Martha's Best Halloween Costumes Through the Years

Martha's Halloween makeup from "Shriek or Chic"
Photo: Brian Bowen Smith

Halloween is our founder's favorite holiday, so it's no surprise that she's the makeover master when it comes to costumes. "From the time I was a little girl, I have loved dressing up for Halloween," Martha said in the October 2018 issue of Martha Stewart Living. "Every year, I look forward to devising my costume—some years the look is elaborate and the ensemble itself is extraordinarily complex, like when I was Fairy GrandMartha or the Spellbinding Sorceress. For those getups, I worked with the editors, makeup artists, costume designers, and seamstresses to execute some pretty ambitious designs."

Surprisingly, some of Martha's personal Halloween costumes also have been thrown together at the last minute and made from simple store-bought materials and her own cosmetics. Here, for example, Martha emerges from her blue satin cloak, eyes aglow behind blue contacts, to shock little ones as they appear at her doorstep.

This year, we pay homage to Martha's many extravagant costumes over the years, from the fantastical to the terrifying.

01 of 16

Fairy GrandMartha

Martha Stewart in her Halloween costume as Fairy GrandMartha

Floating into view on a cloud of pink tulle, Fairy GrandMartha holds her glittery wand at the ready. Like the costumes, this dramatic ensemble is very easy to construct. The tulle is stitched only at the neck; a bodysuit and leggings provide coverage underneath the gossamer layers. Senior stylist Marco Maranghello from John Barrett pinned Martha's hair into a loose updo and then added in extensions and lots of sparkling accents. For a fantastical look like this, he says, "The more hair gems, the better."

02 of 16

Spellbinding Sorceress

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Andrew Eccles

One look at Martha's captivating costume dispels any notion that practicing sorcery means looking like a wicked witch. Bedecked in crystals and stars for the cover of The Best of Martha Stewart: Halloween Handbook, Martha radiates spectral sophistication as a spellbinding sorceress. Her ruched gold stole requires some sewing, but is made of easy-to-find materials; her jewelry is made from Christmas ornaments and crafts-store supplies. Martha wears her own gown; scour vintage or thrift stores for something similarly sparkly.

03 of 16

"Poptastic" Roy Lichtenstein

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Dominik Tarabanski

In 2017, Martha reimagined herself as one of Roy Lichtenstein's iconic comic book women and gave us a behind-the-scenes look in her column for the October issue: "I wore an amazing platinum-blond wig and outlined a plain white shirt with black stripes. Red half-gloves, a bright-blue scarf, and exaggerated makeup added the more cartoonish touches."

04 of 16

Motha

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With a flutter of silk-chiffon wings, a dazzling apparition emerges from the shadows to seek her place in the spotlight. Martha graced the cover of the 2011 Halloween special issue as a Motha, the winged wonder. Inspired by a vintage illustration and pieces from Alexander McQueen collections, she paired a cape and faux-fur collar. Thanks to her platinum-blonde bob wig, flirty butterfly lashes, and enigmatic smile, this chic lepidopteran is naturally luminous.

05 of 16

Ghostly Equestrienne

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Martha was instantly transformed into a haunted horsewoman for the cover of the 2009 Halloween issue. This spirited costume is inspired by the fashion of Edwardian England. Martha's grand cape swells behind her as she rides through a twilight gloaming. Her pale eyes stare from beneath red-rimmed lids. Although the cape looks elaborate, it's constructed with just a few folds and seams in a long piece of taffeta. A top hat veiled with black netting is trimmed with gray ribbon and an ostrich feather. Rutger, Martha's midnight steed, wears an ornately plaited mane.

06 of 16

Queen of the Wild Things

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For season five of The Martha Stewart Show, which aired in 2009, Martha presided over a Monster Bash as Queen of the Wild Things. Her furry costume was inspired by the beloved Maurice Sendak children's book Where the Wild Things Are.

07 of 16

Golden Goddess

Martha Stewart in her Golden Goddess Halloween costume
Craig Cutler

Martha was turned into an autumnal goddess for the "Good Things" cover of the 2007 Halloween issue, draped in a diaphanous wrap of gauzy silk-organza strips and wearing golden leaves in her hair. For the wrap, you can achieve a similar look with a plain, sheer shawl pinned with the brooch. An urn filled with gold-leafed or painted pomegranates, apples, and leaves helps to set the scene.

08 of 16

Medusa

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Medusa, the Greek monster whose gaze could turn people into stone, was Martha's on-air costume of choice in 2008. An intricate and regal headpiece of snakes crowned her stone-colored costume. The show featured a mausoleum of audience members set in bronze, stone, and marble.

09 of 16

Glampire

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Craig Cutler

Dramatic black makeup went perfectly with Martha's glampire getup for the "Bad Things" cover of the 2007 Halloween issue and season three of the show. Her dramatic cape is made from black silk woven with metallic threads. Fasten it to a black dress with safety pins, and slip on long satin gloves. Martha's stylist at the time, Eva Scrivo, trimmed a black wig into textured layers, then gave Martha a pale face, dark eye makeup, and—fittingly—blood-red lips.

10 of 16

Black Cat

Martha as a black cat at Bette Midler's New York Restoration Project's "Hulaween" Gala
Jim Spellman / Getty Images

In 2006, Martha made a fierce-looking feline with this head-to-toe black ensemble: a furry obsidian-black coat, pointed ears on a headband, and a rhinestone collar.

11 of 16

Pajama Party

Martha Stewart at Bette Midler's Annual Hulaween Gala benefit
New York Daily News Archive / Getty Images

Martha loves her farm animals including her five donkeys Rufus, Clive, Billie, Jude "JJ" Junior, and Truman "TJ" Junior—and here, they inspire her costume. At a "Hulaween" gala hosted by Bette Midler, Martha donned a donkey-inspired look with a soft gray hoodie and matching sweatsuit.

12 of 16

Jane of the Jungle

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For the very first Halloween special on The Martha Stewart Show in 2005, Martha dressed up as Jane of the Jungle. Accompanied by a stuffed chimpanzee, she made a grand entrance by swinging on a vine to start the show. Martha has long been a fan of author Edgar Rice Burroughs's Tarzan series.

13 of 16

Sophisticated Spider-Witch

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During a costume-creating segment on Martha Stewart Living in 2003, Martha donned a black Halloween spider veil she created using hat veiling, pom-poms, and chenille sticks.

14 of 16

Pirate

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Sporting a bright-orange bandanna and matching wig, Pirate Martha and her mates took over the Martha Stewart Living set (or rather, ship) in 2003.

15 of 16

Black Widow

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Dressed as a Black Widow for the cover of the 2000 Halloween issue, Martha shows Halloween makeup at its most glamorous and spine-tingling. Her look, achieved with makeup techniques and prosthetic features, was topped off with a swarm of spiders and a set of menacing black nails.

16 of 16

Surfer

Martha Stewart at Bette Midler's 2nd Annual Halloween Ball for New York Restoration Project
Ron Galella / Getty Images

Martha, dressed here as a surfer in 1998, regularly attends Bette Midler's Hulaween gala, benefiting the New York Restoration Project. That year, she wore a form-fitting wet suit, touted a pair of boogie boards, and styled her best beach hair—as if she just stepped out from the ocean.

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