Is my Man - A BOY?

QUESTION: I've been going out with my boyfriend for almost a year. We met in the gym near my house and got along real well from the start. My only problem with him is that he dresses like a teenager. He's always wearing big jerseys, baggy pants, doo-rags, and sneakers. I don't think he owns a tie or a dress shirt or a pair of casual pants. I don't need a man to always wear a suit and tie for me, but I'm 38 and he's 36 and I'm starting to get a little embarrassed when we go out to dinner or whatever and he looks like an 18 year old thug. I've asked him to try a few new changes in his wardrobe but he won't. He says he's "Keeping it real." He's a nice guy, but I'm getting tired of this. What is he thinking? What should I do?

Chuck: Let's try looking at things from your boyfriend's perspective for a minute. You didn't say what he does for a living, but if his job does not require him to dress up, he may not have a lot of experience with it, and therefore have little appreciation for how he could look. How and where he was brought up could have played a part in this.

That said, you should also define how embarrassing his outfits are. I don't have a problem with t-shirts and jeans (even loose ones), but if he's a grown-ass, 30-plus man walking around in, say, Makaveli Branded jeans (they have 2Pac's face embroidered on them, for God's sake) and "Stop Snitchin'" t-shirts, well, what's really going on? He may be trying to hold onto his youth this way. And to be 36 and doing that is NOT keepin' it real.

My solution? Take your man shopping. Find a nice men's store that carries a decent variety of clothes and get him to try on some different stuff. Make it fun. Flatter him. And you might find that he's ready to move to the adult table, after all.

GARLAND: Sounds to me like he's "keepin' it real"... REAL juvenile!

Unlike my man Chuck - I'm a little less forgiving with a 36 year old man that won't put on a button up shirt even once in a while. Granted, he might have a job that requires jeans and doesn't have a certain dress code, but he's not a teenager and every so often he's got to try to dress a little more mature.

Jerseys and baggy jeans are cool if Big Macs are always on the menu and you spend all your Friday nights at the video arcade. But you can't go into nicer restaurants, or certain clubs, or other places wearing Timbs and T-shirts that read, "If you see the cops - Warn-a-Brother."

Some guys unfortunately have poor fashion role models. Maybe their dad or their big brother or their boyz never dressed outside of jeans and pull over shirts. I think a lot of guys are kinda' intimidated with matching shirts and ties, and matching belts with shoes, and has anyone ever really looked at cuff links - come on!!!

I think you need to take him to a nice store with the kinds of clothes that you want to see him in. Encourage him to try on some outfits, make him comfortable in linen shirts, put some nice ties across his chest. Try to urge him to pick up an outfit or two. The first step might be a small one. But whatever you do, don't try to make him into someone he's not. Maybe he'll mix in the two different dress styles for you, but he's still going to want his casual gear around too. That's fine. However, if none of this works, and he still refuses to consider even a slight change, then sit back and assess what it is you want and expect from this relationship. You may just have to accept it, or you may have to be willing to leave him and move on.