Fashion October 2006 By InStyle Editors InStyle Editors Facebook Instagram Twitter Our editors and writers comprise decades of expertise across the beauty, fashion, lifestyle and wellness spaces in print and digital. We prioritize journalistic integrity, factual accuracy, and also having fun with every story we share. InStyle's editorial guidelines Updated on April 2, 2015 @ 01:17PM Pin Share Tweet Email Trending Videos Photo: Matt Baron/BEImages October 2006 01 of 23 Jessica Simpson David Dyson/Camera Press Jessica Simpson was dressed in the latest trends (plaid, wide belt and tall boots) as she made her way to the airport in London. The singer hit a high note with the leopard-accented Louis Vuitton bag she was toting.Click to Buy the Look 02 of 23 Drew Barrymore Jon Kopaloff/FilmMagic Sexy goes without saying, but Drew Barrymore brings glamour back as well in a luxe one-shoulder frock by Diane von Furstenberg, at a Sony party in Beverly Hills. The actress accented her look with diamonds and pearls from Bulgari, a gold clutch by Calvin Klein and a pair of Manolo Blahnik d'Orsay pumps in a demure hue.Click to Buy the Look 03 of 23 Eva Mendes Jon Kopaloff/FilmMagic Eva Mendes looked charming in a Salvatore Ferragamo dress and soft curls at the Sony gala in Beverly Hills. The actress accessorized her flirty look with a metallic belt and clutch also by Ferragamo and square-toe pumps by Sergio Rossi.Click to Buy the Look 04 of 23 Emmy Rossum Splash News Venus de Milo? Not quite, though Emmy Rossum arrived at the Christian Dior fashion show in Paris looking very statuesque. Paying homage to the design house, the actress wore a Christian Dior dress with earrings by Harry Winston and a Robert Bruce Bielka ring.Click to Buy the Look 05 of 23 Sienna Miller Reg Vagas/CelebrityPhoto Sienna Miller showed serious style when she attended the Pepe Jeans party in a black tailcoat, a leather harness-like belt and knee-high boots, as an army of paparazzi looked on. The British actress was recently named the new face of the brand.Click to Buy the Look 06 of 23 Katie Holmes Patrick Dunlop/Splash Katie Holmes looked sharp in a crisp white suit and black shirt by Yves Saint Laurent. The actress has been hitting the shows at Paris Fashion Week with pal Victoria Beckham.Click to Buy the Look 07 of 23 Jennifer Lopez Sara De Boer/Retna Jennifer Lopez looked glamorously sexy in a black Versace dress, with smoky eyes and long, straight locks. The actress was attending the Childrens Hospital Los Angeles charity gala in Beverly Hills.Click to Buy the Look 08 of 23 Naomi Watts Henry Lamb/BEImages Naomi Watts looked sweet and innocent as she strode along the red carpet at the Infamous première in New York City. The actress paired a knee-length Calvin Klein dress with a Juicy Couture jacket and Marc Jacobs mary janes.Click to Buy the Look 09 of 23 Sarah Michelle Gellar Bill Davila/Startraks Sarah Michelle Gellar rocked the latest trends (knee-high Chloé boots worn over J Brand skinny jeans) while stepping out of MTV studios after appearing on TRL. The actress's Lorraine Schwartz necklace was a bright spot in her otherwise inky ensemble, which included a Chloé blouse.Click to Buy the Look 10 of 23 Heather Graham John Ricard/Retna Heather Graham created a sexy yet cozy fall look with this cap-sleeved sweater dress, textured tights and knee-high Versace boots. The actress, who was attending an Audi event in New York City, was flushed with bright cheeks and a brick-red pout.Click to Buy the Look 11 of 23 Michelle Williams Henry Lamb/BEI Michelle Williams brought some indie spirit to Manhattan's Madison Avenue for the launch of Gold, the new perfume by Donna Karan. The actress walked (and matched) the