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Martha Stewart is renowned for her individualistic approach to glamour — in fact, down to her shoes.

The homemaking icon’s shoe wardrobe has run a wide gamut over the decades, from sharp pumps to chunky Skechers sneakers. However, her boldest pairs have often been her sleekest, featuring an array of dynamic features: sharp pointed toes, soaring stiletto heels and shimmering metallic palettes.

From the 1990s to the 2020s, all have elevated Stewart’s elegant and luxe attire with a burst of sleek glamour.

In 1990, Stewart mingled with Ivana Trump at the 7th On Sale event to benefit AIDS research. For the occasion, both matched in black minidresses; Stewart’s layered with a chic blazer, pearl post earrings and a white scarf, Trump’s featuring intricate white and yellow geometric trim with duster earrings. Both finished their outfits with classic black pumps, featuring stiletto heels and sharp pointed toes.

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Martha Stewart, style, looks, life, looks over the years, red carpet, celebrity red carpet, opening, awards, awards shows, heels, high heels, wedges, sandals, stilettos, stiletto heels, peep toe heels, fashion

(L-R): Martha Stewart and Ivana Trump attend “7th On Sale” To Benefit AIDS Research at the 69th Regiment Armory in New York City on Nov. 29, 1990.

CREDIT: Ron Galella/Ron Galella Collection via Getty Images

In 2005, Stewart was monochromatically dressed in a deep brown knee-length dress, silky jacket and pearls at a book signing for her title “The Martha Rules: 10 Essentials for Achieving Success as You Start, Grow, or Manage a Business” at Barnes & Noble in New York City. The set earned a slick finish, however, from her choice of footwear: a pair of deep brown leather peep-toe pumps with slingback straps and 4-inch heels.


Martha Stewart, style, looks, life, looks over the years, red carpet, celebrity red carpet, opening, awards, awards shows, heels, high heels, wedges, sandals, stilettos, stiletto heels, peep toe heels, fashion

Martha Stewart hosts a book signing for “The Martha Rules: 10 Essentials for Achieving Success as You Start, Grow, or Manage a Business” at Barnes & Noble Union Square in New York City on Oct. 11, 2005.

CREDIT: Lawrence Lucier/FilmMagic

2020 found Stewart making waves with her outfit at the “Vanity Fair” Oscars party: a black Giambattista Valli minidress with a matte bodice, sheer sleeves and a layered sheer tulle skirt. The frothy piece was paired with layered gold pearl necklaces, as well as a sparkly set of gold glitter-coated heeled sandals.


Martha Stewart, style, looks, life, looks over the years, red carpet, celebrity red carpet, opening, awards, awards shows, heels, high heels, wedges, sandals, stilettos, stiletto heels, peep toe heels, fashion

Martha Stewart attends the 2020 Vanity Fair Oscar Party at Wallis Annenberg Center for the Performing Arts in Beverly Hills, Calif. on Feb. 9, 2020.

CREDIT: Frazer Harrison/Getty Images

In 2022, Stewart glowed with a cool-girl factor at the CFDA Awards, where she sat at Chrome Hearts’ table. For the occasion, the author wore a dark brown long-sleeved midi dress, smoothly layered with a gold chain necklace, tiered cream drop earrings and a brown leather Chrome Hearts clutch. Her ensemble was finished with a pair of mirrored metallic gold platform sandals, complete with crossed-toe straps and thick block heels.


NEW YORK, NEW YORK - NOVEMBER 07: Martha Stewart attends the CFDA Fashion Awards at Casa Cipriani on November 07, 2022 in New York City. (Photo by Dimitrios Kambouris/Getty Images)

Martha Stewart attends the CFDA Fashion Awards at Casa Cipriani on Nov. 7, 2022, in New York.

CREDIT: Getty Images

PHOTOS: Discover Martha Stewart’s sharp style over the years in the gallery.

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