It’s time to play Hip or Homeless? with some of the looks from the Alexander Wang Spring 2011 lookbook, where we determine if a look is hip (good job, Alex!) or homeless (ouch). We all love Alexander Wang, of course, but you know that some of his looks walk the fine line between casual and homeless. They bypass hanging-out-at-home sweats straight to the street, literally. (Disclaimer: I’m not making fun of the homeless. Homelessness is serious, but so is the problem of rags posing as designer fashion.) With that said, let’s play!

Hip: Perf for running to the bodega or hanging out at dog park.

Homeless: Grandpa sweater over grandma’s house dress.

Homeless: Three words — sweats under skirt.

Hip: Luxurious fabric, relaxed, but not oversized and all buttons intact!

Homeless: What’s happening with the sleeves?

Homeless: Can we scrunch anything else?

Hip: Great proportions and well-fitting.

Hip: DIT-TO!

Homeless: Frumpedy-frump!

Hip: Great formfitting silhouette and zipper detail.

Homeless: What the eff is that flap thing at the back?

Hip: Silky charcoal skirt + Relaxed tunic with pushed-up sleeves = winning.

Homeless: No waist, no shape, no good.

Hip: Not your nana’s bridge-playing leisure suit!

Homeless: Grandpa cardi, dress and sweats (another sweats-under-dress combo! Why, God, why?)

Homeless: How many layers are there here, exactly?

 Out of the looks we examined, it’s Homeless for the win with nine versus Hip’s seven! Better luck next collection, Alex!