11 Fashionable men who are breaking gender stereotypes

11 Fashionable men who are breaking gender stereotypes

Fashionably fluid

Text: Stephanie Boey Pravin Nair

Image: Getty Images
Image: Courtesy of Saturday Night Live
Image: Alexander Roth
Image: Marc Jacobs
Image: Billy Porter
Image: Tyler Mazaheri

These stylish men are breaking stereotypes through their choices in fashion

What does it mean to dress "like a man"? Many of us grew up under societal pressures that said "blue is for boys, and pink for girls". But really, who decided this? What if the colours were interchanged? Did you know that a hundred years ago, pink was actually the popular choice for boys? An article dated from 1918 stated that it's because "pink, being a more decided and stronger colour, is more suitable for the boy, while blue, which is more delicate and dainty, is prettier for the girl”.

So, in the span of less than a century, society managed to completely change its views on what was deemed "suitable" for men and women. It's a full 180-degree spin, which teaches us that we are capable of unlearning and learning new concepts. 

Could this be the future of fashion? Many stylish celebrities have already exhibited fluidity in their dressing, becoming style icons along the way. If it's socially acceptable for women to wear men's clothing, shouldn't the same rule also apply when the roles are reversed? We think that's true equality! 

Ahead, 11 stylish men who are pushing the boundaries with their fashion choices:

Tyler Mazaheri

Establishing their pronouns across their social media platforms as "he/they", Tyler Mazaheri is a multi-disciplinary artist focused on photography and design that's skewed towards the realm of fashion. The artist utilises womenswear pieces in their day-to-day wardrobe, defining a new standard for gender-fluid dressing. Though it's a simple thing for a man to put on a skirt and call it a day when attempting to defy gender norms, Mazaheri goes on the road less taken by putting on pieces that are contrasting in lengths, design, shapes and patterns.

Marc Jacobs

Known for his time as the Creative Director for Perry Ellis, Jacobs is famous within the fashion world for his grungier takes on clothing. Reflecting this ethos into his eponymous label, the designer dresses to impress himself and those around him in a similar aesthetic. Chunky platformed shoes are paired with pleated skirts, while lipstick and eye make-up are a must-have beauty accompaniment. One also can't forget the striking bags and matching nail polish that goes with all of his looks.

Alexander Roth

Having slowly risen into stardom and becoming an icon within the alternative fashion scene in New York, Alexander Roth is also known for modelling, acting and being a positive disruptor of fashion. Roth does not simply put on a pair of blue jeans and a white T-shirt; the model wears silhouettes that are atypical to the male form. Utilising avant-garde dresses and visibly structured feminine silhouettes, he truly stands out amongst a crowd of regularity.

Billy Porter

Being on the hit TV show Pose where queerness and ballroom culture has been a topic of discussion for seasons, Porter has been a force at breaking gender norms behind and in front of the camera. Having stepped on many red carpets in dresses and gowns that are fit for a princess, Porter has truly stunned the audience and fashion community with his boldness and versatility. Intertwining his queer identity with his ability to style himself as an icon breaking the constructs of gender norms, the actor considers himself to be one of the many pioneers in advocating the non-binary standard of dressing.

Law Roach

Celebrity stylist Law Roach has been dressing up some of the biggest names in entertainment lately, which include Zendaya, Hunter Schafer, and recently, Bella Hadid for the Cannes Film Festival. Roach has also made a mark for himself as a guru in breaking apart the norms that require men to dress a certain way. Always arriving at any party looking amazing from head to toe, the stylist is known for wearing his six-inch Rick Owens heels and wider silhouettes.

Param Sahib

Maximalism is the voice used by designer Param Sahib within his namesake label and so is his personal and individual style. Bold, queer-forward and, more importantly, expressive to his characteristic, Sahib is unapologetically himself, especially when dressing up in very "genderful" clothing. 

Timothée Chalamet

Timothée Chalamet knows how to shut down a red carpet with his statement-worthy looks. But not only that, he continues to keep us guessing every time. His sleek, double-belted suit by Haider Ackermann is one of the most memorable looks from 2019. It's clear the French-American actor also likes to experiment with colours apart from silhouettes. Based on the repertoire of his latest ensembles, the man loves pink. And we love him in it!

Harry Styles

You've heard about the girl with a pearl earring, but have you seen Harry Styles with his? The 'Watermelon Sugar' singer famously wore a single teardrop earring to the Met Gala last year, and we're still thinking about it. As his last name suggests, Styles knows what works for him, and has made pearls his recurring motif. We've been observing him fronting red carpet appearances in a classic string of pearls. Time to dig out grandma's set!

Leo Reilly

You may not know Leo Reilly (yet), but chances are you know his hilarious father. Son of comedian, Jon C. Reilly, the younger Mr.Reilly is paving his own way in the entertainment industry through music. Sweet beats aside, the 22-year-old has an equally interesting taste in fashion. His current favourites are colourful florals, statement ear candy and most recently, peasant dresses.


We first caught wind of Shelhiel, the talented Malaysian singer-rapper/producer at Good Vibes 2019. Entranced by his ethereal electronic sounds and his head-turning style, we predict a superstar in the making. In the 'AAA' music video with Nyk, we see the Kedah-born artist dressed as an off-duty ballerina in a skin-tight leotard, tights and a pink cardigan. Three words: Pulling. It. Off. 

Brian Imanuel

We're so proud that local and Southeast Asian names are on this list! Next up is Indonesian Brian Imanuel, or popularly known as Rich Brian. His style is more subtle and nuanced compared to his counterparts, but we stan a man that dares to wear pink tie-dye and coloured nails.

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