Lifestyle Style Fashion Faceoff Sometimes, stylish star minds think alike. You decide: Who wears it better? By Alex Apatoff Alex Apatoff Instagram Twitter Alex Apatoff is the Executive Editor of PEOPLE Digital. She has been with the brand for more than a decade, holding various roles on the Style and Beauty team before becoming the site's Lifestyle Director to coordinate the work across the commerce, evergreen, features and marketing teams. Prior to her role at PEOPLE, Alex worked at Us Weekly (where, among other things, she oversaw the Fashion Police pages) and graduated from Northwestern University with a Bachelors in Journalism. People Editorial Guidelines Published on April 24, 2012 09:45 PM Share Tweet Pin Email Trending Videos 01 of 51 ASHLEY VS. ANNALYNNE Katy Winn/Getty; Jason LaVeris/FilmMagic The Twilight keeps her Stop Staring dress simple with red lips and striped pumps in Beverly Hills, while the 90210 star adds Mary Janes, a hat and a belt in West Hollywood. 02 of 51 MIRANDA VS. KRISTEN INF (2) The model wears her Balenciaga by Nicolas Ghesquiere quilted leather jacket with a maxi and luxe tote in N.Y.C., while the chooses gray skinnies and lace-ups in Paris. 03 of 51 MEGAN VS. EMMA X17online; National Photo Group Megan revives flares by topping her Frankie B. carpenter jeans with a plaid top and fur-trimmed jacket at a Lakers game, while Emma keeps hers retro-cool in two-tone stripes and wedges in L.A. 04 of 51 KALEY VS. ASHLEY Chris Delmas/Visual Press; Byron Purvis/AdMedia/Sipa Kaley wears a short blush Maria Lucia Hohan’s gown with stacked pumps in Beverly Hills, while Ashley opts for floor-length garnet and minimal accessories in West Hollywood. 05 of 51 SHAILENE VS. JESSICA Steve Granitz/Wireimage; Jordan Strauss/Wireimage Shailene wears her Katharine Kidd mini with black pumps and a silver clutch to an Oscars event in L.A., while Jessica goes for monochromatic accents at another L.A. party. 06 of 51 FERGIE VS. LINDSAY AKM Images; Clint Spaulding/PatrickMcMullan.com/Sipa styles her 3.1 Phillip Lim studded sweater with slim dark denim and sandals at LAX, while opts for knee-high boots and a seafoam bag in L.A. 07 of 51 ANNE VS. CHELSEA Bauer-Griffin; APEGA/Abaca The keeps her Elizabeth and James dress casual with sandals and sunnies at LAX, while the TV host dresses hers up with two-tone pumps at a Hollywood premiere. 08 of 51 NICKY VS. AMY Desiree Navarro/Getty; Stefanie Keenan/Wireimage The Charles Henry mini feels simple and chic on the socialite (styled with a tank and booties) in N.Y.C., but the actress gives it a dose of funk with a fringed top in L.A. 09 of 51 JESSICA VS. KATE Freddie Baez/Startraks; X17online wears her Autumn Cashmere cardigan with a paisley dress and booties in N.Y.C., while dresses hers down with shearling boots in Santa Monica, Calif. 10 of 51 AMBER VS. JENNY Michael Tullberg/Getty; INF At the same West Hollywood event, Amber puts a ladylike spin on a pair of Dylan George’s leggings with a tweed jacket, while Jenny goes trendy with a draped blazer. 11 of 51 RACHEL VS. ROSIE John Shearer/WireImage; National Photo Group The paired her Vanessa Bruno blazer with a sweet hat and an oversized clutch in L.A.; in the same city, the model gave hers urban edge with a tee and booties. 12 of 51 MIRANDA VS. RIHANNA Bauer-Griffin; KCSPresse/Splash News Online The supermodel pairs her Nobody “Cult Skinny” jeans with nautical accents in Sydney, while the glams up hers with boots and a fur-trimmed jacket in Paris. 13 of 51 MOLLY VS. KIM Donato Sardella/Wireimage; David Tingey/Splash News Online The mom-to-be wears her A.L.C. tunic belted over pants in West Hollywood, and in Las Vegas the cinches hers at the waist and adds espadrilles. 14 of 51 JENA VS. CHANEL Benkey/AFF-USA; Billy Farrell/BFAnyc/Sipa The actress wears a Cushnie et Ochs frock with metallic sandals and a baby-blue clutch in Hollywood, while the model accessorizes hers with studded pumps in N.Y.C. 15 of 51 MINKA VS. EMMANUELLE Fern/Splash News Online; Kevan Brooks/AdMedia Two L.A. looks on two brunettes: Minka dresses down her Express top with sweats and a bright bag, and Emmanuelle makes it event-worthy with scarlet pumps and pout. 16 of 51 JAMIE VS. PINK JD Pht Bx & MCGM/Splash News Online; GSI The actress rocks her Lanston maxi with flat sandals to shop in Beverly Hills, and Pink tops hers with a hat and long chain necklace to lunch with her daughter in Malibu. 