Boy Problems: Our Struggles With Menswear

Maybe we're fashion retards, but we just don't get contemporary menswear. Because "real men" — that is, straight, beer-drinking, X-Box-owning, porn-watching men — are never going to wear skinny suits with cropped legs. But what we don't get more than contemporary menswear is today's lead story in The New York Times Thursday Styles section on the just-concluded contemporary menswear shows in Milan. We aren't Robin Givhan, but we're pretty sure this story was fashion criticism at its most all-over-the-place, with references to everything from hedge fund hotties to late 80's gender theory to dandyism to Pete Doherty. Oh, and somehow Prada and Romanticism got tossed in there too! We like to think of ourselves as fairly-bright women. But this one left us baffled. But then, we thought, perhaps we're not being fair! Maybe it's because we're not guys (like Times writer Guy Trebay) and maybe we need penises to have an opinion on menswear? Or even find it interesting? Looking for a few good answers, we had Jen chat up friend-of-Jezebel and quintessential straight dude Don. Their IM deliberation on pink silk pajamas — and the allure of a woman wearing man's clothes — after the jump.

JG: So today's NYT Styles section has this article on "innovative' menswear. Like, would you wear a skinny suit with a cropped ankle?
Don: "Innovative" is pretty much the word that gives your assertion credence.
JG: Indeed. So was my suspicion.
Don: This is great stuff.
JG: Like, would you rock that?
Don: Hahahahahha.
JG: It's not even esoteric. You know how you can rationalize absurd women's fashion with some overly-academic art historical-sociological explanation? You can't with this. This is a skinny checked suit. And no dude goes out looking to get laid — by a girl — wearing that.
Don: Okay, well, I like to not be harassed by people. That suit would definitely get a lot of "faggots" from strangers wearing that.
JG: Really, the sweater vest underneath the suit takes it to a whole other level. Like, you still might be safe without that.
Don: No, no you wouldn't. I don't know where you hang-out, but my favorite bar downtown has a lot of Cubs t-shirts. I feel weird walking in with a polo.
JG: Okay so even a gay man wouldn't wear that suit with a sweater vest?
Don: This one is probably worse...
JG: That's my thing with menswear! What purpose is it serving? No guy with an X-Box (or better, a Wii) will ever wear that. And it's never going to trickle down in some watered-down, derivative version, even.
Don: No, not at all.
JG: Guys who like beer, boobs, and video games are not going to adapt to that.
Don: I dream of a day when business attire is a jumpsuit. That way, I know exactly what I have to wear and only focus on the cleanliness of my underwear. Function is key. I would wear this. If I was going to a Halloween party. As Jarvis Cocker. But this could be a return to Rat Pack, no?
JG: Do you want to return to the Rat Pack?
Don: No. But I can see how it can appeal to certain men.
JG: What did you wear to work today?
Don: Taking the day off - KnivesOut t-shirt, jeans, and ghetto slippers.
JG: I think that is what every straight dude I know is prob wearing. Okay, my last menswear question is this — did you read the article I sent you? All that talk of pink silk pajamas? What would it take to get you into pink silk pajamas?
Don: Ohhhh no. I didn't read it, went straight for the pictures, like porn. I mean, looking at clothes and scoffing is far less painful than reading about clothes you really don't care about. But... I did want to make one point. The jeans/t-shirt/fuck it attitude does carry over to women as well.
JG: In what way?
Don: I was talking to some folks the other night about all that Victoria's Secret shit...
JG: Victoria's Secret is gross.
Don: But every now and then it's nice, kinda like role-playing with clothing. Okay , so I was talking to these 2 guys and 2 girls, like I was saying...
JG: Okay and what did they conclude?
Don: Well, it was more...heyyyy, favorite shit to see a girl in. And really, both dudes agreed it was when they use our button-downs in the morning. Of course, I'm partial to union-jack suits or underwear and an NHL jersey (and I don't even like hockey).
JG: But you don't like that because it's some profound sartorial statement — it's because it's nice to see a girl wearing your clothes the next morning.
Don: Ummmmm, maybe. It's also... holy shit, girls really are smaller than dudes.
My shirt can be a dress on my most women. (Unlike menswear!) But yeah, suits... I'm going to the Men's Wearhouse. And I'm not spending more than $500... maybe $600 if the shit's banging. I've had my one 5 hunny suit for a good 8 years. I have a thrift suit (30 bucks), but that shit needs some serious help. And I bought a suit for $150 because I was young and thought "Dude, Elvis Costello would totally wear this" — It's not that cool now. Yeah, suits are things you have to buy (funerals, weddings). I really think about a new bicycle, HDTV and the lust for tools (but since I don't own, it would be stupid, but damnnnnn I WANT IT). So right, that checkered suit, fuck that. Also, if we're going to boil it down... who's going to fuck you in that suit? You don't want to fuck that person!

Looking Like a Billion Bucks [NYT]