black carpet in a deconstructed dress and cropped cardigan from Karan's DKNY line.Click to Buy the Look 12 of 23 Joy Bryant Gregg DeGuire/WireImage Joy Bryant looked quietly sexy on the red carpet at the 21st Annual American Cinematheque Award dinner. The actress opted for a form-fitting vintage dress by Hervé Léger and kept her glamorous look youthful by wearing her hair in loose waves.Click to Buy the Look 13 of 23 Jennifer Aniston Sara De Boer/Retna Jennifer Aniston was free of frills at the Glamour Reel Moments Short Film Series event in L.A. The actress displayed a simple sophistication in a Chloé top with Versace pants and shoes. She accessorized the look with a Roger Vivier bag and jewelry by Cartier and Jennifer Meyer.Click to Buy the Look 14 of 23 Halle Berry Flynet Halle Berry looked cool in oversize shades as she went furniture shopping with beau Gabriel Aubry in L.A. The actress stayed true to her usual casual-yet-hip style by wearing an oversize top, leggings and ballet flats.Click to Buy the Look 15 of 23 Kerry Washington Doug Peters/Retna Kerry Washington gave the crowd a breathtaking view of her ethereal Marchesa dress at the London première of The Last King of Scotland. Her long romantic waves and drop earrings by Cathy Waterman accentuated her alluring look.Click to Buy the Look 16 of 23 Shakira Frank Micelotta/Getty Shakira brought a red-hot flavor to the MTV Video Music Awards Latin America with her slinky, bejeweled gown by Roberto Cavalli. The sultry singer's night proved to be as winning as her look-she brought home the Song of the Year award for "Hips Don't Lie."Click to Buy the Look 17 of 23 Shakira Frank Micelotta/Getty Shakira brought a red-hot flavor to the MTV Video Music Awards Latin America with her slinky, bejeweled gown by Roberto Cavalli. The sultry singer's night proved to be as winning as her look-she brought home the Song of the Year award for "Hips Don't Lie."Click to Buy the Look 18 of 23 Diane Kruger Eric Ryan/Getty Diane Kruger showed off her unique style in a not-so-basic brown dress with ornate detail by Chanel. The actress attended the Van Cleef & Arpels party at the Tuileries Gardens in Paris, a fitting location for this floral frock.Click to Buy the Look 19 of 23 Jennifer Garner Vince Flores/Celebrity Jennifer Garner took the plunge at the Hollywood Film Festival's 10th Annual Hollywood Awards in a Grecian-inspired chocolate-colored gown by Gucci. The actress fittingly accentuated the goddess look with gold accessories.Click to Buy the Look 20 of 23 Angie Harmon Donato Sardella/WireImage Angie Harmon dared to be different in this fashion-forward dress by Christian Dior. The actress attended the Dior 2007 Cruise fashion show, held at the brand's Beverly Hills store.Click to Buy the Look 21 of 23 Sienna Miller Kristin Callahan/AcePixs Sienna Miller showed off her gorgeous gams in an ivory cocktail dress by Marchesa at the designer's second-anniversary dinner at Bergdorf Goodman in New York. Her black peep-toe pumps and shoulder-grazing earrings added a modern twist to her elegant mini.Click to Buy the Look 22 of 23 Gwyneth Paltrow Henry Lamb/BEImages A very statuesque Gwyneth Paltrow took on Gotham City in a vintage Yves Saint Laurent dress. The actress, who was attending the Fashion Group International's 23rd annual Night of Stars, wore fire-engine-red lipstick that popped as brightly as the cameras behind her.Click to Buy the Look 23 of 23 Halle Berry Matt Baron/BEImages Halle Berry was the glittering golden girl at the Mercedes-Benz 17th Carousel of Hope Ball in Beverly Hills. The actress wore a shimmery Elie Saab dress, accessorized with a Jimmy Choo clutch and Gunmetal by Spaulding & Gublo shoes.Click to Buy the Look