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.