Celeb Fashion Hits & Misses

Check out recent triumphs and trip-ups by Katie Holmes, Nicole Richie, Gwyneth Paltrow and others. By Serena Kappes

01 of 12

KATIE HOLMES: HIT

KATIE HOLMES: HIT
Jean/allactiondigital/Retna

Katie Holmes dazzles in a diaphanous Chloé dress and Christian Louboutin heels at fiancé Tom Cruise's War of the Worlds premiere in London.

02 of 12

NICOLE RICHIE: HIT

NICOLE RICHIE: HIT
Tuan Pham/x17

Nicole Richie keeps it short and simple in a strapless red minidress with a waist-cinching gold belt and matching clutch in Beverly Hills.

03 of 12

JANET JACKSON: MISS

JANET JACKSON: MISS
Fitzroy Barrett/Globe

We're sorry, Ms. Jackson, but that skirt is just not flattering. The singer looks like she has curtains strapped to her hips at a Beverly Hills charity gala.

04 of 12

GWYNETH PALTROW: HIT

GWYNETH PALTROW: HIT
Camilla Morandi/REX

Gwyneth Paltrow is angelic in a beaded Valentino gown with a delicate chiffon overlay at a fashion event in Rome.

05 of 12

HILARY DUFF: MISS

HILARY DUFF: MISS
Chris Wolf/DailyCeleb

Leg warmers in summer? Eek. Hilary Duff makes a fashion faux pas with her sundress-winter accessory combo at a Hollywood club.

06 of 12

GABRIELLE UNION: HIT

GABRIELLE UNION: HIT

The Honeymooners star Gabrielle Union glows in a silky Hugo Boss slip dress during an appearance on Last Call with Carson Daly.

07 of 12

NICOLLETTE SHERIDAN: MISS

NICOLLETTE SHERIDAN: MISS
Bauer-Griffin

Desperate Housewives actress Nicollette Sheridan's legs look like they're imprisoned by her gown's peek-a-boo stripes at the L.A. premiere of Mr. amp Mrs. Smith.

08 of 12

JENNIFER CONNELLY: HIT

JENNIFER CONNELLY: HIT
Brian Prahl/Splash

Jennifer Connelly channels Audrey Hepburn in an elegant A-line Chanel dress with a festive silk bow at a charity gala in New York City.

09 of 12

MYA: MISS

MYA: MISS
Stewart Cook / REX

My, oh, Mya! The singer-actress takes whimsical a bit too far in a tacky lingerie-esque minidress at the MTV Movie Awards.

10 of 12

RACHEL BILSON: HIT

RACHEL BILSON: HIT
Charley Gallay/LEP/Splash

The O.C. star Rachel Bilson goes retro in a 1940s-style Derek Lam dress and peep-toe pumps at a party in Hollywood.

11 of 12

SARAH MICHELLE GELLAR: HIT

SARAH MICHELLE GELLAR: HIT
Robin Platzer/Twin Images

Sarah Michelle Gellar is glamorous in a silky chocolate-brown Max Azria Collection gown festooned with rhinestone brooches and silver-and-gold pearl strands at the CFDA Fashion Awards in New York City.

12 of 12

PARIS HILTON: MISS

PARIS HILTON: MISS
Adrian Varnedoe/Pacificcoastnews

Paris Hilton isn't making a rainbow connection in a strapless minidress that looks more like a feather duster at West Hollywood restaurant Koi.

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