10 Incredibly Chic Ways to Master Summer-in-the-City Style

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As the winter chill sets in, we’re reaching for outfits that work overtime–warm enough for brisk subway commutes, not too bundled for the actual heat, still refined for martinis and steak frites after work. The right lineup of seasonal staples makes it possible to achieve this kind of goes-with-anything styling.

But where to start? The holy trinity of cold-weather must-haves–snuggly shearling toppers, cozy corduroy pants, and notable knitwear–lets you incorporate texture in a practical way. From there, it’s all about finding tension in your wardrobe by styling the basics alongside those personality-defining finds. Loafers and ballet flats can still be worn with socks, but all manner of boots, from little black ankle styles to knee-high stunners, anchor a city outfit with function and flair. (No slipping on icy cobblestones here!) Come nightfall, which always arrives sooner than you think, reach for elegant after-hours pairings that bring just the right amount of shine and sophistication–think off-the-shoulder tops with tailored trousers and colorful heeled sandals, lacy numbers with festive faux furs, and dazzling finishing touches to top it all off.

No matter the outfit, each of these individual pieces transitions seamlessly across your winter calendar, perfect for office days, cozy fireside cider dates, and nights out on the town. Below, shop nine looks to help you take on the season in true winter-in-the-city style.

Tailored Off-Duty

Model your next winter-in-the-city look after this effortlessly chic Paris Fashion Week attendee. Start with Frame’s shearling-lined leather aviator jacket and a pair of tailored navy trousers. Layer a classic blue button-up from Calvin Klein underneath for the perfect pop of color. Then let the accessories bring the look together: an embellished leather belt from Anderson’s, Mansur Gavriel’s caramel suede tote, and Khaite’s little black ankle boots complete the ensemble with understated sophistication.

Soft City Layers

Winter’s dressing motto? The more layers, the merrier. Start with Matteau’s checkered flannel shirt and Khaite’s dark-wash denim as your foundation, then add Calvin Klein’s beige trench and St. Agni’s cashmere crewneck for some very welcome extra coverage. The Row’s calf-hair mules keep things easy for everyday, while Alaïa’s suede tote is a sumptuous (and practical!) final touch.

Chic After-Dark

No seasonal hibernation here! Take your look downtown by pairing Proenza Schouler’s elegant off-the-shoulder top with Zara’s classic black trousers and a lined peacoat. Jimmy Choo’s red-hot heeled sandals deliver a true fashion-girl flourish, while Le Sundial’s tasselled handbag and Cartier’s stunningly simple Tank watch round out the look with refined ease.

Textured Winter Mix

Cold-weather dressing is nothing without a rich mix of textures—whether that’s a touch of shearling, a hint of lace, or croc-embellished shine. Luckily, this city outfit combines them all (and then some!). Wear this elite combination everywhere from your nine-to-five to date nights, and consider your winter blues instantly cured.

Boyish Charm

Sporty prep was one of fall’s defining dressing moods. Bring it into winter by channeling a bit of boyish charm in Adidas x Wales Bonner’s cherry-red zip-up, a pair of slouchy corduroy pants from Banana Republic, and Bally’s leather boat shoes. Banana Republic’s fabulous faux fur adds the high-fashion moment this look needs, while A.Emery’s classic leather tote gives it a discreet finish.

Knit Dressing Decoded

Winter’s answer to looking polished while feeling blissfully wrapped in comfort? A knitted dress–in cashmere, of course. This cable-knit number from J.Crew sets the tone, especially when styled with Toteme’s elegant calf-hair coat and slim-fitting ivory sock boots. Cozy up even more with Agnelle’s elbow-length leather gloves, then top things off with Khaite’s cord-pendant necklace and Bottega Veneta’s leather tote.

Winter’s Most Notable Neutral

We’re not here to wax poetic about leopard print. If you’re a regular Vogue Shopping reader, you already know how we feel about the pattern. All to say: we’re wild for Adam Lippes’ belted maxiskirt. Make it the centerpiece of your look by pairing it with Liberowe’s velvet lady jacket and Proenza Schouler’s stompy knee boots. Finish off with Reformation’s burgundy satin evening bag and a set of boho-inspired beads, courtesy of Jennifer Behr.

Everyday Cozy

Your weekend coffee runs just got a lot chicer, thanks to this next city outfit. Alex Mill’s V-neck argyle sweater and Levi’s low and loose blue jeans are style no-brainers, while Nour Hammour’s belted shearling coat takes the look to an entirely new level. For accessorizing, Nike’s LD-100 sneakers and Loewe’s newest black tote bag are easy add-ons, while a pair of emerald-cut drop earrings from Dorsey ties everything together with a subtle hit of shimmer.

Head-to-Toe Styling

Take a masterclass in head-to-toe styling with this final chic winter-in-the-city look. Start strong with Gigi Burris’s velvet pillbox hat, then layer on Rabanne’s cheetah-print cardigan, Tove’s clean-lined column skirt, and Alaïa’s two-toned suede boots. Leset’s plain white baby tee adds a soft underpinning, while Heaven Mayhem’s chunky silver cuff brings a sculptural finish.