It’s not uncommon for friends to come to me for style advice. That’s fine by me, as long as you’re asking on your own behalf. Things get a little more complicated when I’m asked to upgrade an unsuspecting boyfriend’s style game — whether he likes it or not.
Truth be told, there’s not much I can do in that case. Or will do. I’m a big believer in wearing whatever makes you feel confident, and I disagree that any style (or lack thereof) is somehow intrinsically incorrect. Sure, there are some things any guy can wear to present himself better, but ultimately, that’s a choice I leave up to the guy himself. It’s not fair to try to change something as fundamental to a person’s identity as how he dresses.
Having been recruited as many a couple’s unwilling arbiter back in my retail days, I can tell you one thing with confidence: no matter how well-meaning, forcing a style change on him will only make him push back against your efforts. As soon as I was tasked with a manly make-over, I knew the only way to secure a sale and make the guy happy was to see what he thought about the whole situation. Cue tuning out the ladyfriend. “Dude, what do you want to wear?” This carries over into writing about menswear. Guys need to be talked to, not talked down to, and the good mags get that.
It’s hard for guys to change how they dress, because many of them don’t have a large vocabulary when it comes to clothes. It gets even harder to talk about it when they feel pressured by someone they trust. However, they do know what looks cool to them. They know if they want to look like friggin’ Ryan Gosling in Drive, or Don Draper from Mad Men. Your boyfriend may feel a little self-conscious actively attempting to change his look, so the best thing you can do for your boyfriend is to start a dialogue to help him out.
Listen to him. Ask him what he wants to try on, what he wants to keep doing and what he wishes he could pull off. Give him time to find inspiration, and point him in the right direction if he needs it. Above all, however, let him dictate the transformation — not least whether he wants to undertake it.
On the off chance that he wants to go all James Dean but thinks he lacks the cool factor for a leather jacket, start by taking small steps. A pair of shit-kicking boots will do nicely at first, then maybe a nicely-fitting pair of dry denim jeans that make him feel comfortable. If he wants to go for a more sophisticated look, a blazer that he can wear everywhere is a great place to start. Get it tailored so he feels like even more of a boss.
Once he feels comfortable in the direction he’s heading in, he’ll take it from there.