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Madonna and Ashlee Simpson Wear Chanel Gun Heels

Who Wore It Better? Chanel Pistol Heels

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

Join The Conversation
elzi elzi 7 years
Madonna Ashleys look Is too bohemic, girly and unconserned, this kinky ´lady 007´ style needs to be more reserved
Michaelrcks Michaelrcks 8 years
Madonna, DUH
NurseKimberly NurseKimberly 8 years
greenapplelover greenapplelover 8 years
Would prefer them on Ashlee but I don't care for the rest of her outfit much so... Madonna it is.
oni1 oni1 8 years
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 Karelynn 8 years
They both look cute, but I voted Ashlee.
tulleandtea tulleandtea 8 years
MADONNA! Haters can hate. The shoes were made for her.
Sunflower-Sutra Sunflower-Sutra 8 years
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 redchick152 8 years
i picked madonna b/c NOTHING on ashlee is done "naturally."
iewutia iewutia 8 years
girlgreen girlgreen 8 years
madonna looks good in them, but i like them better with ashlee's outfit.
eriNicole eriNicole 8 years
ashlee's skirt, being shorter, draws more attention to the shoes :D
radioragdoll radioragdoll 8 years
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.
pennylela pennylela 8 years
my vote is for madonna. as usual, ashlee just looks like a carbon copy fallout boy fan. oh wait...
reactionary reactionary 8 years
wow. 138 madonna to 139 ashlee. i've never seen so close of a race before. my vote's on madonna.
Talldiva45 Talldiva45 8 years
I don't like either of their outfits - the shoes are cool though. Neither.
shannydoots shannydoots 8 years
Don't like either, but I have to say Madonna. Ashlee just looks ridiculous to me.
soapbox soapbox 8 years
Madonna. Ashlee looks kind of messy.
SweetFirefly SweetFirefly 8 years
Madonna is waaaaay too old for that. The shoes work on Ashlee because she's still young. Madonna just looks like she's trying too hard to hang onto her youth.
aimeeb aimeeb 8 years
I hate both their outfits and just want the shoes!
SaRaH-22 SaRaH-22 8 years
emalove emalove 8 years
miss-malone miss-malone 8 years
silversnowflake silversnowflake 8 years
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