Emmys Fashion: All-Time Best and Worst Looks

Emmys Best and Worst Dressed Ever

Best: Berry Lovely

Even that whole 'Lipstick Jungle' fiasco didn't faze Hollywood pro Brooke Shields. Her appearance at the 2008 Emmys in a stunning raspberry-hued Badgley Mischka gown -- complete with a beaded top and cascading ruffled train -- proves you can't keep a good actress down.

Emmys Best and Worst Dressed Ever

Worst: Straight Up

Before she was judging 'Idol' hopefuls, Paula Abdul was an Emmy-winning choreographer. Too bad she couldn't arrange a better outfit for the '89 Emmys -- her stylist called this hideous white dress with matching long gloves a mix between Cinderella and Audrey Hepburn. In what universe, we're not sure ...

Emmys Best and Worst Dressed Ever

Best: She's Not Blue

Halle Berry -- who won an Emmy in 2000 for 'Introducing Dorothy Dandridge' -- returned to TV's biggest night in 2005 as a double nominee (for 'Their Eyes Were Watching God' and 'Lackawanna Blues') in a strapless blue Ungaro gown with a flowy, cascading ruffle front. Sure looks like a winner to us.

Emmys Best and Worst Dressed Ever

Worst: Falling Out of Love

Jennifer Love Hewitt made it to the top of our worst list, arriving at the Emmys looking ready for the prom in a black and white Carolina Herrera gown with braided detail and a giant messy updo. And before you ask, this was in 2008, not the early '90s. Sigh.

Emmys Best and Worst Dressed Ever

Best: It's the Pitts

Way back in 2000, life seemed so perfect for Brad Pitt and Jennifer Aniston. The 2000 Emmys saw Jen looking effortlessly chic in a red Prada column gown and a low ponytail, and Brad ditching the traditional tie for a "Jen" necklace instead. Ah, to be young and pre-Angelina again ...

Emmys Best and Worst Dressed Ever

Worst: Stepping Out

Accepting a win for her 'Ellen' in 1997 -- the same year her much-publicized coming out episode aired -- Ellen DeGeneres walked the red carpet with then-girlfriend Anne Heche in matching, color-coordinated ensembles and matching, color-coordinated 'dos. We prefer our Ellen with a little more originality.

Emmys Best and Worst Dressed Ever

Best: Pretty in the City

Riding high on her fifth consecutive nomination for Best Actress in a Comedy Series, 'Sex and the City' star Sarah Jessica Parker went even more glam than Carrie Bradshaw in a delicious pale pink meringue-like Chanel confection at the 2003 Emmys. She may not have won the statue, but she did garner serious style praise.

Emmys Best and Worst Dressed Ever

Worst: Wrestle Mania

Who ever told wrestler-turned-actress Chyna Doll that leather and studs were appropriate for the Emmys? The outlandish star's skin-baring look at the 1999 awards show raised a lot of eyebrows and even more questions. Namely, who invited Chyna to the Emmys?

Emmys Best and Worst Dressed Ever

Best: Pretty in Pink

In her 'Law & Order' days, Angie Harmon made a name for herself on the red carpet by ditching the rules. Her eye-catching fuchsia Randolph Duke gown at the 2000 Emmy Awards even had an extra surprise: a gorgeous purple layer peeking out at the hem.

Emmys Best and Worst Dressed Ever

Worst: The Glitter Girl

Emmy-winning actress and performer Barbra Streisand borrowed her 2004 Emmys look from another over-the-top performer: Liberace. Wearing a pink crushed velvet off-the-shoulder gown and matching long cape, the 'Funny Girl' got laughs for a different reason.

Emmys Best and Worst Dressed Ever