Martha Stewart's Style Has Completely Transformed Through The Years

Martha Stewart claims her style hasn't evolved much over her decades in the spotlight. "My fashion perspective doesn't really change with age as much as it changes with an inch or two, here or there," she told Vogue in 2023. But we beg to differ. Since she gained notoriety as the nation's favorite lifestyle guru, Stewart's wardrobe matured quite a lot. She's gone from a fashion-forward young adult to a practical yet glam dresser who proves women can rock trends at any age.

Stewart's stylish appearance isn't too surprising, seeing as she's more interested in fashion than many fans may realize. "I've always loved well-made clothes. My attic is chock-full of rack after rack of clothing," she told Footwear News in 2023, revealing she's held on to several vintage designer pieces we'd love to inherit. And, looking back, that penchant for high-fashion has reared its head a few times during her style transformation.

Martha Stewart shot to fame in her 30s and was all about trends. She went full-on '70s fashion in a short, denim, halter neck-playsuit in photos taken at her home in 1976. The beauty showed off her modeling skills (she was a professional model before becoming a lifestyle maven), and even made holding a basket of eggs look high-fashion. She paired the chic one-piece with a navy and white striped top to make the look more modest. She added classic brown sandals and sunglasses that were very of the time. 

That same year, Stewart showed her trendy, feminine side again in a bright red, long-sleeved dress for a kitchen photoshoot. The ensemble was another popular style for the era, as women embraced more color. Stewart kept her look sophisticated and classy, which would become a running theme throughout her style transformation. "I've always been quietly fashionable in a modest way. For 'Entertaining,' it was a vintage dress, and I think the first five covers of my cookbooks were Laura Ashley," she told Footwear News of her early career ensembles.

As Martha Stewart became a household name, she toned down the glam and dialled up the practical ensembles. In her 1986 special "Holiday Entertaining with Martha Stewart," she showed her relatable side by wearing sweaters and jeans, including a casual, brown top and gray pants. But even her most informal outfits were still on trend. She also wore a blue sweater featuring prominent shoulder pads, which were huge at the time (literally and figuratively).

Stewart explained she purposefully opted for sensible looks at work and would never wear designer gear when she knew things could get messy. "I love wearing [Hermès], but I do so much TV in the kitchen and it's such expensive clothing that I don't wear a lot of it in the kitchen," she told Vogue. "That said, I'm not very messy, so I rarely spot anything, but heaven forbid if I wore something like one of my leather blouses. I'd not be happy."

Martha Stewart and risqué outfits may not be synonymous, but we saw a different, daring side to her 1997. The star attended the Emmy Awards in a plunging, all-black two-piece, but made quite the provocative statement by not wearing a top under her suit jacket. She paired the chic, tailored number with sheer socks and peep-toe heels for one of her sexiest looks ever.

This year was all about pantsuits for this star, as she gave us Princess Diana vibes in a deep brown suit she wore to the MTV Video Music Awards. The material had a glam and sophisticated sheen and Stewart again showed her flirty side by revealing her decolletage, though she maintained her modesty with a beige top. She accessorized with black peep-toe heels, but ditched the socks to show a little more skin. By this point, Stewart had become a huge name in Hollywood — she was rubbing shoulders with other A-list celebrities and dating businessman Charles Simonyi following her 1990 divorce, which may explain her more adventurous choices.

Martha Stewart's daring, skin-baring looks didn't last long. By the early 2000s, she'd settled into more conservative outfits that fit her domestic, homey aesthetic. For the American Magazine Conference in 2001, Stewart opted for a practical black turtleneck and matching cardigan, which she paired with sophisticated satin, green pants for a demure pop of color.

Stewart was also spotted that year in a slightly more glamorous look following an appearance on "The Late Show with David Letterman" – but she still ensured it was sensible and practical. Stewart shielded herself from the Big Apple chill in a simple black coat with a fur-look trim, but she added fun in full-sequin black pants that complemented her figure. She paired them with gold pointed toe heels, which were trendy at the time and regained popularity in 2023.

Martha Stewart injected extra sophistication and glamor into her clothes in 2003. During an event at the New York Yacht Club, Stewart showed her edgier side with a leather-look jacket over a gray top, brown skirt, and black ankle boots. She carried a top-handle bag that matched her skirt and added a statement bead necklace (a big accessory trend in the early 2000s). The look was fitting for the star, who was in her 60s at the time, but showed she was still paying attention to trends and wasn't afraid of youthful pieces.

Stewart also demonstrated her versatility at the National Design Awards in 2003. She sported a classy, black-and-white print cardigan over a white top with brown, tailored pants and peep-toe heels. She added a leather and fur-look and wrap, which brought elegance in an unexpected way. The accessory took the look from an unexciting, simple number to a more sophisticated get-up appropriate for the red carpet.

