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It may still be early in the season for your heaviest coats and chunkiest shoes, but that doesn’t mean you can’t start daydreaming about all the cute winter outfit ideas you’ll be putting together in just a few weeks’ time. Thankfully, there’s tons of street style inspiration doing the rounds right now (hi, Fashion Month). So you’ll find foolproof outfit combos to take note of if you’re looking to answer one of the biggest winter style conundrums: how to serve a lewk when it’s bitter cold outside.
A quick scroll through this article will show you how many of fall’s hero pieces are at work here (Chelsea boots! Shackets! Teddy bear coats!) meaning whatever’s on your wishlist right now—or already in your wardrobe—can be effortlessly layered and styled for the foreseeable future. Ahead, seven no-fail winter outfit ideas to help you painlessly master cold-weather dressing.
Shearling Coat + Printed Dress + Leather Boots
From the shearling jacket to the groovy print dress and leather boots, everything about this outfit is perfect for snowy or bluebird days. Best part? It’s also incredibly easy to copy with just three key pieces: a cozy coat, midi dress, and sturdy, weather-resistant boots.
AFRM Shailene Mesh Midi Dress
Ray Ban 58mm Aviator Sunglasses
Good American Pull On Boots
Wool Coat + Dad Hat + White Sneakers
Thick woolly coats may be a cold-weather mainstay, but they feel undeniably on-trend when styled with street-smart staples like crisp white sneakers and dad hats (ideal for keeping bedhead at bay). This timeless look allows you to move freely and quickly, whether you’re venturing out into the rain for a quick coffee run or leisurely browsing stalls at the flea market.
Cos Double Breasted Trench Coat
Cropped Puffer + Mini Skirt + Lug Sole Boots
Between the puffy coat, combat boot, mini skirt, and tiny bag, this look is all about contrast. The down jacket delivers instant warmth, while lug sole boots ground your ‘fit with a little chonk. Go bare-legged if cold temps don’t faze you (or if you’re hopping in and out of a car between destinations). Otherwise, slip into tights for a more sensible interpretation of how to wear to this outfit in the dead of winter.
Farm Rio Striped Puffer Jacket
Reformation Benson Silk Mini Skirt
Kate Spade Rubix Crossbody
Shearling Jacket + Blazer + Jeans
No need to burrito yourself in a massive down coat if you don’t want to. This shearling jacket and blazer combo is a total masterclass in layering—and super simple to recreate with similar pieces you likely already own (or plan to rebuy for fall). Complete the look by styling with pants or skirts in the same color family, or opt for your favorite pair of denim to offset the tonal vibes.
Mango Reversible Shearling Jacket
H&M Double-breasted Jacket
Levi’s Wedgie Icon Fit High Waist Straight-Leg Jeans
Quilted Jacket + Cargo Pants + Shades
Quilted jackets are nothing new for fall, but the baggy silhouette dominating the streets proves they can be a solid alternative to puffers this winter, thanks to the padded insulation and ample layering possibilities. The cool girl-approved way to style this piece is with equally roomy cargo pants, but you can easily swap the bottoms for leggings or sweats depending on your mood or plans. Chunky footwear provides a welcome height boost for splashing in puddles.
Madewell Corduroy Quilted Jacket
Outerknown Phoenix Puffer
BDG Blaine High-Waisted Skate Jean
Le Specs Rectangle Sunglasses
Shacket + Wide-leg Pants + Balaclava
Plaid shackets may be a cool-girl staple for fall, but they actually check many boxes for winter wear, too. Keep yours zipped up for max warmth—and to cleverly disguise any base layers you’re wearing underneath. (Hello, heat-tech bodysuit.) A knit balaclava, which we may or may not have to crown as *the* must-have accessory for winter, is the perfect finishing touch when temps don’t require you to wear all your cold-weather gear at once.
BP. Plaid Oversize Shirt Jacket
Leset Pointelle Drawstring Wide Leg Pants
3.1 Philip Lim Chunky Knit Balaclava
Duster Coat + Ribbed Set + Chelsea Boots
While the duster coat has captured the hearts of many A-listers for serving major main character energy with its dramatic, wafting silhouette, it’s also a seriously functional piece of outerwear for staying warm throughout the winter months. We love it paired with a matching set and weather-resistant boots for looking exceptionally polished while stomping on fallen acorns on a cool morning walk.