Martha Stewart's Boldest And Most Scandalous Looks

Since the 1970s, Martha Stewart has been known as a tastemaker when it comes to food, hosting, and entertaining. She is a multi-faceted entrepreneur, serving as the publisher of Martha Stewart Living magazine, writing and publishing over 100 books, and working as a talk show host. And it may be among the more surprising facts about Stewart, but she's made a name for herself as a trendsetter in another area: fashion.

The 84-year-old has had some iconic looks throughout the years, and has become known for her sleek, coastal, and effortless style. Her approach to quiet luxury is usually defined by neutral colors, high-quality fabrics, simple silhouettes, and sophisticated accessories like pearls and diamonds. But sometimes, she surprises fans by stepping out in an ensemble outside her comfort zone. Plunging necklines, high slits, and stilettos occasionally make their way into her sartorial repertoire, providing a fun departure from her usually classic attire. From denim rompers to sequined jumpsuits, read on to revisit some of Stewart's boldest and most scandalous looks.

In 2020, Martha Stewart dazzled at Vanity Fair's famed Oscars Party when she arrived in a striking black minidress with sheer bell sleeves made of tiered tulle. She also wore a layered beaded necklace, drop earrings, and gold open-toed sandals to accessorize the dress. Her smoky eye makeup, glowy skin, and signature layered bob rounded out the look.

The dress was designed by Giambattista Valli, an iconic Italian fashion designer known for breathtaking pieces made of layered tulle. Previous showstoppers include the pink gown that Rihanna wore to the 2015 Grammys, and Ariana Grande's gray showstopper at the 2020 Grammys. The designer called upon similar details — the flowing, layered tulle and dramatic silhouette — to create Stewart's short number.

Though the dress looked striking in photos, it really shone as Stewart walked. That's when the sleeves swung dramatically, adding movement and dimension to the outfit. The minidress also stood out among a sea of gowns, setting the fashion icon apart from the other celebs in attendance. The short hemline showed off her toned legs, which Stewart attributed to horseback riding in an Instagram post of herself in the dress.

Martha Stewart made a splash in 2023 when she was the cover model for Sports Illustrated's famed swimsuit edition. The image, photographed by Ruven Afanador, features Stewart in a plunging, white, V-neck swimsuit topped with a silky, gold wrap. Inside the issue, she's featured wearing a ruched, champagne-colored one-piece with lacing detail, and an oversized floppy hat; a bold, red one-piece with a matching sarong; and a silver-and-black, zip-up one-piece with oversized sunglasses.

This was not the first time the photogenic mogul had posed for the camera. Before Martha Stewart became famous, she worked as a model in her 20s as a way to help pay for college. At age 81, when the cover debuted, she returned to her roots to become the oldest person to grace the cover of this iconic publication. While her age didn't give her any doubts about posing for the shoot, she did amp up her pilates routine and eat a cleaner diet (which may have required limiting Stewart's two must-have store-bought ingredients). "I was motivated by showing people that a woman my age can still look good, feel good, be good," she explained in a behind-the-scenes interview posted to the Sports Illustrated Swimsuit YouTube channel.

Martha Stewart stepped out in an attention-grabbing ensemble for the 2021 Hudson River Park Gala. She turned heads in an oversized, creamy-white double-breasted blazer — but the real showstopper was the feathered trim along each sleeve that gave the outfit a whimsical feel. Bronze, sequined, wide-legged pants rounded out the outfit in a glamorous way.

In signature Martha Stewart style, she took a more-is-more approach to accessorizing the look. Gold and pearl drop earrings adorned her ears while a long, double-stranded pearl necklace hung from her neck.

The gala was held in New York City, at Pier Sixty at Chelsea Piers, and it had a star-studded guest list. The likes of Claire Danes, Julianne Moore, and Susan Sarandon were in attendance alongside Stewart, and they all enjoyed a memorable performance by Grammy winner Wyclef Jean. And Stewart didn't just look good — she and the other attendees helped raise $2.5 million to support local parks' operations and develop new playgrounds.

In 2023, Martha Stewart attended the annual awards show hosted by the Council of Fashion Designers of America (CFDA) in a stunning matching set by Dennis Basso. The American designer, known for his glamorous looks, has dressed iconic celebrities like Nicole Kidman, Jennifer Lopez, Elizabeth Taylor (we've got the low-down on Elizabeth Taylor's favorite foods, if you're interested), and (of course) Stewart.

