Madonna and Ashlee Simpson Wear Chanel Gun Heels

Who Wore It Better? Chanel Pistol Heels

April 14, 2009

Chanel's pistol heels have made their way onto the feet of a few bold celebrities. The queen of experimentation, Madonna, wore hers back in October with a black Dolce & Gabbana dress. The chiffon fabric of her frock helped downplay the roughness of the heels. Ashlee Simpson also rocked Chanel's pistol heels during a night out in LA. She opted for a more casual approach by wearing a striped tee and black flowy skirt. Both ladies clearly love funky footwear, but who pulled this one off more naturally?

Source and Pacific Coast News Online

37 Comments

elzi 3 years 10 weeks

Madonna Ashleys look Is too bohemic, girly and unconserned, this kinky ´lady 007´ style needs to be more reserved

elzi 3 years 10 weeks

MadonnaAshleys look Is too bohemic, girly and unconserned, this kinky ´lady 007´ style needs to be more reserved

3 years 10 weeks

Madonna! Ashleys look is too bohemic, girly and unconserned, this kinky ´lady 007´ style needs to be more reserved

Michaelrcks 4 years 5 weeks

Madonna, DUH

Michaelrcks 4 years 5 weeks

Madonna, DUH

NurseKimberly 4 years 5 weeks

Madonna

greenapplelover 4 years 5 weeks

Would prefer them on Ashlee but I don't care for the rest of her outfit much so... Madonna it is.

oni1 4 years 5 weeks

neither is my favorite but i like how ashlee's ensemble is a little flapper and a little bonnie and clyde. the shoes bring it all together.

Karelynn 4 years 5 weeks

They both look cute, but I voted Ashlee.

tulleandtea 4 years 5 weeks

MADONNA! Haters can hate. The shoes were made for her.

tulleandtea 4 years 5 weeks

MADONNA!Haters can hate. The shoes were made for her.

Sunflower Sutra 4 years 5 weeks

To be honest, i really don't see anything special about the shoes, regardless of the outfit. Madonna's dress looks like it might have some nice details to it that don't show up on my computer screen, but i can't really tell.

redchick152 4 years 5 weeks

i picked madonna b/c NOTHING on ashlee is done "naturally."

iewutia 4 years 5 weeks

Ashlee

iewutia 4 years 5 weeks

Ashlee

girlgreen 4 years 5 weeks

madonna looks good in them, but i like them better with ashlee's outfit.

eriNicole 4 years 5 weeks

ashlee's skirt, being shorter, draws more attention to the shoes :D

radioragdoll 4 years 5 weeks

i think the race is so close because neither outfit is spectacular; to be honest, i don't think the shoes are that great either. designer does not equal automatically fabulous in my book.