Although Martha Stewart held on to her brown wardrobe long after the 90s style was no longer on trend, she seemed more willing to inject other colors into her outfits by 2007. Spotted outside the Lincoln Center, she wore an elegant mint green jacket, matching shoes, and a knee-length white skirt, which looked stunning and youthful with her coloring. She wasn't ready to totally ditch her beloved neutral brown though, as she carried a snakeskin-print clutch. 

She wore an even bolder ensemble when she attended Preston Bailey's book launch in a daring bright orange coat with a brown bag. Stewart wore the vibrant piece with black heels, black hosiery, and a black dress with a lace trim. Stewart knew how to keep her clothing simple to let the bold outerwear have its moment.

The star was seemingly looking to reinvent her look — and her career — around this time. In 2004, Stewart received a five-month prison sentence for her role in an insider trading case. In 2010, she opened up on "The Oprah Winfrey Show" about her comeback. "I am so grateful that I survived as well as I did. That my company survived. That the rebuilding process that had to take place, not only for me but for all my devoted employees and colleagues, has all taken place and we are recovered," she said.

In 2011, Martha Stewart became a grandmother, and her new role seemingly impacted her clothing choices. Stewart proved she wasn't ready to ditch trends, taking more (sensible) risks with her outfits in 2012. She upgraded her neutral looks with unexpected fabrics, like the shiny, metallic blouse she wore with a dark mustard coat, brown suede pants, and pointed toe heels to the a New York event.  Each piece was elegant and fit her classic style, but combining different textures and adding shine made her muted color palette more exciting.

That same year, she wore an all-beige outfit to the American Made Awards that was also elevated by combining different fabrics. Her shiny top with an oversized collar and matte pants complimented one another without being too matchy matchy, while her metallic heels added a youthful edge.

Martha Stewart let one-color ensembles take over her wardrobe in 2015, when she was in her 70s. And all-black outfits were her favorite. In a 2022 blog post, Stewart explained she found monochromatic dressing a simple way to stay stylish. "Pulling items of the same hue is a quick and easy way to always look put together," she wrote.

Stewart was photographed at the NRF Foundation Gala in 2015 in a black velvet top and pants. The simple two-piece could have been boring and, while definitely a safe choice, she made it more exciting via embellishments on the bottom of the pants and open toed shoes. For a Comedy Central roast that year, she wore flattering black again — with a colorful twist. She sported skinny jeans (one of the year's most popular pants) under a long coat featuring ornate red and purple embellishments. The bright additions helped her avoid a bland look that would have felt underwhelming and stuffy for such a fun entertainment event.

In 2020, Martha Stewart slipped into dark blue jeans with a cream jacket featuring a large, built-in scarf for an event with Seth Rogan. The look was casual but still dignified and tailored to her sensible style. She also kept things understated for The Library of Congress that year in what appeared to be a wide-legged gray jumpsuit. She layered a dark green structured jacket over the top, adding a pop of color via strings of bright gold pearls.

We can't imagine Stewart wearing this look in her 20s, but she's denied the idea that her fashion has changed over the years. "I've dressed the same since I was 17. If you look at my pictures on my Instagram, I look pretty much the same," she told Page Six in 2023. "I don't think about age. I think people are more and more and more [fabulous] than they've ever been in their senior years, and I applaud every one of them," she added. 

In 2022, Stewart launched a clothing line to help others emulate her achievable style. The collection was very in line with her own wardrobe. As she wrote in a blog post, "Every piece is versatile, stylish, and so comfortable."

Martha Stewart may not have a reputation as the ultimate fashion trendsetter, but she certainly embraced trends in her own way in 2024. For the WWD Honors event, Stewart wore an old money-esque cream skirt, ankle boots, bag, and sweater, with a matching coat over her shoulders. The knitwear was the glam-ma's take on the huge sheer clothing trend, as it gave a glimpse at her white top underneath, without straying too far from her demure style. 

She was also on the trend train for the New York premiere of "Martha" that same month, wearing one of her most youthful looks ever. The TV star stunned in a lavender jacket and bold, on-trend metallic pants. The bottoms were baggy, which made them both comfortable and flattering, and fit with fashion's move away from skinny jeans.

Though Stewart's 2024 outfits were youthful and current, she revealed that she'd saved a lot of her old pieces, knowing fashion is cyclical. "I probably have 40 Armani suits that I keep in my collection. I just took out some Hermès suits, probably from 25 years ago — double-breasted blazers and single-breasted blazers, oversized blazers that everybody's wearing now," she told Vogue. "I just dug out a black Hermès suit from at least 25 years ago ... I wear it over a little skinny pants, little black sleeveless top, and it looks like a billion dollars." Oh, how we'd love to raid her closet.