Lifestyle Style Last Night's Look: Hit or Miss? Vote on this week's styles including Katie Holmes, Jessica Simpson and more stars! You decide – are they fashionistas or flops? By People Staff Published on December 21, 2009 03:00 PM Share Tweet Pin Email Trending Videos 01 of 31 KATIE HOLMES INF The hits the streets of Beverly Hills in a casual chic mix of plaid flannel and trouser jeans. 02 of 31 JESSICA SIMPSON Arnaldo Magnani/Getty The takes in another performance of her sister Broadway debut in a festive plaid jacket and pleated skirt. 03 of 31 LINDSAY LOHAN Fame The L.A.-based goes back to her roots, visiting N.Y.C. in all black and pin-straight locks. 04 of 31 LEANN RIMES Fame The puts a luxe spin on her basic jeans and T-shirt with her thigh-high boots while out in Calabasas, Calif. 05 of 31 CHLOE SEVIGNY Jose Perez/Splash News Online The Big Love star bundles up against the N.Y.C. chill in a fur-trimmed coat, cuffed jeans and work boots. 06 of 31 CHRISTINA RICCI Flynet The actress is hipster cool in her skinny jeans, patterned cardigan and black sneaks as she runs errands in L.A. 07 of 31 REESE WITHERSPOON Christopher Peterson/BuzzFoto The blends in while visiting New York City in head-to-toe black. 08 of 31 ASHLEE SIMPSON WENTZ INF The adds fun to her casual outfit with a bold houndstooth tote and a red fedora while out in N.Y.C. 09 of 31 MARY J. BLIGE Jerritt Clark/Getty The R&B star stays bundled up in black layers and glam sunglasses at the release party for her album at M2 Ultra Lounge. 10 of 31 JESSICA ALBA Ramey Fitting in some last minute Christmas shopping, stays chic in gray jeans, a loose black pullover and a patterned scarf. 11 of 31 KHLOE KARDASHIAN INF The reality show troublemaker shows off her tough side in thigh-high leather boots, a cropped bomber jacket and studded purse while out in L.A. 12 of 31 RIHANNA Wenn The takes a casual approach topping her black layers with a denim vest while shopping in Beverly Hills. 13 of 31 CHRISTINA AGUILERA Meet The Famous Even divas have casual days! The covers up in a bright turquoise scarf and a newsboy cap while shopping in West Hollywood, Calif. 14 of 31 MARIAH CAREY GSI Media The turns sexy snowbunny in her glam skiwear while vacationing in Aspen. 15 of 31 LINDSAY LOHAN Splash News Online The keeps it casual in black and white on her way to the airport in L.A. 16 of 31 JESSICA SIMPSON Humberto Carreno/Startraks The pairs her Louis Vuitton purse and DSquared jacket with ripped jeans and furry boots for dinner in N.Y.C. 17 of 31 GWEN STEFANI Almasi/Bauer-Griffin The braces against the London chill in her avant-garde Comme des Garcons coat and fedora. 18 of 31 MARY-KATE OLSEN Saleem Elatab-Ahmad Elatab/Splash News Online The bundles up in layers as she hits the streets of N.Y.C. 19 of 31 VICTORIA BECKHAM Startraks lives up to her name for a night at the theatre in London with her family in a black minidress and glamorous fur coat. 20 of 31 KATE HUDSON Fame With her new movie Nine hitting theatres this weekend, the takes a well-deserved break in Aspen in furry boots, an exotic bag and a long henley sweater. 21 of 31 MAGGIE GYLLENHAAL Ray Tamarra/Getty The actress stays wrapped up in an olive coat, black harem pants and a checked scarf while visiting The Late Show with David Letterman. 22 of 31 KATE BECKINSALE Flynet The actress adds a bold graphic edge to her black and gray look with white pumps while shopping at Fred Segal in Santa Monica, Calif. 23 of 31 DIANE KRUGER INF The fashionista keeps it casual in leggings, flats and a double-breasted cardigan for a shopping trip in Beverly Hills. 24 of 31 KRISTIN CAVALLARI Derek Steele/BuzzFoto The Hills hits the streets of L.A. in a relaxed boyfriend blazer over her sexy minidress and red flats. 25 of 31 MARIAH CAREY Fame The goes for fashion over function while vacationing in Aspen in second-skin J Brand jeans, a cropped puffer coat and stiletto, peep-toe boots with rows of fringe. 26 of 31 CHLOË SEVIGNY Jason LaVeris/FilmMagic The actress is her usual daring self in leopard-print pants, a sheer tank, a leather jacket and Bulgari clutch at the My Son, My Son, What Have Ye Done? premiere in L.A. 27 of 31 REESE WITHERSPOON INF The gets into the holiday spirit, hitting the boutiques in L.A. in skinny jeans, a brown sweater and a peacock blue scarf. 28 of 31 VANESSA HUDGENS Frederico Allende/Broadimage The recent is still enjoying herself as she shops on Melrose in a belted red cardigan, Botkier satchel and strappy sandals. 29 of 31 RACHEL BILSON Ramey The takes her casual Elizabeth and James plaid shirt and jeans to the next level with her vibrant orange purse while lunching in Culver City, Calif. 30 of 31 DITA VON TEESE Norman Scott/Startraks The burlesque star flaunts her figure in a fitted cobalt sheath, adding a witty accent with her Union Jack clutch, at a book signing in L.A. 31 of 31 AUDRINA PATRIDGE Flynet The prepares to shoot a scene at a L.A. tattoo parlor in her micro-mini and knee-high boots.