Rosie O'Donnell's Style Transformation

1988

Big-haired and bright-eyed; Rosie poses for a portrait several years after being discovered on the "Star Search" in 1984.

January 1991

Rosie is head to toe sparkles at the 12th Annual Cable Ace Awards while walking the red carpet in this ensemble.

June 1992

Keeping it casual at the Los Angeles "A League of Their Own" premier, Rosie wears an oversized blazer and tan pants.

August 1992

Showing off her claws, Rosie paws her way down the red carpet at the 44th Annual Emmy Awards in a leopard print ensemble.

June 1993

Rosie opts for all black with sheer sleeves at the 1993 MTV Movie Awards.

March 1994

Looking refined and elegant in this floor length trench coat, Rosie attends the 1994 Vanity Fair Oscar Party.

March 1995

Inspired by Canadian fashion, Rosie sports a Canadian Tuxedo to the premiere of "Losing Isiah" in Hollywood.

September 1995

In her signature baggy style, Rosie attends the 47th Annual Primetime Emmy Awards in a blue silk suit.

July 1996

Posing for a picture at the "Harriet the Spy" Benefit, Rosie is spotted wearing her favorite color combo: navy and black.

April 1997

Never one to shy away from a good time or a good cause, Rosie proudly sports her new makeover backstage at the 1997 Kids Choice Awards.

April 1998

Opting for a pastel look over neon slime, Rosie waves to fans during the 11th Annual Kids Choice Awards.

May 1999

Rosie shows her awards night enthusiasm by wearing a metallic gold suit to the 26th Annual Daytime Emmy Awards.

April 2000

While we certainly all have a hoodie or two in our wardrobe, we cannot help but wonder why Rosie brought one to the red carpet!

November 2001

Rosie arrives at the Gilda Club comedy gala in New York City wearing a blue & metallic trench.

November 2001

Accessorizing with fur, Rosie attends the 4th Annual White Rose Awards Gala with Sesame Street favorite, Elmo, in tow.

April 2003

Keeping is consistent with darks, Rosie shows off a shorter hairstyle at the 14th Annual GLAAD Awards.

February 2004

Adding a bit of color to her wardrobe with a bouquet, Rosie walks hand-in-hand with her longtime girlfriend, Kelli Carpenter, shortly after their private wedding ceremony.

May 2004

Rosie spotted in a pink coat as she attends an art show at the Pop International Galleries.

December 2004

Rosie and wife, Kelli, are all smiles as they attend the 2004 Emery Awards.

 May 2005

Rocking pink denim again (but this time without the sleeves) Rosie arrives at the Event to Prevent Benefit.

January 2006

Rosie keeps it casual as she bundles up in an orange vest when visiting Salt Lake City during the winter months.

April 2006

Rosie wore a tuxedo-inspired look as she made her way onstage at the 33rd Annual Daytime Emmy Awards.

August 2006

Rosie relies on her go-to color palette during the Creative Arts Emmy Awards.

December 2006

Rosie attends her own "For All Kids Foundation" Benefit Cruise, and has some fun with this holiday inspired look.

March 2007

Rosie and Kelli attend the 18th annual GLAAD Media Awards, both looking chic in black suits.

June 2007

Rosie is showing passion and emotion while she performs on stage at the True Colors Tour.

February 2008

Rosie attends a reception to benefit UNICEF, shimmering in this metallic jacket.

February 2009

Rosie attends the premiere of Lifetime's "America" in chunky boots and a black and navy outfit combo.

April 2009

We suspect blue is her favorite color, as Rosie wears it as an accent to this otherwise dark outfit!

February 2011

With a clear love for overcoats, Rosie dresses up her classic black duds with a metallic jacket.

April 2011

Looking pretty in this white peasant top, Rosie adds some embellishment to what might otherwise be a plain ensemble.

December 2011

Rosie channels her inner model with that stance (and stare!), rocking a bright red cardigan perfect for the holidays.

January 2012

Rosie looks lovely in this patterned top and chunky heel.

May 2012

Rosie wears her fashionable glasses for the "Women Behind Bars" Reading.

December 2012

Rosie keeps it casual with this black and white jacket over black pants and shoes.