Lifestyle Style Highflying Style in 2009 See how the stars took fashion to new heights and turned airport jetways into fashion runways this year By People Staff Published on December 29, 2009 05:00 PM Share Tweet Pin Email Trending Videos 01 of 24 JESSICA SIMPSON Brandon Todd/Splash News Online The sunny is summer-ready in her multi-print Elizabeth & James maxidress, white purse and pinned-back locks as she makes her way through the airport in Washington, D.C. 02 of 24 RIHANNA Saleem Elatab-Ahmad Elatab/Splash News Online The sultry in stripes stays tough in her leather cap and jacket paired with patent oxford shoes, Hussein Chalayan for J Brand jeans and ring-filled fingers while leaving JFK. 03 of 24 KIM KARDASHIAN Humberto Carreno/Startraks The grins and bares it in a one-sleeved gray dress and black patent pumps while rolling her coordinating checkered luggage through JFK airport. 04 of 24 JENNIFER ANISTON Flynet Still feeling the warmth of her Mexican getaway, the accents her new tan in a blue T-shirt and boyfriend jeans paired with her favorite Stuart Weitzman espadrilles and a straw fedora in L.A. 05 of 24 BEYONCé Myunggu Han/Abaca The international pops onto the scene in Seoul, South Korea, in a pink face-printed T-shirt, embellished jacket and frayed jean shorts paired with peeptoe platforms, Botkier metallic satchel and neon coral lips. 06 of 24 MILEY CYRUS Ramey She’s a little bit county and a little bit rock ‘n’ roll! shows off her legs in a pair of Frye cowboy boots and short cutoffs layered with a fringe vest, studded hip-slung belt and necklaces and bracelets galore. 07 of 24 BRADLEY COOPER National Photo Group What Hangover? The sexy star looks perfectly put-together for a trip out of LAX in his half-tucked plaid shirt, dark jeans and tousled locks. 08 of 24 MADONNA CMB/Splash News Online Undercover in a sweater hat, checkered scarf, puffy jacket and cuffed jeans, the pop strolls through JFK Airport with daughter Lourdes, who looks equally stylish in a cropped jacket, tunic, lace leggings and glittered slip-on TOMS shoes. 09 of 24 HALLE BERRY National Photo Group They had to have planned it! The Oscar-winning shows off her legs – and her color-coordinated family! – in black leggings and booties underneath her gray coat while strolling through LAX. 10 of 24 PARIS HILTON Insight Celebrity/Flynet Looks like it’s a wild ride for Doug Reinhardt’s who sports leopard from trench to tote for the couple’s arrival at LAX. 11 of 24 KATY PERRY John Parra/WireImage It’s a donut hole for one as the eccentric brings her onstage antics to Miami in a gray sequin-detailed top and comfy pants. 12 of 24 DAVID BECKHAM Gene Young/Splash News Online He even makes flannel look good! The underwear dons a trucker hat and plaid button-down, half-tucked into jeans – just like a regular guy! – for his arrival in Washington, D.C. 13 of 24 DIANE KRUGER Dean/National Photo Group The Inglourious Basterds rolls through LAX in a faded denim romper and white T-shirt topped off with a boyfriend blazer and her favorite fedora. 14 of 24 JENNIFER LOPEZ INF/Splash News Online This of twins gets comfortably chic in a graphic print Diane von Furstenberg maxidress with a rope halter and metallic sandals while toting son Max through the Nice Airport in France. 15 of 24 KHLOE KARDASHIAN Gustavo Caballero/KK/Getty The reality star brings glamour back to travel with her wide-brimmed hat, Louis Vuitton purse, cropped trench coat and platform sandals as she lands at Miami International Airport. 16 of 24 ED WESTWICK Jackson Lee/Splash News Online On the East Coast, Leighton’s onscreen steals some prepster tips from alter ego Chuck Bass, pairing his fitted T-shirt with neatly cuffed jeans, sockless loafers and a nylon Coach bag. 17 of 24 KATIE HOLMES AND TOM CRUISE Ramey What to wear on a scenic helicopter ride in Brazil? ’60s-inspired summer chic! Check out Katie’s patterned headband and yellow dress, Tom’s crisp pale blue polo and Suri’s sweet frock. 18 of 24 VICTORIA BECKHAM Rachpoot/INF The star offsets her sleek military-inspired hat and coat with an ultra-feminine Valentino bag as she makes her way through LAX. 19 of 24 LADY GAGA Splash News Online The singer sticks to her signature out-there fashion sense as she walks through the airport in New Zealand in sliced-up leggings and a sharp-shouldered blazer. 20 of 24 KARL LAGERFELD Splash News Online The legendary Chanel designer shows his sense of humor, along with his impeccable sense of style, with his self-referential tote bag. 21 of 24 GWEN STEFANI National Photo Group The singer, in Current Elliott tie-dye jeans, leads her equally fashionable brood through LAX. 22 of 24 CAMERON DIAZ CHAB/JHAB/ZDS/Wenn It’s all about the luxe accessories – from her Lanvin flats to her Chanel purse to her Burberry checked scarf – as the star lands at London’s Heathrow Airport. 23 of 24 EVA LONGORIA PARKER Matrix/Flynet The actress makes her way to the Cannes Film Festival in a slim ivory jumpsuit and vibrant pink purse. 24 of 24 ANGELINA JOLIE Jun Sato/WireImage With all six kids in tow, Jolie stays cool in her black Akris coat and oversized shades while carrying baby Vivienne Marcheline through the Narita International Airport.