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A Curated Boyfriend

July 15, 2011
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It’s a problem almost every man-dating lady (or man-dating man) faces at one time or another: The Badly Dressed Boyfriend. Sometimes it’s an episodic thing — you’re dressed to the nines and he’s in a wrinkled t-shirt — which can easily be solved with an artfully raised eyebrow that says, “Really? You’re wearing THAT?” But sometimes the problem is bigger.The chronic bad dresser is a difficult nut to crack. Most of the time, they have many redeeming qualities; it’s easy to ignore the Dad Jeans and white Reeboks when you’re staring into his sparkling blue eyes and admiring his adorable dimples.
But when the schmoopy phase of the relationship ends, you realize that something needs to change.Let it be clear — no one can change anyone else. All change happens from within. But sometimes the right lady can be the right change agent for the right man. And if you’re a dude reading this, it’s not that we don’t like the way you look. More, it’s that we’re hopelessly head-over-heels in schmoop with you and we just think the outside needs to more accurately reflect all your awesome internal qualities. And we don’t want you to look like a slob when we show you off to our friends.

Enhancing your man’s wardrobe depends on why that wardrobe needs enhancement. Chances are, he falls into one of three, easy-to-define categories.

  • The “I’m not naked” guy has never given much thought to his clothes, beyond not being naked. He’s probably aware of social cues that dictate what he should wear, so he’s not going to show up in jeans for your cousin’s wedding, but the suit he’s wearing probably doesn’t fit him well and the tie is probably butt ugly. The key to enhancing Not Naked’s wardrobe is lots of positive reinforcement. You know that scene in Gilmore Girls when Lorelai goes to Bloomingdales and buys all kinds of clothes for Luke, telling him they were on sale and she just couldn’t pass them up? Yeah, do that, even if it’s a lie.
  • The stuck in a rut guy hasn’t changed his look and it is now dated or ill-fitting, usually following an extreme weight loss or gain. This is where you need to use a little tough love. With this guy, it’s not that his clothes are bad, but that they’re wrong for him, which can be easier to make over. If he’s still trying to get away with cargo pants and a Nirvana t-shirt at work, it’s OK–nay it’s your responsibility–to say, “Honey, that is not appropriate.” Likewise, if he’s lost a lot of weight and is still wearing his old, now baggy clothes (or if he’s gained a lot of weight and is hiding in too-big clothing), it’s OK to say, “Honey, let’s find you clothes that fit and show off your hot body.” If it’s a weight gain issue, a more sensitive approach may be necessary.
  • The bad personal style guy is probably the hardest to make over, because he actually has thoughts and ideas about his clothes, but those thoughts and ideas are BAD. With this guy, you need to insert yourself into his sartorial system. Buy him books about men’s dressing and get him a subscription to Esquire. When Esquire shows up every month, take your “YES” and “MAYBE” stickers from Lucky and tag all the things you wish he’d wear. When flipping through Vanity Fair, say things like, “Oh, Marc Jacobs wears Stan Smiths. We should go get you some this weekend.” And when you go shopping together, participate as he browses, go into the fitting room with him and have very firm opinions.
Regardless of which category your guy falls into, it’s always good to have some backup. Start reading Esquire and GQ magazine (bonus — profiles of hot actors!) and bone up on the rules of men’s fashion. Carson Kressley’s “Off the Cuff” is a great read, as is the What Not To Wear book, both of which are likely available at your local library. The What Not To Wear book is also useful if your man has some body issues or is a challenge to dress, which he probably is, if he isn’t 5’10” and 165 pounds. Plus, it has advice for ladies, too!
Have a sartorial issue you need solving? Let me know in the comments, or send me an email!
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