17 of 51 DIEM VS. ALI Jordan Strauss/Getty; Landov Reality-show showdown! The Real World star pairs her Ted Baker mini with peep-toes and a black bag; also in Hollywood, the Bachelorette adds a cobalt clutch and pumps. 18 of 51 ALESSANDRA VS. VANESSA AKM-GSI; INF These ladies know maxis are the hot uniform of mamas and moms-to-be! The new mom wears her Gypsy05 maxi with a tasseled leather jacket in Brentwood, Calif., and the adds a chain-strap bag to hers in L.A. 19 of 51 ROSE VS. ESTELLA Fapian/Zodiac/Splash News Online; Albert Michael/Startraks Rose struts in her Yoana Baraschi minidress, plus tights and booties in West Hollywood, but Estella accessorizes the frock with fold-over boots and a quilted bag in L.A. 20 of 51 AUDRINA VS. MARIA Vladimir Labissiere/Splash News Online; X17online The reality star tucks her Colorfast top into high-waist shorts and adds sandals in Beverly Hills, while the TV host wears hers as workout gear with sneaks and capris in L.A. 21 of 51 KYLIE VS. EMMY Storms Media Group; Rob Kim/Landov The singer clasps her Yves Saint Laurent azure gown at the waist in London, while the actress accents her fuchsia one with a choker and jeweled sandals in N.Y.C. 22 of 51 KATE VS. ALICIA Mark Cuthbert/UK Press/Abaca; Larry Busacca/Getty The wears a full Alexander McQueen ensemble across the pond, while the pairs the nautical top with pants and peep-toes in Beverly Hills. 23 of 51 KOURTNEY VS. NICKY Ramey; AKM-GSI The wears a Splendid top with an oversize tote and chunky boots in L.A., and in Beverly Hills, the designer accents the piece with a chain-link bag and flats. 24 of 51 DAKOTA VS. SAMI Richie Buxo/Splash News Online; Charles Eshelman/Filmmagic ’s Miu Miu cape covers her silvery mini and nude pumps at an N.Y.C. event; in the same city, Sami wears the topper with a beaded necklace and checkered pumps. 25 of 51 BROOKE VS. JAMIE Everett Collection/Rex USA; London Ent/Splash News Online The TV host dons her cutout Guess by Marciano sheath with ankle-strap peep-toes in Las Vegas, while the actress adds a Linea Pelle clutch at a Beverly Hills event. 26 of 51 AMANDA VS. KATY National Photo Group; 310pix The actress wears her AllSaints “Walker” jacket with beat-up boots and leggings in L.A., and in London, the goes bad-ass in leather pants and square shades. 27 of 51 DAKOTA VS. SARAH JESSICA Hector Vallenilla/Pacific Coast News; Bauer-Griffin looks boho in the Big Apple in Current/Elliott “Beatnik” jeans and slouchy accessories; also in N.Y.C., wears a tailored moto jacket and ballet flats. 28 of 51 ANN VS. EMMY Erik Pendzich/Rex USA; Lloyd Bishop/NBC/AP The Today anchor glows in chartreuse Michael Kors and a python clutch in N.Y.C., while the actress takes Manhattan in the same dress and ankle-strap pumps. 29 of 51 CIARA VS. STEFANIA EM43/Splash News Online; Media Punch The singer dons her striped Line sweater with jeans and aviators in L.A., while the Carrie Diaries actress plays up the hippie vibe with fringed boots and layered tees in N.Y.C. 30 of 51 LANA VS. VANESSA David Tonnessen/Pacific Coast News; Anthony/AD/Pacific Coast News The pop star wears her striped Ella Moss maxi with flats in West Hollywood, and in L.A., the dresses hers up with wedges and hoops. 31 of 51 DIANNA VS. REESE Dominique Charriau/Wireimage; AKM-GSI Media The Glee star wears head-to-toe Louis Vuitton in a muted palette in Paris, and the chooses the same frock in a sunny shade in Rio de Janeiro. 32 of 51 NIKKI VS. ELIZABETH Taylor Hill/Filmmagic; Ramey Twilight actress dons a Philosophy di Alberta Ferretti coat with slinky sandals in N.Y.C., while the Olsen sis gives hers a retro vibe with a red hat and brown cords in L.A. 33 of 51 CARMEN VS. EMMY Eric Charbonneau/Wireimage; Jordan Strauss/Wireimage Carmen spices up her ivory Ted Baker peplum sheath with golden accents in L.A., and in Santa Monica, Emmy picks monochromatic accessories for her black version. 