How to help a guy who wants to look dapper

Hi ESB,

I have a friend who has historically not been very *into* fashion. Or clothing beyond jeans and a t-shirt (bonus points if it references Transformers, TMNT or X-Men). Recently, however, he's begun to get a little more comfortable in his skin and experimenting with clothes and he is debuting somewhat of a new look at a wedding of a mutual friend. Now normally I'd say "Who gives an eff what you wear to someone else's wedding? You're a guest" but I really want him to feel like he looks f*cking awesome for once. The way that only new clothes can make you feel. The way that boys so rarely get to feel when they're stuffed into uncomfortable suits. So the question is: He's bought a yellow and blue plaid bow tie and literally talked about nothing else for the past two weeks. He wants to marry it with a casual fedora and sport coat for a sort of Jason Mraz meets Dr. Who look. How does one pull this off without looking like Christopher Lloyd in "Back to the Future?"

Thanks,

M

P.S. Back story. This kid's been in the closet a LONG time. He's a huge Ghostbusters & Ninja Turtles nerd (and my husband's best friend). It's kind of a HUGE deal for him to care about this. Like the bow tie is his way of coming out without actually saying the words. If that makes sense...

*****

Dude is jumping straight into the deep end here.

The best advice I can give him/you is to MAKE SURE EVERYTHING FITS. Guys who live in jeans and t-shirts always buy their dress clothes too big.

Photo of MGMT (a couple of guys who rarely wear shirts, let alone suits) by Richard Burbridge courtesy of GQ.