MR PORTER celebrates International Women’s Day with a roundup of some of the most stylish female stars in tailoring.

We love menswear at MR PORTER. It’s a good job really, because we’d lead a very sad existence if we didn’t. But sometimes, it does all get a bit man-heavy, and we wish we got to talk about women a little more. Unfortunately for us, writing about the fairer sex is a privilege usually reserved for NET‑A‑PORTER, but since today is International Women’s Day, we’re throwing such divisive notions out of the office window and celebrating women wearing menswear instead. As such, the women you’ll find below – from Ms Winona Ryder to the late Diana, Princess of Wales – possess a sartorial prowess which transcends the sexes, and can take a suit, shirt or jacket, and teach us simple-minded gents a thing or two about dressing well.

It’s almost remarkable to think that Ms Katharine Hepburn’s androgynous style and penchant for masculine tailoring set her apart from other actresses of her time by flouting gender norms, but it did: “I put on pants 50 years ago and declared a sort of middle road,” she told Ms Barbara Walters in an interview in 1981. Here she is, pictured with Mr Cary Grant on the golf course set of Bringing Up Baby, giving her co-star a run for his money in the trouser department – just look at those sharp creases! Often photographed in tailored jackets, wide-legged trousers or sporty polo shirts, Ms Hepburn’s style was preppy, polished, and nothing short of revolutionary at the time. “I did what I damn well wanted to… and ain’t afraid of being alone,” she told Ms Walters, who asked her if that was why she wore pants. “No,” Ms Hepburn replied matter-of-factly, “I just wore pants because they’re comfortable.”

Considering her startling cheekbones and physics-defying hair, we’re confident that Ms Lauren Hutton would be able to make a Bag For Life look like the item of the season. Regardless of her superhuman magnetism though, the model and actress is an unequivocal master of unbuttoned preppy style and in her 74 years has developed a particular talent for wearing crisp-collared dress shirts and thick wool blazers. This example, a film publicity photo from 1979, is one of our favourites.

Apologies to Prince Phillip – who we’ve written about being a fashion icon on MR PORTER before – but the Princess of Wales steals the crown when it comes to royal style. Favouring an eclectic mix of masculine and feminine looks, Princess Diana wore bowties and dinner jackets as well as she wore vibrant twinsets or soigné evening gowns. The best thing about her style, though, is perhaps its effortlessness – Princess Diana always dressed well, but never looked like she was trying too hard. The British Lung Foundation sweater (which could, in today’s sartorial terms, be an ironic thrift store find) she’s wearing with a cap and jeans here in 1988 speaks to her charitable legacy, which in turn inspired Mr Virgil Abloh to design a line of T-shirts last year for Off-White, decorated with logos of the institutions the princess worked with. A wholesome style icon for the ages if ever there was one.

From her pixie-crop mental patient in Girl, Interrupted to her high-school-ennui-filled character in Heathers, Ms Winona Ryder has been a cultural icon for decades, and she remains in the current collective TV-watching psyche with her recent appearance in Stranger Things. Turning heads for combining red lipstick with men’s blazers, Ms Ryder was reportedly beaten up for her tomboyish dress sense in her youth, and cut her hair short to emulate Bugsy Malone. We’re glad that ugly episode didn’t put her off – here she is in 1991 looking particularly great in an all-black oversized suit.

The fashion industry felt a collective pang of panic when it was announced earlier this year that Ms Phoebe Philo would be stepping down as creative director of Céline. The seminal fashion designer, known for making clothes for intelligent women, is credited with changing womenswear over the past decade and refining it into something cleaner and more powerful. More than that, though, we know no man or woman alive who can wear a rollneck sweater with tailored trousers and a pair of adidas Stan Smiths as well as Ms Philo is doing at the end of her AW12 show in Paris, shown here. She’s also a veritable trendsetter. Ever wondered about the reason white sneakers look so good with trousers these days? You’re looking at her.

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