40 Stellar Street-Style Outfits to Try This Winter

Perrie Samotin
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40 Stellar Street-Style Outfits to Try This Winter
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Photo: Getty Images

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.

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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.

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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.

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Leather leggings and denim
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
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
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
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
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
Denim on denim

Double denim + statement coat = so chic (and so easy!)
Image via Caroline's Mode 

Tartan prints
Tartan prints

Time to revisit your classic plaid scarf.
Image via Clutter & Chaos 

Shorts and tights
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
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
Keep it simple with neutrals

Khakis done right.
Image via The White Pepper

Quirky accents
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
Sweats to the rescue

Layering a gray sweatshirt over a ladylike dress feels so fresh and modern.
Image via Caroline's Mode

Duck boots
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
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
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
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 

Red boots
Red boots

Red booties totally transform an otherwise basic outfit.
Photo via Courtney Approved 

A classic ensemble
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
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
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
Bright on black

Try a bright-colored beanie with an all-black outfit.
Image via Le Fashion

Shift dress
Shift dress

Layer a black turtleneck under a sleeveless shift dress.
Image via Pinterest

Baseball caps
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 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
Shorts instead of a skirt

Replace a skirt with loose loose leather shorts for a modern approach.
Image via T-heatrical 

Tights and peep-toes
Tights and peep-toes

Try pairing peep-toe sandals paired with thick tights.
Image via Refinery Magazine

Cords for days
Cords for days

Seek out a pair of super-flared corduroys.
Image via Pinterest

Sandals, yes, sandals
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
Skinny belts

Use a skinny belt to cinch an oversized sweater.
Image via Pinterest

Layering fur
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
Snoods

Try a fur snood instead of a scarf.
Photo via Am Lul

Sparkles
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
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
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
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
Say "yes" to white after Labor Day

A perfect example of how to winterize white jeans.
Photo via StyleSaint 

Oversized sweaters
Oversized sweaters

Wear an oversized sweater as a dress! Just add tights and boots.
Image via Fashforfashion 

Day time cocktails dresses
Day time cocktails dresses

A cocktail dress worn over leggings with flat boots? Genius!
Image via Caroline's Mode 

White on white
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
Fashion forward sneakers

Proof that sneakers can look beyond stylish.
Image via Tumblr 

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50 Perfect Outfits to Copy This Winter

50 Perfect Outfits to Copy
This Winter
  • Leather leggings and denim
  • A statement stole
  • Cozy cardigan
  • Accessorize for success
  • Neons and basics
  • Denim on denim
  • Tartan prints
  • Shorts and tights
  • Bright fur
  • Keep it simple with neutrals
  • Quirky accents
  • Sweats to the rescue
  • Duck boots
  • Cinch a puffer vest
  • All about the details
  • Layers on layers
  • Red boots
  • A classic ensemble
  • Cropped trousers and booties
  • The little details count
  • Bright on black
  • Shift dress
  • Baseball caps
  • Unexpected combos
  • Shorts instead of a skirt
  • Tights and peep-toes
  • Cords for days
  • Sandals, yes, sandals
  • Skinny belts
  • Layering fur
  • Snoods
  • Sparkles
  • Pop your collar
  • Metallics with basics
  • Slouchy socks
  • Say "yes" to white after Labor Day
  • Oversized sweaters
  • Day time cocktails dresses
  • White on white
  • Fashion forward sneakers
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