Andy Samberg Takes On “Elle” Fashion Challenge For “Date Looks”

Over at Elle, Creative Director and Fashionisto Joe Zee has had an epiphany. Complains a fashion editor to Zee, “He won’t understand that it’s all about my new draped devore velvet Balenciaga dress right now. He’ll only think I’m wearing curtains,” as she laments (oh boo hoo) her first-date outfit choices. And then it hits Zee: Women dress differently for guys than they do for girls. You don’t say? It may have taken Zee a while to figure this out but he gets it now, explaining, “It’s a simple fact: He’s Just Not That Into Your Skirt.”

And so Zee enlists hot man Andy Samberg to face-off in a fashion duel of “date looks” to see if Elle editors prefer Zee’s conceptual high-fashion stylings, or if they vote for Mr. Dick in a Box’s horndog looks. The results? Both hilarious and surprising!

In scenario #1, a “night out,” Zee dresses an Elle editor in a slightly ’80s dress with power ankle booties and a chignon. Andy’s look goes for hair down (so obviously a guy move) and a sexy gold cocktail dress. She prefers Zee’s.

We’re surprised that Andy took the challenge so earnestly, as we were expecting him to come up with some horribly embarrassing and clichéd outfits. For “meeting the parents,” we definitely give him the winning point when Zee dresses another editor in an unflattering “Golden Girls“-chic dress, while Samberg goes for the simple girl-next-door peasant dress. Andy’s advice: “Always err on the side of ‘nice’ with the parents. I mean, you don’t want them to think you’re a dud, but no one ever came back from that experience like, ‘I shoulda went sluttier.’ (Note: This does not apply for dudes. If there’s one thing I’ve learned, it’s that dads love a boyfriend in a midriff tee.)”

The other scenarios include clubbing, dressing for success, chilling on the weekend, and having a first date. May we be so bold as to suggest that Andy Samberg start a fashion blog for women? He’s maybe missed his second calling! [Elle]