Gallery: Looks That Are Hard to Pull Off

Last week, I was thinking about suits: namely, when it works, it’s awesome, when it fails, it really fails. So today I’ve compiled some photos of other pieces that present real challenges: high-waisted denim, harem pants, midriff-bearing 90′s looks and more. I wouldn’t say that anything here can be categorized as “always terrible” (capes are often awesome and functional!) but I would say most of them qualify as “hard to pull off” (as the title suggests–). So, what works here and what doesn’t is up to you. Moreover, what’d I leave out?

Ed. Note: For more difficult pieces and challenging styles, here’s Part II.

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    • bodo

      who is “she”?

      • Ashley Cardiff

        Chloe Sevigny, awesome but near-impossible to imitate.

    • Lindsay Cross

      I have an issue with ultra-girly florals. Some women can still look trendy and cute in them, I feel like I’m trying to match my toddler.

    • Teenie

      i disagree on the maxi dress – i’ve become a huge fan of them, and i’m short. i’m also pretty thin, which i think is probably more likely to be the defining factor on whether the dress looks good or not. but it actually makes me look taller and leggier than normal.

    • Lee

      I think Fergie was the only one making her look work here. The one in the maxi dress (Eva Mendes?) wasn’t bad, although it’s kind of a maternity-dress look.

    • b

      This was rather interesting, save for the perpetually expanding and extremely annoying macy’s and smart water ads that kept expanding themselves while trying to view the slideshow. I don’t fucking care if Jennifer Aniston drinks smart water, in fact, consumption of bottled water is super irresponsible and causes a ridiculous amount of waste and the people who swear by it are contributing boat loads of unnecessary trash to our landfills. Thanks for crapping all over our planet with your aversion to tap water, Aniston, and thanks for making me want to punch my laptop with these oppressively obnoxious, in your face, post ruining advertisements.

      • heavy snatch

        If you use Firefox, there’s an extension called Adblock Plus that removes all ads from the internet. It’s great.