There are a lot of things to enjoy about getting dressed for winter. After all, is there anything quite as satisfying as slipping on a new cashmere jumper or pulling on your favourite pair of boots after an eight-month break? Still, that doesn’t mean dressing for the season doesn’t come without its challenges—especially where going out is concerned.
With diaries filled with everything from dinners with friends and trips to the theatre to low-key work drinks and maybe even some nights that call for serious glamour, assembling outfits to go out in for the colder months is nothing short of an art form. You need to consider your layering strategically, give some thought to your materials, and still work out a way to look cute in doing so. This might sound daunting, but there is a way to achieve the best of both worlds. In fact, I’ve found 11 ways.
For those who like to get dressed up, I’ve found several ways you can do so without the risk of frostbite. Then, there are those who refuse to part with their jeans. Don’t worry—I’ve got you, too. And if you’re anything like me and prefer to keep wrapped up like a toasty burrito, I’ve also pinpointed key looks that’ll allow you to keep your coat on and still look as if you’ve put a considerable amount of time and effort into curating your outfit.
Scroll on to see 11 popular going-out outfits to try this winter.
1. STRIPED JUMPER + SEQUIN SKIRT + HOOP EARRINGS
Style Notes: ’Tis the season for sparkle, but sequins aren’t exactly known for being warm. No problem. Style them with a chic jumper, and you’ll strike the perfect high-low going-out outfit balance.
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2. BUSTIER TOP + JEANS + LOGO BELT
Style Notes: I told you, you could keep your jeans on! Bustier tops are huge right now and look their coolest worn with loose-fit denim. (Oh, and a designer logo belt wouldn’t go amiss in the fashion stakes either.)
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3. CARDIGAN + SLIP DRESS + KNEE BOOTS
Style Notes: Satin and silk always look so beautiful, but again, what they give in aesthetics they lack in cosy practicality. Enter this stylish look from Aimee Song, who has expertly layered her rust slip dress with a matching cardigan. Isn’t the effect gorgeous?
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4. ROLL-NECK + LEATHER TROUSERS + FANCY FLATS
Style Notes: If you’re keen to change up your usual jeans outfits, look no further than a pair of leather trousers. Wear them with everything you’d ordinarily pair with denim. For winter going-out outfits, the addition of pretty flat shoes will go a long way.
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5. BLAZER + MATCHING TROUSERS + CAMISOLE
Style Notes: Suiting looks strong year-round, but it also makes for the ideal winter going-out outfit, as it provides more coverage than most dresses. Take your cues from Hannah of Cocobeautea and add a silky camisole for after-dark appeal.
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6. HEADBAND + SILK SHIRT + CLUTCH BAG
Style Notes: If in doubt, always keep your outfit simple and embellish it with statement, party-ready accessories. Ali Tate Cutler’s satin jacket provides a beautiful backdrop to her bow-adorned clutch and cute-as-anything headband.
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7. MAXI DRESS + CHUNKY BOOTS + SHOULDER BAG
Style Notes: Maxi dresses are one of my winter style BFFs, and clearly, Hannah Crosskey shares the same sentiment. The floor-grazing length feels instantly glam (even if you’re wearing it with opaque tights underneath). Finish with a pair of on-trend chunky boots, and you’ll be ready to go out, whatever the forecast may be.
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8. JUMPER DRESS + SHORTS + KNEE BOOTS
Style Notes: You’ve heard of wearing your blazer as a dress, but have you ever thought of wearing a jumper as a dress? Handily, Marks and Spencer has created a minidress very similar to Camille Charriere’s (sans feathers), which will look so stylish worn over tailored shorts.
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9. STATEMENT COAT + BLUE JEANS + MULES
Style Notes: Some outerwear is too special to be relegated to the coatroom. Instead, make a standout style the focus of your outfit, pairing it with straight-leg jeans and simple footwear. Thanks, Monikh Dale, for providing us with endless winter style inspo.
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10. LONG-SLEEVE DRESS + KNEE BOOTS
Style Notes: You needn’t forgo mini hemlines during the winter months, especially if you try Franny’s handy tip. Seek out long-sleeve dresses to ensure your top half is mostly covered, then offset with knee boots. Voila—a look that’s perfect for parties but that won’t leave you shivering.
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11. BLAZER + T-SHIRT + PARTY MINI
Style Notes: Blazers are a great addition to any winter going-out outfit, as evidenced by Hannah Lewis, whose oversized style will provide her some shielding from the elements without covering up her incredible Paco Rabanne skirt.
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