Turin-born Gaia Repossi is the creative and artistic director of her family’s jewellery business, Repossi, a role she’s held since 2007. She wears a Bottega Veneta jacket (£1,655) and matching trousers (£570) paired with a bag (£3,460) and shoes (£475) from the Italian house. “This grey oversized suit is filled with identity – it has a loose yet strong appeal to it. It also has a sense of humour with its extra-large fit, as if borrowed from your man in the morning. It’s for tough ladies only!”

Tiffany Hsu wears a Khaite suit jacket with a Bottega Veneta pouch
Tiffany Hsu wears a Khaite suit jacket with a Bottega Veneta pouch © Jonathan Daniel Pryce

Tiffany Hsu, who grew up in Taipei before studying at London’s Central Saint Martins, is the fashion buying director at Mytheresa.com. She wears a checked suit jacket (€1,540) and matching shorts (€639) by Khaite, paired with one of the season’s most wanted accessories: the Bottega Veneta pouch (€980). “I am obsessed with Khaite’s blazer-and-shorts combo, as it’s less serious than a trouser suit, but looks smart at the same time. And who doesn’t love a good power shoulder?”

Amy Sall wears a Petar Petrov jacket and trousers with a Loewe bag
Amy Sall wears a Petar Petrov jacket and trousers with a Loewe bag © Jonathan Daniel Pryce

Amy Sall is a New York-based academic, model and the founder of SUNU: Journal of African Affairs, Critical Thought + Aesthetics. She wears a suit jacket (£841) and matching trousers (£557) by Petar Petrov, shoes by Mansur Gavriel (£405), drawstring bag by Loewe (£1,600) and gold earrings by Completedworks (£415). “Most of my style choices are based on proportions, and Petar Petrov creates the most beautiful silhouettes. Whether I’m wearing one of his suits or dresses, the look always amplifies the confidence and elegance I feel within.”

Alison Loehnis pairs a Prada blazer with Mother jeans and a Saint Laurent T-shirt
Alison Loehnis pairs a Prada blazer with Mother jeans and a Saint Laurent T-shirt © Jonathan Daniel Pryce

Originally hailing from New York, Alison Loehnis is the president of Net-a-Porter and Mr Porter. She wears a double-breasted Prada blazer (£1,950) with wide-leg Mother jeans (£260), a cotton Saint Laurent T-shirt (£220) and suede, heeled sandals by Gianvito Rossi (£575). “I have always been partial to a blazer and love this particular one for its shape – a classic Prince of Wales suiting fabric in a feminine silhouette. It is double-breasted, but not boxy in the slightest.”

Ada Kokosar wears a vintage Michael Kors blazer with an APC T-shirt, Aalto skirt, Chanel handbag and Bulgari watch
Ada Kokosar wears a vintage Michael Kors blazer with an APC T-shirt, Aalto skirt, Chanel handbag and Bulgari watch © Jonathan Daniel Pryce

Ada Kokosar is a Milan-based stylist and the founder of footwear brand Midnight 00. She wears a vintage Michael Kors blazer (similar from £250) with an APC T-shirt (similar from €75), Aalto skirt (similar from £302), Chanel handbag (similar from £3,850) and a Bulgari watch (similar from £6,800). “This blazer is unlined, which makes it feel quite relaxed. I bought it a long time ago when I was living in New York, and it pairs well with everything. Michael Kors is a master of sharp tailoring.”

Milla Loud in a vintage men’s Hugo Boss blazer with vintage men’s Bermuda shorts, sunglasses and earrings
Milla Loud in a vintage men’s Hugo Boss blazer with vintage men’s Bermuda shorts, sunglasses and earrings © Jonathan Daniel Pryce

Milla Loud is a Belgian-Congolese creative director and textile designer. She wears a vintage men’s Hugo Boss blazer (similar from £80) with vintage men’s Bermuda shorts, sunglasses and earrings. “I’ve been a fan of tailoring ever since I had a job where I had to wear a suit every day,” she says. “I also love vintage shopping because you can find something unique and bring new life to it.”

Christine Centenera pairs a Wardrobe.NYC blazer with men’s Louis Vuitton shorts and a Jil Sander bag
Christine Centenera pairs a Wardrobe.NYC blazer with men’s Louis Vuitton shorts and a Jil Sander bag © Jonathan Daniel Pryce

Christine Centenera is the fashion director of Vogue Australia and co-founder of Wardrobe.NYC, which releases seasonal four- and eight‑piece capsule collections. She pairs a Wardrobe.NYC double-breasted blazer (£882) with men’s Louis Vuitton shorts (similar from £620) and a Jil Sander bag (£1,130).

Eva Chen wears a Racil double-breasted houndstooth suit jacket and trousers
Eva Chen wears a Racil double-breasted houndstooth suit jacket and trousers © Jonathan Daniel Pryce

New York native Eva Chen is the director of fashion partnerships at Instagram and a former magazine editor. She wears a double-breasted houndstooth suit jacket (£888) and matching trousers (£410) from Racil and double monk straps ($495) from The Office of Angela Scott.

Julie Pelipas pairs a Balenciaga jacket with a blue Comme des Garçons shirt, brown Le 17 Septembre shirt, Wooyoungmi trousers and a Celine bag (second-hand from £1,500)
Julie Pelipas pairs a Balenciaga jacket with a blue Comme des Garçons shirt, brown Le 17 Septembre shirt, Wooyoungmi trousers and a Celine bag (second-hand from £1,500) © Jonathan Daniel Pryce

Kiev-based Julie Pelipas is a stylist and the fashion director of Vogue Ukraine. She wears a Balenciaga jacket (similar from £1,845) with a blue Comme des Garçons shirt (similar from £350), brown Le 17 Septembre shirt (£260), Wooyoungmi trousers (£703) and a Celine bag (second-hand from £1,500). “This jacket is basically part of my uniform. It goes with everything – sporty sweatpants, skirts or classic trousers – as well as my current mood, which is all about being comfortable.”

Lauren Santo Domingo in a Martin Grant jacket and trousers
Lauren Santo Domingo in a Martin Grant jacket and trousers © Jonathan Daniel Pryce

New Yorker Lauren Santo Domingo is a contributing editor to American Vogue and co-founder of Moda Operandi, which allows shoppers to pre-order from the runway. She wears a jacket ($1,399) and matching trousers ($1,047) by Martin Grant. “Martin Grant has mastered tailoring. I think a tonal look is the ultimate in power dressing.”

Alexandra Carl wears a Rokh blazer with a Prada shirt and Khaite shorts
Alexandra Carl wears a Rokh blazer with a Prada shirt and Khaite shorts © Jonathan Daniel Pryce

Copenhagen-born Alexandra Carl is a stylist and the fashion director of Rika magazine. She pairs her Rokh blazer (£793) with a Prada shirt (similar from £575) and Khaite shorts (similar from £642). “Rokh’s tailoring has so many dimensions and shapes, while still sculpting perfectly through the body and shoulders.”

Caroline Issa wears a Beautiful People jacket and trousers, paired with a Sharon Wauchob shirt
Caroline Issa wears a Beautiful People jacket and trousers, paired with a Sharon Wauchob shirt © Jonathan Daniel Pryce

Montreal export Caroline Issa is a consultant and the chief executive/fashion director of London-based Tank magazine. She wears a jacket (¥102,300, about £765) and matching trousers (about £320) by Beautiful People, paired with a shirt by Sharon Wauchob (£340). “Suiting is my uniform – it requires little effort, but always makes me feel polished and ready to take on the world. I love Japanese label Beautiful People because its tailoring is very precise.” 

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