34 of 51 CHARLIZE VS. ASHLEY Bauer-Griffin; AKM Images A Chaser tee looks casual on the with skinnies and a fedora at LAX, and funky on the , who adds supershort shorts and chunky boots in L.A. 35 of 51 FELICITY VS. AHNA Matt Sayles/AP; Andreas Branch/PatrickMcMullan.com/Sipa Stanley Tucci’s bride-to-be wears Nanette Lepore with neon platforms in L.A., a look almost as bright as the actress’s ensemble, featuring white pumps, in Beverly Hills.Vote on More Fashion Faceoffs > 36 of 51 TARAJI VS. MIRANDA Tsuni/Gamma; Richard Brian/Landov Gilded gals! The actress wears shimmering Randi Rahm with an oversized clutch in L.A., and the chooses golden jewels and soft curls in Las Vegas. 37 of 51 OLIVIA VS. KATE Sara De Boer/Startraks; Dave Allocca/Startraks The actress wears Louis Vuitton with metallic details and an updo in L.A. The Sports Illustrated swimsuit model goes for bombshell waves and pointed pumps in N.Y.C. 38 of 51 TORI VS. MEGAN Courtesy Kohl's Even celebs love a bargain: teams her floral high-low LC Lauren Conrad dress (only $50 and found ) with a cuff, while Megan opts for nude platform pumps, both in L.A. 39 of 51 VANESSA VS. TIA Jen Lowery/Splash News Online; Dimitrios Kambouris/Style/NBCU/Getty One cool blazer, two hot colors! The tops a patterned maxi with a cobalt Kate Frances in Hollywood, and the actress pairs the red version with bright jeans in N.Y.C. 40 of 51 KELLY VS. OLIVIA Joe Schildhorn/BFAnyc/Sipa; Stewart Cook/Rex USA The TV host keeps her Big Apple cool in a Gucci gown with a down do and simple accessories, and the actress pairs hers with gold accents in L.A.. 41 of 51 EMMA VS. JENNIFER Jason Merritt/Getty; Lester Cohen/Wireimage These ladies love Lanvin! The wears her designer dress with loose locks and black pumps in West Hollywood, while the adds drama to hers with platforms and a swept-back do in Hollywood. 42 of 51 JENNA VS. MILEY Survivor/Pacific Coast News; X17Online ’s wife teams her Lovers + Friends kimono top with wedges in L.A. keeps the floral topper equally casual with flip-flops and round shades while in Studio City, Calif. 43 of 51 GWYNETH VS. SHALOM Larry Busacca/Getty; Ferdaus Shamim/Wireimage The wears gold-belted Stella McCartney with a sleek pony and rings in L.A., while the supermodel chooses the white-accented version and adds a metallic clutch in London. 44 of 51 BETHENNY VS. MICHELLE Curtis Means/Ace Pictures; Christopher Polk/Wireimage Both the and the actress kick it old school with the same Express denim jacket. Though Bethenny pairs it with a flowy black maxi and floppy hat in N.Y.C., while Michelle hits a Palm Springs bash wearing hers with a printed dress and crossbody bag. 45 of 51 CHRISTINA VS. KIM Lewis Jacobs/NBC; Jordan Strauss/Wireimage Both flaunting their curves in an orange Roland Mouret number, The Voice’s adds glam pumps on the show’s set, and pairs it with strappy sandals in L.A. 46 of 51 KOURTNEY VS. JAMIE Said Elatab/Splash News Online; National Photo Group The wears her Paul & Joe dress buttoned up with girlie accents in N.Y.C., and in Beverly Hills, the actress leaves hers slightly open with a blue belt. 47 of 51 BROOKLYN VS. EMILY Alberto E. Rodriguez/Getty; Rex USA Brooklyn keeps her Diane von Furstenberg shift classic with red pumps at a West Hollywood event, while Emily gets edgy with with neon sandals in Beverly Hills. 48 of 51 SELMA VS. EVA Isaac V/Broadimage; AKM-GSI One Splendid top, two splendid L.A. looks! Selma dons hers with boyfriend jeans and colorful accents, and makes it night-out-worthy with white denim and sandals. 49 of 51 ELIZABETH VS. JADA Charles Eshelman/Filmmagic; Eduardo Parra/Wireimage The Hunger Games star wears studded Versace with tights and booties in N.Y.C., while the Hawthorne actress works the lime version with bronze sandals in Madrid. 50 of 51 KATIE VS. DAKOTA National Photo Group; X17online styles her Current/Elliott with heels and a button-down in Hollywood, while opts for lots of pink in N.Y.C. 51 of 51 GWYNETH VS. EMMA Pacific Coast News; StarFeine.com/Splash News Online Alternative Apparel top gets layered under a moto jacket and pendants in N.Y.C.; also in town, wears hers simply, with cuffed denim shorts and flats.