Lifestyle Style They Wore What? Stars' Most Outrageous Shoes From "can you walk in those?" to "why would you want to?" – Hollywood keeps stepping out in puzzling and truly over-the-top footwear. By Melissa Liebling-Goldberg By People Staff Published on November 25, 2008 10:00 PM Share Tweet Pin Email Trending Videos 01 of 28 VICTORIA BECKHAM GG/Flynet; Roger Wong/INF (inset) Forget high heels – what about no heels? The British star defies gravity in her molded, heel-less Antonio Berardi boots while launching her perfume in N.Y.C. 02 of 28 MARY-KATE OLSEN Sara Jaye Weiss/Startraks Photo The star designer picks a straight-off-the-runway look with her multi-strapped, knee-high Givenchy by Ricardo Tisci gladiator sandals. 03 of 28 RIHANNA Fame The singer played the part of a Good Girl Gone Bad in her elaborate woven Balenciaga gladiator boots while shopping in L.A. 04 of 28 GWYNETH PALTROW Fame; Insidefoto/PR Photos (inset) The Iron Man star got tongues wagging this summer with her super-short hemlines and extra tall heels. For the Rome photo call, the actress paired her Preen mini with Dsquared heels that clock in at almost 6 inches high! 05 of 28 MADONNA Kevin Mazur/WireImage The singer’s ultimate weapon these days are her pistol-heeled Chanel pumps that she wore to her directorial debut in N.Y.C. 06 of 28 LINDSAY LOHAN GM/FT/Flynet The actress gets a leg up in her short-shorts and woven Balenciaga gladiator booties with spike metal heels. 07 of 28 JENNIFER CONNELLY Jeffrey Mayer/WireImage Never one to shy away from tough fashion choices, the Reservation Road star set tongues wagging with her braided black and white Balenciaga sandals at the film’s Los Angeles premiere. 08 of 28 LILY ALLEN Goff/INF; Alpha/Landov (inset) Why choose between stilettos and platform wedges when you can have both? The singer struts in her two-in-one Louis Vuitton satin platform heels. 09 of 28 JULIANNE MOORE Fame FitFlops were a huge hit this summer, but what’s a fashionista to do with sensible footwear? The company created a special pair of luxe gladiator sandals that lace over the ankle for $165 – and which found their way onto the actress’s feet. 10 of 28 EVA LONGORIA John Hopkins/BuzzFoto The petite star adds five inches to her height in her painted YSL platforms while shopping in L.A. 11 of 28 NICOLE RICHIE SS/Flynet; courtesy Balenciaga.com The new mom hasn’t lost her style edge, adding braided Balenciaga sandal-booties with metal heels to her skinny jeans. 12 of 28 MARY-KATE OLSEN Rodrigo Marques/Splash News Online Leave it to the cutting-edge star to take the gladiator sandal trend to new heights with these knee-high Chanels. 13 of 28 ASHLEY OLSEN Fame Call it two of a kind – Mary-Kate’s sister showed off her own over-the-calf Azzedine Alaia gladiator sandals at an event in August. 14 of 28 LINDSAY LOHAN Pacific Coast News Always up for trying out the latest trend, the star trotted out in open-toed ankle booties at a salon opening in Los Angeles in the spring. 15 of 28 JESSICA ALBA Lalo Yasky/WireImage Usually one for classic style choices, the Good Luck Chuck star tied on these dominatrix-inspired Versace platforms at a Madrid photocall in July. 16 of 28 BEYONCé Johns/Maryannakis/Splash News Online The singer took on a punk edge with her studded DSquared boots while dining out in N.Y.C. in October. 17 of 28 MISCHA BARTON Humberto Carreno/Startraks Perhaps taking “moon boots” a little too literally, the actress hit the streets of Manhattan in celestial vintage boots in April. 18 of 28 SARAH JESSICA PARKER Carrie’s rosettes made a comeback when the Sex and the City star showed off these flower-bedecked Alexander McQueen heels in March. 19 of 28 HEATHER GRAHAM: MISS Lisa Rose/JPI Graham herself referred to her sky-high, metallic Versace platforms as “stripper shoes.” We’re still not sure how the 2007 nominee (for Bobby) managed to make it down the red carpet! 20 of 28 NICOLE SCHERZINGER Michael Loccisano/FilmMagic The Pussycat Dolls frontwoman rocked out in her studded Christian Louboutin ankle boots at TRL in August. 21 of 28 MARIAH CAREY Neill J. Schutzer/Ramey Always one to add extra sex appeal to any outfit, the singer headed to dinner in L.A. in five-and-a-half inch Giambattista Valli platform sandals. 22 of 28 PARIS HILTON Flynet The heiress mixed multiple bold patterns, pairing her striped Christian Louboutin pumps with a zig-zag Nieves Lavi wrap dress while shopping in L.A. in September. 23 of 28 ANGIE HARMON John Shearer/WireImage;Vince Flores/Celebrity Photo The actress blooms in sculpted floral Prada heels at a party for the brand. 24 of 28 FERGIE Scott Doctor / Splash News; MJT/AdMedia The singer gets G-L-A-M-O-R-O-U-S in her head-to-toe Dolce & Gabbana for her birthday – check out those harlequin snakeskin peep-toe booties! 25 of 28 JENNIFER CONNELLY Jeffrey Mayer/WireImage Never one to shy away from tough fashion choices, the Reservation Road star set tongues wagging with her braided black and white Balenciaga sandals at the film’s Los Angeles premiere. 26 of 28 BEYONCé Frank Micelotta/AMA/Getty The singer showed off her vocal prowess and went Rainbow Brite in her athletic-inspired Balenciaga sandals at the American Music Awards. 27 of 28 JESSICA BIEL INF The star needed help walking into designer Giambattista Valli’s February fashion show in his jaw-dropping six-inch platform heels. 28 of 28 MICHELLE TRACHTENBERG Richie Buxo / Splash News; courtesy Saksfifthavenue.com The Gossip Girl star gives us plenty to whisper about in her surrealist Marc Jacobs heels.