These Are the Best Supermodel Street Style Looks of 2019

As the year comes to a close, now is the time to reflect on the greatest style moments of 2019, both on and off the runway.

In recent years, street style has become just as important as the shows, with supermodels such as Bella Hadid and Kaia Gerber sounding off trends after being snapped out and about on the streets.

This year, ’90s style was a big influence on the off-duty looks of supermodels. From head to toe, models were spotted in nostalgic trends such as bucket hats, blazers and square-toe shoes.

Below, FN takes a closer look at some of the key looks the supermodels of the moment pulled off in 2019.

Combat Boots

The utilitarian but chic combat boot was spotted on several supermodels in this year, thanks to the renaissance of ’90s grunge. While off duty, models such as Kaia Gerber continued to wear the same pair of designer kicks while out.

Kaia Gerber, nyc street style, prada bucket hat, jimmy choo cruz combat boots, jeans, celebrity street style, alexander wang bag, Kaia Jordan Gerber steps out New York in mans wearigPictured: Kaia Jordan GerberRef: SPL5094665 310519 NON-EXCLUSIVEPicture by: SplashNews.comSplash News and PicturesLos Angeles: 310-821-2666New York: 212-619-2666London: 0207 644 7656Milan: 02 4399 8577photodesk@splashnews.comWorld Rights
Kaia Gerber in an Alexander Wang blazer, Cruz Jimmy Choo boots paired with a Prada bucket hat and bag, June 2019.
CREDIT: Splash News

Above, Gerber is pictured in the Cruz boot by Jimmy Choo. She was spotted several times this year wearing the shoe, which gave her the perfect edge to her youthfully feminine style.  


The Jimmy Choo Cruz boot.
The Jimmy Choo Cruz boot.
CREDIT: Netaporter.com

The Cruz boot comes in several colorways and while the style like Gerber’s retails for $1,095 on  Netaporter.com, some colorways are now 50% off.

Bella Hadid, pink blazer, button-down shirt, mom jeans, Prada boots, combat boots, celebrity style, street style, New York yankees hat, mini bag, model off duty, Bella Hadid out and about, Paris Fashion Week, France - 30 Sep 2019
Bella Hadid out during Paris Fashion Week, Sept. 2019.
CREDIT: Shutterstock

Prada’s Monolith boots from the fall ’19 collection were also a popular hit this year with the model crowd.

During Paris Fashion Week, Bella Hadid paired the edgy boots with a pink Vivienne Westwood blazer from spring ’20, sunglasses from Oliver Peoples and a classic NY Yankees hat.

Prada fall '19 Fall Footwear Trends 2019 into combat
Prada Monolith Boots
CREDIT: Rex/Shutterstock

The fall ’19 boots from Prada, which come with detachable nylon pouches and a 2.75-inch platform, were also a favorite of Kendall Jenner’s this season.

Square Toes 

But what would 2019 be without square toes? The highly-contested shoe made quite a comeback this year thanks to the demand for ’90s fashion.

Model Hailey Rhode Bieber seen walking in style in sunglasses and a blazer in Beverly Hills.Pictured: Hailey Rhode BieberRef: SPL5134144 061219 NON-EXCLUSIVEPicture by: ENT / SplashNews.comSplash News and PicturesLos Angeles: 310-821-2666New York: 212-619-2666London: +44 (0)20 7644 7656Berlin: +49 175 3764 166photodesk@splashnews.comWorld Rights, No France Rights, No Italy Rights, No Japan Rights
Hailey Baldwin, Dec. 2019.
CREDIT: Splash News

Hailey Baldwin was spotted out and about earlier this month in Yeezy Graphite ankle boots that feature the square toe trend. The model paired the look with a Jill Sander blazer, chocolatey leather pants from Common Leisure, Celine sunglasses and a collegiate sweater.

The off-duty look evoked total Princess Diana vibes, a style icon that served as a huge inspiration for street style this year.

But boots weren’t the only shoe that gave in to the square toe trend, sandals as well were a popular hit among the supermodel crowd.

Kendall Jenner leaves her hotel in New YorkPictured: Kendall JennerRef: SPL5088576 110519 NON-EXCLUSIVEPicture by: SplashNews.comSplash News and PicturesLos Angeles: 310-821-2666New York: 212-619-2666London: 0207 644 7656Milan: 02 4399 8577photodesk@splashnews.comWorld Rights
Kendall Jenner, May 2019.
CREDIT: Splash News

While visiting New York City this spring, Kendall Jenner was spotted in the trend. The “Keeping Up With the Kardashians” star wore a printed top from Acne Studios, straight-leg leather pants from Mugler and strappy square toe Cindy Tie sandals from Rag & Bone.

The shoes are totally ’90s complete with a square toe and chunky kitten heel.

Rag and Bone shoe, square toe trend, super model style
Cindy Tie sandals from Rag & Bone
CREDIT: Courtesy of brand.

What’s next for supermodel street style? FN predicts that our fascination with the ’90s will still rage on thanks to spring ’20’s adherence to such trends like the square toe, so expect the nostalgia to continue.

Here’s to another year of style and to the tastemakers who continue to inspire us to invest in cutting edge trends.

Want more? 

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