Thursday, August 20, 2009

How Andy Samberg ended up dressing women (photo)

Every Thursday afternoon, I experience the same Groundhog Day conversation with the girls in my fashion department. They start to debate their weekend date wardrobes and, inevitably, this yammer yields a familiar dialogue:

Fashion Girl: OMG, I’m freaking out. I’ve got nothing to wear tomorrow, and it’s my first date with this guy.

JZ: What’s wrong with what you’re wearing?

FG: This??? I can’t wear Marni on a first date. It has to be something sexy…but chill…easy…but hot!

JZ: You work in fashion—you should look the part.

FG: I work in fashion. I don’t want him to think I’m obsessed with fashion.

JZ: What does that mean?

FG: 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. No, I’ll just wear my little black dress again.

Then my aha moment: I have come to realize that all women basically have two wardrobes—one to wear for other women (and themselves!) and one to wear for men. What works at brunch with girlfriends might not yield you that second date. It’s a simple fact: He’s Just Not That Into Your Skirt.

To the women in my office, I am this wise old fashion sage, constantly offering advice on what to wear and how to wear it. But when it comes to knowing what a real guy wants, how should I know? Sure, I’m a guy, but—and this is their theory—I’m a Fashion Guy. I’m the guy who goes shopping with you, not the guy who thinks Proenza Schouler is a retirement plan. A male friend—okay, he’s a total dude—told me recently that men love contradiction. They want a woman in heels, but not high-maintenance; hot, but still presentable to Mom; able to swig a beer at a baseball game, but turning heads while doing it.

Okay, point taken. But does this really mean that my POV is insignificant when compared to that of the guy next door?

So I decided to solicit the help of a guy next door—actually, three blocks away at 30 Rock—Saturday Night Live’s Andy Samberg. Andy is the perfect foil for me: laid-back, effortlessly hip, a hit with the ladies, and knows exactly what he likes, style-wise (including telling his publicist many times that her shoes were “bitchin’ ”).

And it was on: the Fashion Guy vs. the Funny, Cool Guy. I know my Dolce. He’s got “D*** in a Box.” I speak Lanvin. He raps “Lazy Sunday.”

I invited Andy, who is one of the voices behind this month’s animated film Cloudy With a Chance of Meatballs, to spend the day with me, style-plotting his way through various looks. We dressed some of the ELLE editors for certain situations where a dude’s opinion matters to see how our styling contrasted. When I initially told the girls that we were both going to come up with looks that are chic and relevant to different dating scenarios, they chuckled (at me) and swooned (over him). But judge for yourself. Personally, I admit Andy did great. And I wasn’t so bad either.


Go here to see who we think won:

I like Andy's purse better!!!


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