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Kentucky Derby Hat: Jaime Pressly, 2006  We’re getting an Audrey Hepburn vibe from Jaime Pressly’s classic look. OK, fine, maybe just from the neck up.

20 of the Most Memorable Kentucky Derby Hats Seen on Celebrities

Kentucky Derby Hat: Jaime Pressly, 2006 We’re getting an Audrey Hepburn vibe from Jaime Pressly’s classic look. OK, fine, maybe just from the neck up.

Jaime Pressly's Changing Looks - 2016 from InStyle.com

Jaime Pressly's Changing Looks

Jaime Pressly's Changing Looks - 2016 from InStyle.com

Bombshells: Jaime Pressly, Angie Harmon and Maggie Gyllenhaal all donned revealing gowns at the 5th Annual Critics' Choice Television Awards on Sunday

Cleavage reigns supreme at the Critics' Choice TV Awards red carpet

Bombshells: Jaime Pressly, Angie Harmon and Maggie Gyllenhaal all donned revealing gowns at the 5th Annual Critics' Choice Television Awards on Sunday

This length would work great for work

This length would work great for work

jaime pressly

jaime pressly

Pulling a Miley: Jaime Pressly chopped off her honey blonde locks again, sporting the Mile...

Jaime Pressly copies Miley and shaves sides of her head

Pulling a Miley: Jaime Pressly chopped off her honey blonde locks again, sporting the Mile...

Jaime Pressly Photos: "The Lego Movie" Premiere

Jaime Pressly Photos Photos: "The Lego Movie" Premiere

Jaime Pressly Photos: "The Lego Movie" Premiere

jaime pressly

jaime pressly

Jaime Pressly attends the Variety and Women in Film Pre-Emmy Event at Scarpetta on Friday, Sept. 21, 2012, in Beverly Hills, Calif.

Jaime Pressly attends the Variety and Women in Film Pre-Emmy Event at Scarpetta on Friday, Sept. 21, 2012, in Beverly Hills, Calif.

Ombre effect: Jaimie Alexander was dressed in Halston Heritage

Cleavage reigns supreme at the Critics' Choice TV Awards red carpet

Ombre effect: Jaimie Alexander was dressed in Halston Heritage

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