As far as Hollywood legends go, Marlene Dietrich ranks among the greatest. Renowned for her performances on stage and in silent films during the 1930s and 1940s, she pioneered the femme fatale archetype. And off-screen, her personal style combined that fierce femininity with masculine-inspired tailoring to striking effect. When she wasn’t adorning herself in glittering eveningwear and feather boas, she often wore full suits, typically nipped in at the waist and accessorised with a tie, hat and pocket square that perfectly complemented her slim brows, cropped haircut and precisely painted face. This look was unusual for women of her era, yet Dietrich challenged norms to the extent that the concept of androgyny is often associated with her name, even today.

Becoming a muse for Bottega Veneta, Chanel and LOEWE in one fell swoop would be overachieving for some. But The Bear and After The Hunt star Ayo Edebiri makes it look oh so easy. On the red carpet, she favours two-piece suits, vintage-leaning garb and, sometimes, jeans. When stepping out between meetings, dinners and events, she wears The Row and Khaite, known for their stripped-back, quiet-luxury cool. Her put-together but boyish charm means even a long-sleeve white tee and boxy board shorts look like the height of sporty-chic, with anti-paparazzi sunglasses giving her daytime ensembles a sleek and sophisticated finish.

From the dizzy heights of Glastonbury’s Pyramid Stage to the Miuccia Prada-approved runways of Paris, Little Simz always turns out a look. But it’s never what you expect. The rapper, actress and now high-fashion model – she’s walked on the Miu Miu runway – keeps us on our toes with her experimental style, which can go from sporty to geek-chic, suited and booted, and back again. Ever the non-conformist, she turns to Prada and of course Miu Miu to kit her out, blending their signature cerebral style to inform her red-carpet fits. If she’s wearing a suit, let it be known that it won’t be plain. Take this ensemble: a feather-trimmed black blazer, wide-leg trousers, a tie and a box-fresh shirt, finished with quintessential yet subversive lugged-soled loafers. It’s a spin on a classic, but Little Simz to a tee.

“The girl from Croydon” has appeared on billboards, mood boards and bedroom walls since the 1990s. And we’re still keeping tabs on Kate Moss’s off-duty looks and red-carpet ensembles in 2026. The powerhouse British supermodel still rules on the runway, but when she’s not modelling, she will often be sat on the front row, watching a new generation attempt to fill her shoes. Muse to Anthony Vaccarello, the creative director of SAINT LAURENT, Moss often wears his take on the Le Smoking suit, a satin-trimmed tuxedo jacket with big shoulder pads and, well, not much else. She might wear this as a dress, complete with Ray-Ban Wayfarer sunglasses, large gold hoop earrings and her signature blonde beachy waves. Once a supermodel, always a supermodel.

The red carpet is like high art for actor and singer Zendaya, and her fashion choices are never short of scene-stealing. With seven Met Gala appearances under her belt, a stash of highly prized awards and an enviable filmography (catch her in The Drama, Dune 3 and the new season of Euphoria this year), it’s safe to say Zendaya is a modern megastar. Style-wise, she’s a maverick, and alongside her longtime collaborator, the stylist Law Roach, she steps out in looks that make everyone else’s pale in comparison. Take her outfit from the 2025 Met Gala, where she stepped out in a razor-sharp white suit, topped with a floppy fedora and sparkling jewellery. It was reminiscent of Bianca Jagger’s boho wedding suit for her marriage to Sir Mick Jagger, as well as Diana Ross’s character in the film Mahogany, both of which are 1970s icons.

If you’re not watching Ryan Murphy’s new show, Love Story, what are you waiting for? Following the star-crossed relationship between John F Kennedy Jr, he of presidential lineage, and the Calvin Klein-clad Carolyn Bessette, you may find yourself yearning for a love affair like theirs, and maybe even a slice of their iconic style. CBK’s days working at the Calvin Klein office in Midtown NYC informed her personal style along with her husband’s wardrobe – pairing pencil skirts with men’s poplin shirts was her forte. The rest of her wardrobe consisted of a minimalist mix of straight-cut jeans, single-breasted wool coats and V-neck merino sweaters. No one did it like Bessette Kennedy, but you can emulate her look today, and maybe even that of her other half’s, by way of The Row, Mr P. and Polo Ralph Lauren.

Julia Roberts changed the red-carpet game with her appearance at the 1990 Golden Globes. Eschewing the typical gown associated with such star-studded events, the Pretty Woman actor picked up an off-the-rack grey suit by Giorgio Armani (from the men’s department, of course) and had it tailored in-store. She then teamed it with a white shirt, a patterned tie and brown Oxford brogues, unwittingly searing this red-carpet moment into the Hollywood and pop-culture memory at large. Armani’s relaxed but ever-modern tailoring was legendary long before this moment – see American Gigolo – but Roberts opened the floodgates for the cool girls to give the look a try. Hailey Bieber, Rosie Huntington-Whiteley and Charli XCX have since been spotted giving the corporate-realness vibe a test drive. Only Roberts, though, remains the original.

The perennial “girl next door” has been pinching pieces from the menswear aisle for some time – and we are starting to take notice. When the Materialists and Madame Web star is not cloaked in Gucci for red-carpet appearances, Dakota Johnson is routinely pictured in items we want to add to our basket yesterday. Think vintage-feel trench coats, Polo Ralph Lauren baseball caps, blue jeans, gum-sole sneakers, preppy knitwear, John Lennon-style sunglasses and perfectly worn-in tees. It’s that heady blend of 1970s shapes, knowing 1980s nods and 1990s sensibilities that she just gets so right, every single time.

Often dubbed the “queen of menswear”, the late Diane Keaton wore a suit better than most. It all started with her star turn in 1977’s Annie Hall, which her sees her titular character dressed in natty shirts, ties, waistcoats, wide-brimmed hats and pleated trousers. Keaton was Annie, and Annie was Keaton; it was a look that unequivocally set the tone for the rest of the actor’s distinctive fashion. It also led to her sitting front row at many a fashion show, including those of Thom Browne and Ralph Lauren, both of which aligned perfectly with her sharply tailored, often beautifully eccentric, personal style.