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Martha Stewart's Best Fashion and Street Style

Martha Stewart Is Having a Fashion Renaissance, From Thigh-High Slits to Platforms

Martha Stewart is a tastemaker in her own right who has refused to abide by trends throughout the years. From her '90s cottagecore days (for which there is a dedicated Instagram account) to her recent fashion resurgence as a Sports Illustrated cover model and Fashion Week front-row staple, she stays true to her favourite brands, classic accessories, and innate sense of glamour. At 82, Stewart told Vogue that her mantra is "less is more for a lot of women who are getting older." But we'd argue that she's long been a pioneer for polished and refined dressing with minimal logos.

Stewart counts Brunello Cucinelli and Dennis Basso suiting, Max Mara dresses, Clergerie platform shoes, and Hermès leather shirts as her wardrobe essentials, telling Interview that she maintains a growing collection in the latter category. "They're the most wearable, beautiful, best-made clothing," she said at the spring 2024 runway show, where she debuted a brand-new cashmere jacket from the Parisian house and toted a vintage Birkin from 2001.

Stewart also keeps her old Armani suits in rotation, though she's also not afraid to try something new. Sports Illustrated Swimsuit Issue stylist and costume designer Paolo Nieddu told POPSUGAR that the entrepreneur was more than willing to test out swimwear from Zimmermann and Saint Laurent on set. "Martha has a fabulous décolletage, and as a former print model, she knows how to wear clothes — not the other way around," he said after working with her.

From the ombré sequinned Jenny Packham gown she wore to celebrate her cover, to the sparkling tweed pantsuit she teamed with gold jewellery and metallic heels for an event in NYC, scroll to admire Stewart's notable #OOTDs in recent history, some of which were documented from the entryway of her building — Martha Stewart, she's just like us.

Martha Stewart at Fashion Group International's 39th Annual Night of Stars

Stewart stepped out in New York City on Oct. 17, 2023, in this tweed, sparkly suit by Dennis Basso to celebrate at the Fashion Group International award ceremony.

Stewart made a statement in a little black shift dress from Hermès, Miriam Haskell jewellery, and eyeglasses from her own collection in NYC on Oct. 14, 2023.

Stewart reveled in a leggy moment sporting this shimmering number by Andy Chia Yu. She styled the look with long, dangling earrings and metallic peep-toe pumps.

As a fan of Hermès, Stewart supported the brand during Paris Fashion Week in a white cashmere jacket, vintage silk shirt, and leather pants. Her vintage Birkin bag hails from 2001.

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Stewart attended the event honouring Gabriela Hearst at Lincoln Centre on Sept. 6 in a Brunello Cucinelli pantsuit and Clergerie shoes. Her Cucinelli mesh hat topped off the moment, incorporating a surprisingly sporty element.

Stewart celebrated her iconic Sports Illustrated Swimsuit Issue cover in May 2023 at the Hard Rock Hotel in New York City. She chose a Jenny Packham sequinned gown, Prada shoes, and Harry Winston jewellery for the occasion.

Image Source: Getty / Taylor Hill

In May 2023, Stewart showed off her take on the 3D floral trend in a Carolina Herrera dress, Prada shoes, and an old black fedora, posing in front of her building in New York City.

At the grand reopening of Tiffany & Co.'s flagship store in April 2023, Stewart opted for a Brunello Cucinelli dress with an ornate Oscar de la Renta jacket worn on top to complement her metallic Clergerie platforms.

Stewart accented her chocolate-brown lightweight maxi dress with gold jewellery and metallic platforms at Casa Cipriani on Nov. 7, 2022, in New York City.

Image Source: Getty / Gotham

Stewart sat front row with Kris Jenner on Sept. 12, 2022, to celebrate Dennis Basso's new collection reveal. She wore an embroidered white lace cardigan over a lightweight ivory pants set and finished the ensemble with leather platforms.

Image Source: Getty / Aurora Rose

It's impossible to forget Stewart's Giambattista Valli minidress at the 2020 Vanity Fair Oscar Party. The swingy shift with sheer, tulle sleeves was made even more classy with gold pearls and glittering sandals.

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