Big-haired and bright-eyed; Rosie poses for a portrait several years after being discovered on the "Star Search" in 1984.
Rosie is head to toe sparkles at the 12th Annual Cable Ace Awards while walking the red carpet in this ensemble.
Keeping it casual at the Los Angeles "A League of Their Own" premier, Rosie wears an oversized blazer and tan pants.
Showing off her claws, Rosie paws her way down the red carpet at the 44th Annual Emmy Awards in a leopard print ensemble.
Rosie opts for all black with sheer sleeves at the 1993 MTV Movie Awards.
Looking refined and elegant in this floor length trench coat, Rosie attends the 1994 Vanity Fair Oscar Party.
Inspired by Canadian fashion, Rosie sports a Canadian Tuxedo to the premiere of "Losing Isiah" in Hollywood.
In her signature baggy style, Rosie attends the 47th Annual Primetime Emmy Awards in a blue silk suit.
Posing for a picture at the "Harriet the Spy" Benefit, Rosie is spotted wearing her favorite color combo: navy and black.
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.
Opting for a pastel look over neon slime, Rosie waves to fans during the 11th Annual Kids Choice Awards.
Rosie shows her awards night enthusiasm by wearing a metallic gold suit to the 26th Annual Daytime Emmy Awards.
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!
Rosie arrives at the Gilda Club comedy gala in New York City wearing a blue & metallic trench.
Accessorizing with fur, Rosie attends the 4th Annual White Rose Awards Gala with Sesame Street favorite, Elmo, in tow.
Keeping is consistent with darks, Rosie shows off a shorter hairstyle at the 14th Annual GLAAD Awards.
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.
Rosie spotted in a pink coat as she attends an art show at the Pop International Galleries.
Rosie and wife, Kelli, are all smiles as they attend the 2004 Emery Awards.
Rocking pink denim again (but this time without the sleeves) Rosie arrives at the Event to Prevent Benefit.
Rosie keeps it casual as she bundles up in an orange vest when visiting Salt Lake City during the winter months.
Rosie wore a tuxedo-inspired look as she made her way onstage at the 33rd Annual Daytime Emmy Awards.
Rosie relies on her go-to color palette during the Creative Arts Emmy Awards.
Rosie attends her own "For All Kids Foundation" Benefit Cruise, and has some fun with this holiday inspired look.
Rosie and Kelli attend the 18th annual GLAAD Media Awards, both looking chic in black suits.
Rosie is showing passion and emotion while she performs on stage at the True Colors Tour.
Rosie attends a reception to benefit UNICEF, shimmering in this metallic jacket.
Rosie attends the premiere of Lifetime's "America" in chunky boots and a black and navy outfit combo.
We suspect blue is her favorite color, as Rosie wears it as an accent to this otherwise dark outfit!
With a clear love for overcoats, Rosie dresses up her classic black duds with a metallic jacket.
Looking pretty in this white peasant top, Rosie adds some embellishment to what might otherwise be a plain ensemble.
Rosie channels her inner model with that stance (and stare!), rocking a bright red cardigan perfect for the holidays.
Rosie looks lovely in this patterned top and chunky heel.
Rosie wears her fashionable glasses for the "Women Behind Bars" Reading.
Rosie keeps it casual with this black and white jacket over black pants and shoes.
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Former talk show host and actress Rosie O'Donnell is known for many things: Her over-the-top personality, her comedy, and her acting, but there is one thing she's not known for, her adventurous style. It's unlikely that you will find a picture of O'Donnell in a dress and it is even more unlikely that you will find her in a picture wearing color (besides blue)!
The 51 year-old comedian typically arrives on the red carpet in black pantsuits or oversized trenches. O'Donnell has made it a style all her own! Her no-apologies attitude has made her a prolific public figure.
From her on (and off) camera fights with Donald Trump to her outspoken support of gay marriage, Rosie O'Donnell makes sure her voice is heard.
Click through the gallery above to see some of O'Donnell's staple wardrobe moments.