Dress + Long Coat + Flat Boots
Style Notes: Even if the temperatures plummet, you don't have to give up your love of mini dresses. Opt for a knitted style and pair with knee-high boots—these flat versions are particularly on trend this season—and an ankle-grazing coat to guard against sharp winds.
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4. Knitted Dress + Cropped Jacket + Pointed-Toe Slingbacks
Style Notes: All of us at Who What Wear are huge fans of knitted dresses, especially for transitional season dressing. Follow Abi's example and give yours extra definition by pairing with a cropped jacket that will accentuate the waist.
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If you don't want to give up on the mesh trend, these are the answer.
5. Slip Dress + Cardigan + Mary Janes
Style Notes: A black slip dress is a great piece to have on hand for evening wear, but Chrissy's look proves how easily you can style it for the day, too. A fitted cardigan adds some more shape, and the flat Mary Janes keep it relaxed yet polished.
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6. Maxi Dress + Metallic Boots
Style Notes: A black dress is a classic partywear piece for a reason. Ever since I saw this picture I've been dreaming of recreating the look—it just exudes such sophistication. The perfect balance of modern and classic style.
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Nothing screams 'party season' like a pair of metallic boots.
This is the kind of necklace you could wear with jeans and a t-shirt as well as an evening dress.
7. Mini Dress + Trainers + Trench
Style Notes: Is this the perfect winter weekend outfit? I think so. Lois expertly styles a black mini with a classic trench coat for a simple and polished look, before adding a trend-lead touch with colourful trainers and socks.
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Jess Kelham-Hohler is a freelance writer, editor and content strategist. She has been a contributor for Who What Wear UK since 2023. Currently based in London following six years in Washington D.C. and New York, she was previously the Digital Editor for Soho House & Co, an international group of private members’ clubs for creatives. She has interviewed a range of artists, creators and more, including Alighieri founder Rosh Mahtani, photographer Misan Harriman and fashion editor Lindsay Peoples Wagner. Today, she writes primarily about fashion, travel and culture for various publications, and has worked as a copywriter and content strategist for brands such as Belstaff, Olivela and Equinox.
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