The fascinating stories behind the favourite fashion items of famous women

What we choose to wear often says a lot about us. Here’s what the style staples of six iconic women reveal about them

In her biography of Anna Wintour, author Amy Odell introduces the reader to several fashion items that have found favour with the Vogue editor-in-chief over the years. We’re told of an early obsession with Japanese designers that prompted her to buy the same Kenzo outfit in two colours, a tea-length cream Chanel dress purchased at Bergdorf Goodman for her wedding, and of course, the accessory that she’s seen sporting on the cover of the book–a pair of oversized dark glasses. In the initial chapters, there are several scattered yet memorable mentions of Wintour’s trademark sunglasses, which prove that it was always more than a fleeting phase and an afterthought. One particular detail stays with you long after you put down the book: In a CNN interview, Wintour famously described her glasses as a “crutch” that was useful for when she wanted to hide what she was thinking or feeling. If you look around, you’ll find that, much like Wintour, many famous women, from varied fields, often have that one irreplaceable ingredient in their look that’s accompanied by a fascinating piece of information. We’ve drawn up a list of story-telling staples from Yoko Ono’s hats to Indra Nooyi’s silk saris.

Arianna Huffington and her long-sleeved dresses

A slew of successful men like Barack Obama and Mark Zuckerberg have long subscribed to a sartorial strategy that saves them time. With a wardrobe made of almost identical items, deciding what to wear daily involves little to no effort. However, it isn’t quite as common to hear of women who have been able to adopt a similar, if not the same, approach with ease, and Arianna Huffington is trying to change that. By routinely repeating her collection of versatile, long-sleeved dresses at important events, the CEO of Thrive Global is sending out a message that says it’s just as acceptable, for even the most fashion-loving women, to steer clear of spending a significant amount of time and energy fretting over their outfits every day.

Indra Nooyi and her silk saris

In the early stages of her career, Indra Nooyi interviewed for an internship at consulting giant Booz Allen Hamilton in a turquoise iteration of the six-yard staple. When she landed the role, she wore a sari to work daily even though it often resulted in alienation from others. In her memoir, My Life in Full: Work, Family and Our Future (2021), the former CEO of PepsiCO says, “Taking me to a client meeting in Indianapolis in a sari would have been too jarring in those days. At the time, I fully understood and accepted my colleagues’ leaving me behind. It seemed a small price to pay.” Even decades later, the traditional garment continues to be the hero of Nooyi’s wardrobe, and her first choice for milestone moments–when she was awarded the Padma Bhushan by the then President of India Pranab Mukherjee, she was clad in a lustrous silk sari.

Bandana Tewari and her bracelets

Bandana Tewari, a sustainability activist and Vogue India’s former editor-at-large, is rarely seen without her strong, hard-to-miss stack of bracelets. “My hands are my totem poles. What I wear is not much in terms of price but there’s an abundance of value–valuable narratives and memories of my travels, prayers and longings etched in stone, shell and wood,” says Tewari of the pieces that tell tales of diverse destinations and come together in complete harmony on her wrist. “My bracelet treasures are made with black healing corals from The Banda Islands, volcanic stones from the mighty active volcano Mount Agung, handwoven spirals from Kalimantan in Borneo (the land of orangutans), sacred sacrificial bone from Nigeria, Tibetan metals from Rumtek Monastery in Sikkim, ‘kaanch’ bangles from the village market in Ranthambore, and, of course, my mother’s simple gold bracelet, which always reminds me to stay ordinary with an extraordinary love for the earth we inhabit,” she adds.

Fran Lebowitz and her blazers

Author and protagonist of Netflix documentary Pretend It’s a City (2021), Fran Lebowitz, has followed the same fashion formula since she was in her twenties. It involves brown cowboy boots, jeans (preferably Levi’s 501s) and a crisp button-down topped with the star of her look–a blazer. Her custom-made outerwear changes colour and shape but always comes from the same source–Anderson & Sheppard. Today, the London-based menswear tailor, who hardly ever created clothes for women, has a dummy made to Lebowitz’s measurements.

Yoko Ono and her many hats

Yoko Ono dons many hats–both literally and figuratively. When you look up the Japanese artist, singer and songwriter, your screen quickly fills up with images of her in berets, fedoras and a famous white, wide-brimmed hat she wore when she married John Lennon in 1969. What turned out to be a lifelong obsession with the accessory has its roots in her childhood years. In an interview with Chicago Tribune, she had shared, “The way that hats came into my life is when I was like 4-years-old, my parents always said “make sure that your hat and shoes work together.” When I was a very little girl, I was always wearing a hat.” At 89, Ono still keeps that piece of advice close.

Roohi Jaikishan and her love for all things Gucci

If you scroll through entrepreneur Roohi Jaikishan’s Instagram account, it won’t be long before you’re acquainted with her love for Gucci–a label she has been loyal to since her teenage years. “My parents wore a lot of Gucci and I’ve been wearing their pieces since I was a teenager too–my mom would buy them for me and I would also borrow her clothes and bags,” says Jaikishan. Today, pieces from the Italian fashion house continue to be commonplace in her closet and the allure, adds Jaikishan, lies not only in the refreshing aesthetic of the brand’s creative director Alessandro Michele but also in the label’s conscious commitments. “With its ten-year Culture of Purpose strategy, Gucci is committed to reducing its environmental impact and has also joined the Fur Free Alliance. This makes the brand even cooler,” says Jaikishan, whose next buy is a yellow cardigan from the Gucci and Adidas collaboration.

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