Dame Emma Thompson, Menswear Guru, Advises to You to Find Your Bliss

Learn a lesson from a British legend.

Emma Thompson wears a black denim jacket white pants and silver sneakers on a blue event carpet in front of a gold...

Emma Thompson in London, November 21, 2022.Joe Maher/Getty Images

There are many attributes that can qualify a woman as a men’s fashion icon, and the simple act of embracing tailored suiting or streetwear is just one of them. Consider Princess Diana, who wore gym clothes and boxy blazers with the same careful precision as she did an evening gown, or Rihanna, who makes anything look about twenty times more swaggy than when anyone else wears it, or Bella Hadid, whose kooky, downtown style has galvanized many a homeboy to wonder where they could, in fact, get it. There is something else—something a little mystifying, a little frizzante—about the way that these women wear clothes, that makes their personal style seem relevant or appealing for men. 

By some metrics, it’s a matter of confidence. It is also true that looser, freer, more comfortable silhouettes tend to feel one-size-fits-all in more ways than one. 

Perhaps, then, one such overarching quality is bliss.

Thompson attends the Matilda The Musical premiere in London on October 5, 2022.Karwai Tang/Getty Images

Consider Dame Emma Thompson, who, like the women above, can more than pull off an evening gown, but also tends to blissfully freak it when it comes to her casualwear. She became a dame wearing a green suit and Stan Smiths. She presented at the Golden Globes barefoot, holding a martini. She loves a cool sneaker and a weirdo oversized shirt. The British actress has herself owned up to not being viewed as a traditional fashion icon, though she accepts this notion comfortably. “At my first Oscars, a fashion reporter said, as I passed along the red carpet: ‘God love her, she always looks so dowdy in anything,’” she once told The Daily Mail. “And I’d made an effort! I wore that as a badge of honor.”

And all of this has only seemed to become truer as Thompson has gotten older, which, in the most ideal scenario, would make anyone feel looser, freer, and more comfortable. This past Monday, while attending a London screening of the Roald Dahl adaptation Matilda The Musical, there was something particularly blissful about how she wore her oversized, raw-hemmed Balenciaga black denim jacket, wide-legged white jeans, and metallic Stella McCartney trainers. (In Matilda, Thompson plays the wicked headmistress Mrs. Trunchbull, who, as typified by Pam Ferris in the 1996 film version, was maybe also sort of an incidental menswear icon.) The outfit allowed for a level of comfort and ease that made it seem natural for her to vamp up and down the carpet with a big ol’ grin. Red carpet mischief…swag…dressing comfortably…not just for the fellas anymore! 

Thompson stands outside Buckingham Palace after receiving her damehood in 2018.WPA Pool/Getty Images
A televised appearance on Sunday Today With Willie Geist, June 19, 2022.NBC/Getty Images

Many of Thompson’s swaggiest pieces—including, most recently, an oatmeal-hued fringed Western jacket and a boxy, psychedelic short-sleeve shirt—have been the creations of her friend, the British designer Stella McCartney, whose womenswear has long held a cool, casual, borrowed-from-the-boys sensibility. The designer, who began making proper menswear not too long ago (Timothée Chalamet is a fan), has carried that ethos throughout her practice; she once said that “there is an element to the menswear that has some humor and lightness to it,” which are perhaps two of the most prevailing facets of bliss

As fashion designers and celebrity stylists have turned towards bigger, baggier, and weirder menswear in the last year, that element of bliss isn’t always visible once the wearers of said menswear hit a red carpet. Humor and lightness can get swallowed up by slouchy double-breasted jackets or oversized trousers, making them feel clownish or heavy. Finding bliss takes practice. But, like most good things, it’s worth the effort.

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