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16 Looks That Made Winnie Harlow Our Style Obsession

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16 Looks That Made Winnie Harlow Our Style Obsession
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Photo: Getty Images

Winnie Harlow has been bubbling up for a few years now, but it’s safe to say that as of 2018, she has officially arrived. The 23-year-old model made a name for herself with high-profile editorials in pretty much every major glossy, an unforgettable cameo in Beyoncé’s “Lemonade” visual album and, most recently, by becoming Tommy Hilfiger’s newest brand ambassador along with Hailey Baldwin.

But she’s not just a “face.” Harlow is also a vocal advocate of diversity in the fashion and beauty industries, speaking out about both the successes and challenges she faces as a model of color, and as a person with Vitiligo. As Harlow recently wrote on Glamour, “I represent a different standard of what people traditionally consider beauty.”

She has also emerged as one of our absolute favorite celeb style obsessions. Winnie has a chameleon ability to serve everything from a fully glam red-carpet princess to an effortlessly cool ’90s throwback, and pulls them all off with equal panache. She is, simply put, a delight to see. And if she’s not high on your list of style inspirations yet, the 16 looks ahead will surely change your mind.

Pinterest boards ready? Here are Winnie Harlow’s most iconic outfits so far.

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Cinderella Moment
Cinderella Moment

Style watchers had Winnie Harlow on their radar for a few years prior, but this was the moment when everyone sat up and started noticing. Harlow served us a literal Cinderella moment from the Cannes red carpet in 2017, and announced herself as one of the most masterful entrance-makers of all time.

Photo: Samir Hussein/WireImage
Winnie Harlow Street Style
Forward March!

Harlow isn’t just a red-carpet star—we love her casual looks too, and she’s always one of our favorites to look for as she dashes between shows during Fashion Month. There’s something about this military-inspired khaki skirt and tall-boot combo that she wore in Paris last year, which manages to look both badass and playful at the same time.

Photo: Christian Vierig/Getty Images
Winnie Harlow Style
Marilyn Moment

After a few years of red-carpet dominance, we high-key thought we were over the naked dress, but Harlow makes it feel fresh again with this pared-down, fluted silhouette and her adorable pixie cut. Add the icy accessories and flirty pose and this is definitely her “Diamonds Are a Girl’s Best Friend” Marilyn moment.

Photo: Dave Benett/amfAR2017/Dave Benett/WireImage for amfAR
All the Way Up
All the Way Up

The fashion world had been basically obsessed with these slightly-slouchy, ultra-high boots ever since Rihanna wore them on Instagram, but Harlow is definitely tied for best boots with her rainbow-flecked pair, worn with a miniskirt, hoodie and high ponytail. Obsessed with this look.

Photo: Mark R. Milan/GC Images
Winnie Harlow Style
No-Fuss Fancy

One of our favorite things about Harlow’s style is her ability to look fancy without looking fussy. Here, she manages to make a major look out of the bare-minimum elements: Red slip dress, sleek bootie, a single silver bangle. Her understated simplicity makes the other street stylers look try-hard.

Photo: John Lamparski/WireImage
Winnie Harlow Tommy Hilfiger
Earn Your Stripes

On the Tommy Hilfiger runway in Milan earlier this year, Harlow masters the mix of athleisure—those high-waisted joggers—and retro, racing-inspired pieces for a look that’s very “pit crew, but make it fashion.”

Photo: Venturelli/WireImage
Emerald Queen
Emerald Queen

Harlow is a woman who understands the power of being a little extra. In May, at a Cannes screening, she blessed us with this rich, emerald-green silk gown with a fashion-forward wrapped bodice and *just* enough of a train to say, “Make way, lesser beings, a star has arrived.”

Photo: George Pimentel/WireImage
Simple Structure
Simple Structure

Sometimes, simple is best. On her way to the GQ Awards in London, Harlow brought a high-fashion trend—the strongly structured, intricately laced dress—straight down to earth with black heels, minimal accessories, and her beaming smile.

Photo: Mark Milan/GC Images
Out of this World
Out of this World

The ideal example of how to do night-out casual: the NASA sweatshirt is cute and comfy, but the sick lace-up heels and elegant sandy color palette make it clear this is no mere errand-running outfit.

Photo: Ricky Vigil M/GC Images
White Out
White Out

Go ahead, name a person who has ever looked more divine in an all-white outfit than Harlow attending a fashion show in Berlin—we’ll wait. Please also do yourself a favor and notice that those boots go alllll the way up, stopping just below the pockets of her jeans. We are unworthy of this space-age angel.

Photo: Andreas Rentz/Getty Images for HUGO
Strike a Pose
Strike a Pose

Fun fact: Harlow is not actually strutting the runway at this fashion show in Paris. Nope, she was merely perched front row, and when asked for a pic, she rose and struck this iconic pose to show off her romantic, fluttery floral dress to its full advantage. Let it be a lesson to us all: Always know your angles, and never be afraid to show a little gam.

Photo: Stephane Cardinale/Corbis/Getty Images
Living in 3018
Living in 3018

At the Solo premiere in May, Harlow embraced the film’s futuristic vibe with this exquisite gown. We’ve never seen a train quite like it—so fluid, it appeared to trail down the steps like molten silver.

Photo: Tony Barson/FilmMagic
Romper Room
Romper Room

Another example of Harlow’s prowess with the casual going-out outfit, we love this military-style romper worn with a wide belt, teeny box bag, and that faux-fur coat practically falling off her arms in a way that is inexplicably, but undeniably, glamorous.

Photo: Mark R. Milan/GC Images
'90s Throwback
'90s Throwback

Remember what we said about Harlow making all the other street style stars look try-hard? Here, she does it again with a super-basic white tank and jeans outfit, subtly elevated to ‘90s-throwback masterpiece via those high-top sneakers, fanny pack, and Lil’ Kim-style shades. Well done, Winnie!

Photo: Edward Berthelot/Getty Images
Fresh and Clean
Fresh and Clean

Harlow knows the way to stand out in a sea of all-black dresses: wearing clean, bright white from head to toe, and topping things off with a robin’s egg-blue motorcycle jacket. It’s pretty and tough at the same time.

Photo: Mark R. Milan/GC Images

And finally, your fall inspiration. Back in February 2017, Harlow stomped it out on the streets of Soho in sleek black leather leggings, an oversized faux fur coat, and flannel, giving us classic model off-duty vibes. This look is so New York it’s practically waiting in line for a cronut.

Photo: Alo Ceballos/GC Images

Next slideshow starts in 10s

Standout Beauty Looks Spotted at NYFW Spring 2019

Standout Beauty Looks Spotted
at NYFW Spring 2019
  • Cinderella Moment
  • Winnie Harlow Street Style
  • Winnie Harlow Style
  • All the Way Up
  • Winnie Harlow Style
  • Winnie Harlow Tommy Hilfiger
  • Emerald Queen
  • Simple Structure
  • Out of this World
  • White Out
  • Strike a Pose
  • Living in 3018
  • Romper Room
  • '90s Throwback
  • Fresh and Clean

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