The full-length jumpsuit Stewart wore to the CFDA Awards had a matching blazer, which added to the drama. Both pieces bore a plaid-like sequined pattern all over that caught the light and gave the ensemble a hint of sparkle and shine. The jumpsuit had a sweetheart neckline, while the blazer had strong, square shoulders; the two created a juxtaposition between masculine and feminine silhouettes that gave the outfit a timeless feel.

While typically an accessory queen, Stewart kept it simple that evening to let the clothing shine. She added only some chunky, sparkly hoop earrings and a simple, black clutch. For makeup, she opted for understated glam: A subtle smoky eye, rosy cheeks, and a nude lip completed the look.

Not all of Martha Stewart's iconic looks come from the runway. While she's worn some beautiful gowns and ensembles to attend galas, premieres, and red carpets, she also dresses stylishly in her day-to-day life — and it's not a new habit. In fact, one her most iconic looks is arguably the denim romper and striped tee Stewart wore when captured at home on her farm in 1976.

The halter-neck romper was fitted at the waist and had micro-mini shorts. Stewart wore a scoop neck, black-and-white striped tee underneath for added coverage. She finished the outfit with slide-on leather sandals and oversized sunglasses — plus a basket of farm fresh eggs, of course.

Interestingly, her ensemble wasn't the only iconic thing about this shot. The farm where this image was taken was her home in Westport, Connecticut, which she owned with her former husband, Andy Stewart. During her time living on the property, Stewart launched a catering company, thus honing the lifestyle and homemaking skills upon which she would build her empire.

Martha Stewart is no stranger to a sequined look; she's stepped out in sparkling outfits before. But this mid-length, sequined cocktail dress may be one of her most show-stopping looks ever.

The shimmering, silver number was designed by Andy Chia Yu, Stewart's neighbor and friend. He first began designing clothes in the late 1980s in New York City, and has made a name for himself with his bold, flamboyant designs that have sold out of iconic stores like Barneys, Saks, and Bloomingdale's. 

This particular dress had a high neckline with an elegant tie, three-quarter sleeves, and a high slit to show off her legs. She paired the dress with matching silver heels and shoulder-skimming, dangling earrings. A metallic clutch completed the look, along with her perfectly coifed signature bob, to attend the Hudson River Park Friends 25th Anniversary Gala in 2023.

Like previous Hudson River Park Friends galas, this was a star-studded affair. Alongside Stewart, notable attendees included Kyra Sedgwick, Alan Cumming, and cookbook lover Sarah Jessica Parker. Together, the attendees helped raise $2.75 million to support the park's events, maintenance, and future care — so not only did Stewart look good that night, but she helped do good, too.

For the legendary Clive Davis' Pre-Grammy Gala in 2026, Martha Stewart chose an outfit that was sure to fit in among the other celebrity guests. The evening featured performances by Grammy greats like John Legend, Art Garfunkel, and 2026 Grammy-winning artist Olivia Dean. However, Stewart told E! News (per an Instagram post) that she was most excited to see Billie Eilish and Bad Bunny take the stage.

For the affair, she donned an extra-glamorous look: a brown sequined Michael Kors gown with a matching fur stole thrown over her shoulder. It isn't the first time Stewart has been seen wearing this famed American designer. Not only has she worn his pieces to other events, she has also attended his shows and even had him on her podcast.

For this soiree, she wore the Michael Kors loose-fitting gown for an effortless, chic vibe. While sleek and stylish, it also maintained the easy, luxurious style that Stewart is known for — but for an evening of glitz and glam, she amped up her look with a diamond necklace, pearl and diamond statement earrings, a matching handbag, and metallic, gold heels. The final look struck the perfect balance between modern and classic.

In 2025, Martha Stewart announced a new business venture: Elm Biosciences, a line of "farm to lab" skincare. Designed in partnership with her dermatologist, the brand has a night cream, serum, and daily supplement to help improve fine lines, firmness, and inflammation.

For the brand's debut, Stewart took to Instagram in a shimmering gold velvet gown. The rounded neckline, long sleeves, and gathered waist made the gown shimmer and highlighted Stewart's glowing skin and golden hair. The dress was designed by independent American sportswear designer Adam Lippes, former creative director at Oscar de la Renta.

Lippes is no stranger to dressing A-list stars, with the likes of Mariska Hargitay and Taylor Schilling walking the red carpet in his ensembles. Stewart even previously wore a very similar dress in a blue hue. But the mesmerizing golden hue of this dress stands out above the rest — so much so that Stewart didn't even need to add many accessories, pairing it with just a simple set of stud earrings.