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

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! 

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