From viral Oxford shirts to Chanel tweed: Men are embracing womenswear – here's why

Last year, a simple Oxford shirt from Uniqlo’s JW Anderson collaboration went viral. Part of the women’s line, its cropped and boxy cut, crisp cotton-rayon blend, and perfectly slouchy silhouette drew raves from fashion creators of all genders. Men began hunting it down in stores, proving that a great fit transcends categories.

Even Uniqlo Singapore caught on, releasing a TikTok featuring a couple in matching Oxford shirts in a cheeky “who wore it better?” post. Australian fashion influencer Joe Fletcher also weighed in on the trend, posting a video of himself trying on the shirts and addressing naysayers directly: “If you’re the guy that’s protesting saying it’s a women’s shirt, don’t wear cropped shirts yada yada – I’m embarrassed for you, man.” The verdict? He was sold on the fit. “They’re chic and super versatile,” he added.

The moment feels symbolic. Even in the age of gender-fluid fashion, women wearing men’s clothes – think boyfriend jeans and oversized shirts – have always been more accepted than the reverse. But today, that boundary is blurring. More men are reaching for slouchy knits, cropped jackets, and jewellery originally designed for women.

Part of this shift stems from frustration. Menswear, for all its precision, can feel formulaic. Womenswear opens up a wider playground of proportions, textures and tones.

“Menswear has certain codes and design ethos that might be limiting for those who are more adventurous,” said Rio Furqan Saini, creative director of Major Minor Agency and BBTBC Studio, which produce fashion campaigns. “Womenswear tends to be more expressive, more boundary breaking.”

THE STAR FACTOR

More male celebrities are integrating women’s clothes into their wardrobe, and doing it with flair.

Take G-Dragon, Chanel’s long-time ambassador, who’s made the house’s signature tweed and jewellery unmistakably his own – no small feat considering Chanel does not have an official menswear line. During his recent Ubermensch World Tour, he performed in a crystal-embroidered Chanel suit, complete with a high jewellery brooch.

Fellow Chanel ambassador Wang Yibo takes a similar approach, wearing the brand’s womenswear pieces in editorials and television appearances. At Chanel’s Fall 2025 show, he turned heads in a black tweed jacket layered with silver and pearl necklaces – a masterclass in genderless chic.

K-pop star Yeon-jun of TXT has made waves speaking openly about his love of skirts and regularly posting photos of himself wearing them on Instagram. In one post, he wrote: “It’s so comfortable. Men can also wear skirts.”

Beyond Asia, artists like A$AP Rocky and Harry Styles continue redefining menswear’s limits. Rocky has turned pearls and quilted handbags into red-carpet signatures, while Styles’ 2020 Vogue cover – where he donned a Gucci dress – cemented his status as the poster boy for fluid fashion.

WHY MENSWEAR ISN’T ENOUGH

Beyond the endless parade of boxy shirts and straight-cut trousers, menswear offers limited silhouettes for men seeking something sculptural or expressive. A classic suit may never go out of style, but it rarely surprises.

Womenswear, on the other hand, embraces possibility. Trousers come wide, pleated, flared, ballooned or tapered. Jackets are cropped, oversized, deconstructed or cinched at the waist. For men seeking novelty – or simply a better fit – the women’s racks often provide what the men’s floor does not.

That’s what drew Louis Zhang, a marketer, to women’s denim at Levi’s and Uniqlo. “I’m on the shorter side, and women’s jeans fit me better – especially mom jeans, which have a roomier cut,” he said. “There are also more colours and options like high-waist [in the women’s section].” His only gripe? “The pockets are too small.”

Two of Furqan’s most-worn pieces are technically womenswear: A Margiela 0 vintage jacket from the Galliano era, prized for its boxy cut and bold print, and a pair of Ami Paris pleated wool shorts that resemble a skirt. Both add movement and intrigue to his daily wardrobe. “These are garments designed for women, but they work better for me than anything I’d find in menswear,” he said.

The appeal also lies in proportion. Often, menswear’s straight lines cater to a narrow, athletic ideal, while womenswear encourages experimentation with waistlines, volume and drape – allowing men to play with balance without looking costume-y.

Then there’s detail: Embroidery, pleats, metallic finishes, bolder colours – all more readily available in womenswear. These touches can turn a look from uniform to individual.

“I’m all about the details,” said Akmal Azilah, a graphic designer who often shops across both sections. “A pleated hem or an unexpected colour can change your whole look. I think a lot of men are realising that subtle doesn’t have to mean boring.”

ACCESSORIES AS THE GATEWAY

For many men, the first step into womenswear isn’t clothing but accessories – brooches pinned to lapels, pearl strands draped over T-shirts, or small shoulder bags styled with oversized suiting have already entered the menswear vocabulary.

Local actor Nick Teo admits his earliest foray into “borrowing” from womenswear was through his wife, actress Hong Ling. “I didn’t own a lot [of accessories] back then, so I kept stealing hers,” he shared in a previous CNA Lifestyle feature. “Even for guys, we can wear something more feminine when it comes to accessories. The first item I borrowed from her was a crystal-studded ring.”

Luxury brands have taken note of the shift. In 2024, Louis Vuitton launched its first fine jewellery line for men, Les Gastons Vuitton. Though positioned primarily for male buyers, artistic director of watches and jewellery Francesca Amfitheatrof has said that its pieces were “also made for women”, a nod to how fluid the category has become.

Meanwhile, Tiffany & Co’s hardware-inspired Lock collection and Dior Men’s crystal brooches continue to blur the distinction between masculine and feminine adornment. After all, a good accessory is never about gender – only attitude.

A MOVE TOWARDS INCLUSIVE DESIGNS

On the runways, more brands are erasing the lines. Ludovic de Saint Sernin’s Spring 2026 collection fused signature lace and corsetry with fluid silks and sequins – worn interchangeably by male and female models – challenging the very idea of gendered dressing. Acne Studios took a subtler route with moody, androgynous tailoring: Suede blazers and whipstitched leather jackets that felt at once sharp and sensual.

At the commercial level, the same idea is filtering down. “Uniqlo U and collections like JW Anderson and Uniqlo C always tend to have great genderless pieces, from pants to jackets,” said Furqan. For many, this is where experimenting feels less intimidating: Affordable, accessible, and without the pressure of high-fashion risk.

“Genderless and unisex should be a cultural norm,” he added. “It’s 2026 – let’s not be so reductive.”

3 PIECES TO SHOP FROM THE WOMEN’S SECTION

BALLOON PANTS

“They’re comfortable, sculptural, and balance proportions beautifully,” said Furqan, who notes that these styles suit most builds. On taller frames, the volume flows elegantly; on shorter ones, the high waist elongates the leg line. He recommends styling these with a simple top, like a cropped jacket or a tucked tee, and ground the look with sneakers or loafers.

STRUCTURED CROPPED JACKETS

This style is perfect for experimenting with proportion. “These create sharp structure: Power at the shoulders, definition at the waist,” shared Furqan. Pair with high-waisted trousers or wide pants for balance, or layer over a longer shirt for a genderless twist.

STATEMENT EARRINGS OR BROOCHES

Accessories are often the easiest entry point into womenswear. A single pearl earring a la Harry Styles, or a crystal brooch adds polish and personality without overwhelming an outfit. Try pinning a brooch on a blazer lapel or a plain tee – a subtle detail that instantly elevates your look.