Harry Styles Breaks With Conformity, Makes a Case for Men’s Mary Janes

Harry Styles takes every look to the next level, blurring the lines when it comes to traditional norms of masculine and feminine dressing.

The “Adore You” singer walked the red carpet of the 2020 Brit Awards in London Tuesday, layering a tailored burgundy suit over a purple sweater; under the eggplant-colored top, Styles chose a shirt with a large lace-trimmed collar and baby blue cuffs showing. He accented the look with a white pearl necklace, balancing the tailored shape of the suit with the vintage chicness of his accessories.

Harry Styles, 40th Brit Awards, Arrivals, The O2 Arena, London, UK - 18 Feb 2020
Harry Styles at the 2020 Brit Awards in London.
CREDIT: David Fisher/Shutterstock
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A closer look at Harry Styles’ Gucci shoes.
CREDIT: Shutterstock

The finishing touch on his unparalleled look was a set of classic shoes: Mary Jane flats, a silhouette historically favored by girls and women since the Brown Shoe Company coined the term in the early 1900s. Styles followed the lead of creative director Alessandro Michele, who paired the shoes with trousers and a sweater during the Gucci men’s fall ’20 show in Milan; the black leather style features cutouts on the forefront, a low-profile heel and a cross-foot strap, a signature of the silhouette.

While Styles decided to match the shoe with a textured cream sock, the Mary Jane style was worn on the runway with a taupe textured-knit pair.

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Model on the runway for Gucci men’s fall ’20 show in Milan.
CREDIT: Shutterstock

On top of his arrival look, Styles went with another bold ensemble for his on-stage performance of the ballad “Falling”: a glittering buttoned top with billowy sleeves in ivory, suspenders, matching leaf-adorned textured pants and white sheer lace gloves.

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Harry Styles on stage at the 2020 Brit Awards.
CREDIT: Shutterstock

A third outfit, shared by writer Evan Ross Katz on Twitter, was also pulled from the runway. This time, it was a look from Marc Jacobs’ spring ’20 show: a bright yellow three-piece suit with a tulle violet bow-neck blouse. It was worn by a female model on the runway at New York Fashion Week last September.

The Brit Awards show is far from Styles’ first occasion wearing footwear typically deemed for women. As co-host of the 2019 Met Gala, he chose a black Gucci design topped with frilly lace sleeves and a sheer bodice for a gender-nonconforming look, finished with a single pearl drop earring and block-heeled leather boots. While out in London in May of 2017, he wore a similarly heeled shoe style with a bold patterned suit.

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Harry Styles in a Gucci lace jumpsuit and pearl earring as co-host of the 2019 Met Gala.
CREDIT: Shutterstock
Harry Styles, met gala 2019, shoes, celebrity style
A close-up look at Styles’ shoes.
CREDIT: Shutterstock
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Harry Styles wears loafers with heels and a striped suit on May 12, 2017, in London.
CREDIT: Shutterstock

Click through the gallery to see more red carpet arrivals at the 2020 Brit Awards.

To nail Styles’ daring looks, try any one of these heeled styles for men.

old west heeled boots
CREDIT: Zappos

To Buy: Old West Boots Nashville Boot, $66.

Georgia Boot Logger 8" Waterproof ST w/ Removable Kiltie
CREDIT: Zappos

To Buy: Georgia Boot Logger Boots. $145.

vince heel boots
CREDIT: Zappos

To Buy: Vince Fullington Boots, $195. 

All products featured have been independently selected and curated by our editorial team. If you buy something through our retail links, we may earn commission and the retailer may receive certain auditable data for accounting purposes. 

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