Over the years, Martha Stewart has successfully reinvented herself countless times. Here’s a look back at the evolution of Stewart’s styling from her early days modeling in ’60s, Mad Men-era Manhattan, to her American Gothic life at a farmhouse in Connecticut, to the heady go-go days of the ’80s and ’90s, to her post-prison comeback—and everything in between.

Pictured: 1961
Martha models on a flagpole for Glamour magazine.

Photograph Milton Greene/Conde Nast Archives

Over the years, Martha Stewart has successfully reinvented herself countless times. Here’s a look back at the evolution of Stewart’s styling from her early days modeling in ’60s, Mad Men-era Manhattan, to her American Gothic life at a farmhouse in Connecticut, to the heady go-go days of the ’80s and ’90s, to her post-prison comeback—and everything in between.

Pictured: 1961
Martha models on a flagpole for Glamour magazine.

Photograph Milton Greene/Conde Nast Archives

Martha Stewart: A Career Timeline

Evolution of Style
Evolution of Style

Over the years, Martha Stewart has successfully reinvented herself countless times. Here’s a look back at the evolution of Stewart’s styling from her early days modeling in ’60s, Mad Men-era Manhattan, to her American Gothic life at a farmhouse in Connecticut, to the heady go-go days of the ’80s and ’90s, to her post-prison comeback—and everything in between.

Pictured: 1961
Martha models on a flagpole for Glamour magazine.

Photograph Milton Greene/Conde Nast Archives
Circa 1960s
Circa 1960s

Martha, as an undergraduate at Barnard College, swimsuit edition.

Courtesy Martha Stewart
1976
1976

Martha serves a tray of tomato appetizers.

Photograph by Susan Wood/Getty Images
1982
1982

Martha poses with her first hit book, Entertaining.

Photograph by Dave Darnell/The Commercial Appeal/Landov
1986
1986

Martha presents a turkey on the set of her TV show.

Photograph by Everett Collection
1993
1993

Martha shows off her boots at the Hampton Classic Horse Show.

Photograph by Dafydd Jones
1995
1995

Julia Child joins Martha on the set.

Photograph by CBS via Everett Collection
1999
1999

Martha poses with Bill Johnson, the president of the New York Stock Exchange, on the day her company goes public.

Photograph by Peter Morgan/Reuters
2000
2000

Martha shows off a basket of cut flowers.

Photograph by Terry O'Neill/Hulton Archive/Getty Images
2004
2004

Martha stands behind a marshal outside federal court in New York.

Photograph by Shannon Stapleton/Reuters
2005
2005

Martha wipes away tears as she rejoins her staff after five months in prison.

Photograph by Mike Segar/Reuters
2005
2005

Martha gets final touches of make-up on the set of Larry King Live.

Photograph by Lauren Greenfield/INSTITUTE
2013
2013

Martha poses with former scrap metal exec Daniel Dienst, who Stewart tapped to become her new company’s CEO.

Photograph by Annie Watt