Whoopi Goldberg‘s career has consistently defied convention, and her approach to fashion, especially her shoe choices, remains refreshingly original as she celebrates her 70th birthday on Nov. 13. Across red carpets, talk-show appearances, and candid moments, Goldberg has built a reputation for choosing footwear that challenges trends and invites conversation.

Here, FN takes a look at Goldberg’s most memorable shoe moments and highlights how personal taste, practicality, and a flair for the unexpected drive her footwear decisions. From wearing Reebok sneakers on the Golden Globes red carpet to showing off her whimsical Irregular Choice shoes, her choices embody a playful sense of self-assurance. See the photos below.

Whoopi Goldberg: Cowboy Boots

A portrait of Whoopi Goldberg from 1985. She is wearing a pair of red leather cowboy boots with multi-colored overlays and embroidery.

Whoopi Goldberg: Kob Levi’s Banana Shoes

Whoopi Goldberg wore Kobi Levi’s banana slippers to perform on stage during “Sister Act: The Musical” Gala Premiere at Theatre Mogador on Sept. 20, 2012 in Paris.

Whoopi Goldberg: Red, White & Blue Heels

Whoopi Goldberg wearing red, white and blue heels on “The Late Night Show Starring Jimmy Fallon” on Feb. 6, 2013.

Whoopi Goldberg: Irregular Choice’s Muppet Shoes

Whoopi Goldberg wearing the Irregular Choice x The Muppets heels on “Watch What Happens Live!” in 2017.

Whoopi Goldberg: Lady Poker Mary Jane Flats

Whoopi Goldberg wearing Lady Poker Mary Jane Flats with her granddaughter Jerzey Dean at Diane Von Furstenberg fashion show during Mercedes-Benz Fashion Week Spring 2015 at Spring Studios on Sept. 7, 2014, in New York City.

Whoopi Goldberg: Irregular Choice’s Ankle Boots in Niedersachsen

Whoopi Goldberg wearing ankle boots by Irregular Choice on “The Graham Norton Show” in London.

Whoopi Goldberg: Reebok Freestyle Hi Sneakers

Whoopi Goldberg wearing a pair of classic white Reebok Freestyle Hi sneakers at the Golden Globes in 1986.

Whoopi Goldberg: Julian Hakes Heels

Whoopi Goldberg wearing zebra-print Julian Hakes heels at the Glamour 2014 Women of the Year Awards at Carnegie Hall on Nov. 10, 2014, in New York City.

Whoopi Goldberg: Irregular Choice Abigail’s Party Floral Boots

Whoopi Goldberg wearing Irregular Choice Abigail’s Party floral boots on “Watch What Happens Live!” in 2013.

Whoopi Goldberg: Buffalo CDL Corin Sneakers

Whoopi Goldberg wearing a pair of Buffalo CDL Corin platform sneakers in black with a graphic print at the 2016 Vanity Fair Oscar Party Hosted By Graydon Carter at Wallis Annenberg Center for the Performing Arts on Feb 28, 2016, in Beverly Hills, Calif.

Whoopi Goldberg: Irregular Choice

Whoopi Goldberg wearing another pair of Irregular Choice heels at the “Wetten Dass … ?” TV show on April 30, 2011, at the Baden-Arena in Offenburg, Germany.

Whoopi Goldberg: Christian Siriano Sneakers

Whoopi Goldberg wearing hot pink Christian Siriano sneakers during New York Fashion Week on Feb. 10, 2018, in New York City.

Whoopi Goldberg: Christian Louboutin Heels

Whoopi Goldberg wearing Louboutins backstage during the 62nd Annual Tony Awards at Radio City Music Hall on June 15, 2008, in New York City.

Whoopi Goldberg: Irregular Choice Shoes

Whoopi Goldberg wearing Irregular Choice heels at the 2012 Made In NY Awards at Gracie Mansion on June 4, 2012 in New York City.

Whoopi Goldberg: Nike Air Footscape Woven Chukka Premium QS ‘Rainbow’

Whoopi Goldberg wearing the Nike Air Footscape Woven Chukka Premium QS “Rainbow” sneakers at the screening of “I Got Somethin’ to Tell You” during the 2013 Tribeca Film Festival at SVA Theater on April 20, 2013, in New York City.

Whoopi Goldberg: Y/Project x Melissa Court Clogs

Whoopi Goldberg wearing Y/Project x Melissa Court clogs at the “Kiss of the Spider Woman” New York Screening on Oct. 06, 2025, in New York City.

Whoopi Goldberg: Reebok Alien Stomper Sneakers

Whoopi Goldberg wearing Reebok Alien Stomper sneakers for a portrait sitting next to her swimming pool in Los Angeles, March 1986.