Martha Stewart’s Glamorously Modern Style Over the Years
Martha Stewart is one of the most iconic homemakers of all time — and, as such, so is her sense of style.
Stewart’s always held a strong sensibility when it comes to color and texture pairings, favoring tonal colors and neutrals that can be mixed and matched throughout the seasons — and even decades, as many of her vintage ensembles wouldn’t be out of place today. The author, cook and pop culture mogul has caved a space for herself with separates like tailored blazers, matte blouses and silky knee-length dresses in hues ranging from olive green to dusky blue, often paired with low-heeled sandals or classic pointed-toe pumps.
In recent years, she’s also leaned into her own penchant for the dramatic — whether stepping out in numerous chic Clergerie wedges for cheeky late-night talk show appearances or draping herself in shimmering sequins to celebrate her historic Sports Illustrated Swimsuit Issue cover. Combined with her top positioning in fields ranging from food to books to television — plus her own frequent viral moments across social media — and it’s clear Stewart is a master at traversing any medium with style.
Below, discover her style’s distinctly smart flair over the years.
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In 1990, Stewart stepped out with daughter Alexis Stewart for the premiere of “Avalon” in New York City. For the occasion, Martha was smartly dressed in an olive green blazer, black trousers and sheer tights, smoothly layered with a brown leather handbag and pointed-toe pumps.
For Vanity Fair and the Tribeca Film Festival’s after party in 2002, Stewart was spotted in olive trousers and a draped gray top, layered beneath a light blue leather car coat. Her tonal outfit was complete with gleaming green emerald stud earrings, a small black clutch and deep mauve open-toed heels.
For a night out at the Metropolitan Opera’s seasonal opening night in 2009, Stewart shimmered in a faintly sheer gown coated in light-catching sequins. The elegant evening wear was paired with a complementary dusky gold sequined jacket and shawl, which the author accessorized with diamond stud earrings, a black leather clutch and deep gold metallic pointed-toe pumps.
In 2019, Stewart made waves at The Blonds‘ fall 2023 fashion show in collaboration with “Moulin Rouge!” at New York Fashion Week. For the occasion, she wore a black blouse and trousers beneath a metallic gold leather biker jacket. Her ensemble was glamorously finished with diamond drop earrings, as well as chunky Clergerie peep-toe wedges crafted from iridescent sparkly fabric.
While out in New York City in 2022, Stewart was seen in a dark brown sweater draped atop light brown leather pants. Her attire was cleverly streamlined with a pair of low-heeled wedge sandals with wide brown leather straps, which she sharply paired with large hammered gold earrings.
In 2023, Stewart made history at 81 as the oldest cover star in history for the 2023 Sports Illustrated Swimsuit Issue. During the magazine’s celebration at the Hard Rock Hotel in New York City, she made a dynamically glamorous entrance in a gold sequined Jenny Packham gown, paired with diamond earrings and mirrored gold platform sandals.
PHOTOS: Discover Martha Stewart’s sharp style over the years in the gallery.
