40 Stellar Street-Style Outfits to Try This Winter
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Getting dressed in the winter can be a blast — boots, scarves and adorable head-warming hats are our favorite accessories, after all. But on the flip side, coming up with endless chic winter outfits can also be an extremely exhausting task. We all get what we like to call “dresser’s block” (yes, that’s the equivalent of writer’s block) during the cold months.
Getting stumped when it come to building the perfect outfit often has less to do with not having the right items, and more to do with knowing how to put them together. We all probably own staples like a sleeveless dress and a black turtleneck, but we all might not think to pair them up. In fact, it’s a safe bet that we all have stuff sitting in our closets right this second that can be worn in dozens of unexpectedly stylish ways — all we’re missing is a small dose of inspiration.
To help you (and us) out, we combed through tons of sites filled with street style eye candy (hello, Pinterest!) to bring you 50 fabulous winter-ready outfits to copy right now. These looks might not seem groundbreaking, but they’re not meant to be — they’re just extremely thoughtful, cool, clever examples of how to put pieces together to create outfits that are both impactful and stylish by using things you might already have in the depths of your closet. We’ve also noted why the outfits work, and included small styling tips to help you achieve maximum levels of chic.
Go ahead and click through! We guarantee the street style photographers will be snapping you in no time.
Leather leggings and denim
Such a cool look—and so easy to recreate. All it takes is a pair of leather (or faux) leggings, a denim shirt and your favorite sweater. From there, pile on the bracelets, grab your favorite structured bag and top it off with a cool fur coat. Perfect daytime outfit!
Image via Lolobu
A statement stole
Break up a monochromatic, all-black look with a green fur stole—faux or real, the choice is yours—for a cool, cozy ensemble.
Photo: The Haute Pursuit
Cozy cardigan
Toss a slouchy, oversized Fair Isle cardigan over a printed blouse and colored jeans for a cozy-cool outfit, and pile on plenty of arm candy.
Image via Song of Style
Accessorize for success
All about the accessories! A leather clutch and cool shades elevate this relatively ordinary outfit of a plain black sweatshirt and super-distressed jeans.
Image via They All Hate Us
Neons and basics
A neon fuzzy sweater looks so chic with a pair of distressed jeans and gem-encrusted statement earrings.
Image via The Glitter Guide
Denim on denim
Double denim + statement coat = so chic (and so easy!)
Image via Caroline's Mode
Shorts and tights
Don't store those denim cutoffs! Wear 'em all winter long with thick tights, blouses and sweaters.
Image via Adam Katz Sinding/Le 21ème
Bright fur
Seek out a brightly-colored fur collar to liven up a basic winter look.
Image via Tory Burch
Keep it simple with neutrals
Quirky accents
A quirky sweater can totally make an outfit. Points for this gals' idea to mix bright red with burgundy.
Image via Atlantic-Pacific
Sweats to the rescue
Layering a gray sweatshirt over a ladylike dress feels so fresh and modern.
Image via Caroline's Mode
Duck boots
A master class in how to make duck boots look stylish. A perfect snowy-day look for gals at a loss when it cone to looking cute in inclement weather.
Image via Classy Girls Wear Pearls
Cinch a puffer vest
So clever: Using a skinny belt to cinch a sporty puffer vest.
Image via Harper's Bazaar
All about the details
Two methodical slits at the knees of skinny blue jeans makes the whole outfit extra-modern.
Image via Marion WD
Layers on layers
Try layering two button-down shirts (one printed or plaid, and one solid or denim) and rolling up the sleeves to show off the cuffs. So smart.
Image via Atlantic-Pacific
A classic ensemble
Cropped pants and oxfords look extra-cool when paired with a slightly oversized coat, leopard blouse and boxy bag.
Image via Pinterest
Cropped trousers and booties
An easy trick to copy: Add black socks to cropped trousers and ankle booties. Then add a chunky turtleneck sweater and an oversized peacoat.
Image via Emerson Fry
The little details count
Small details like gray sleeves peeking out from a coat's sleeve give outfits that extra something. Plus, an oversized pouch makes a great day bag.
Image via Pinterest
Bright on black
Try a bright-colored beanie with an all-black outfit.
Image via Le Fashion
Shift dress
Layer a black turtleneck under a sleeveless shift dress.
Image via Pinterest
Baseball caps
Don't reserve your baseball caps for Saturday morning coffee runs! Look how cool this one looks with a gray sweatshirt, fancy coat and leather clutch.
Image via Refinery 29
Unexpected combos
Unexpected in the best way possible: A sleek pair of heels with a chunky fair isle sweater and cuffed blue jeans.
Image via Elle.com
Shorts instead of a skirt
Replace a skirt with loose loose leather shorts for a modern approach.
Image via T-heatrical
Cords for days
Seek out a pair of super-flared corduroys.
Image via Pinterest
Sandals, yes, sandals
Break out a pair of evening sandals in broad daylight! The trick? Pair them with cool socks and an outfit comprised of basics.
Image via Elle.com
Skinny belts
Use a skinny belt to cinch an oversized sweater.
Image via Pinterest
Layering fur
On mild days, layer a fur vest over a leather motorcycle jacket. (Tip: This also works over army jackets, denim jackets or overcoats).
Image via Pinterest
Snoods
Try a fur snood instead of a scarf.
Photo via Am Lul
Sparkles
A fabulous way to dress down a sequin tank: Layer it under a cardigan and a jacket, and add cozy winter accessories and broken-in jeans.
Image via From Ainsley with Love
Pop your collar
We love the idea of layering a buttoned-up denim jacket under your overcoat. Pop the collar for extra style points!
Image via Caroline's Mode
Metallics with basics
Pair a dressy metallic maxi with a white T-shirt and leather moto jacket. Too ambitious for daytime? Try this look ultra-cool look for a night on the town.
Image via Pinterest
Slouchy socks
Try slouching a thick pair of socks over super-skinny jeans and finishing off the look with a cool pair of ankle boots.
Image via Bldg 25
Say "yes" to white after Labor Day
A perfect example of how to winterize white jeans.
Photo via StyleSaint
Oversized sweaters
Wear an oversized sweater as a dress! Just add tights and boots.
Image via Fashforfashion
Day time cocktails dresses
A cocktail dress worn over leggings with flat boots? Genius!
Image via Caroline's Mode
White on white
A stylish, thoughtful way to wear all white post-summer. Throw on a black overcoat and you're done.
Image via Harper's Bazaar
Fashion forward sneakers
Proof that sneakers can look beyond stylish.
Image via Tumblr
