Changing a Guy's Wardrobe: Easy ... or Impossible?

Just the other day, we talked about clothes and whether they work for Christmas gifts. Well, that got me thinking about a female friend of mine who has always contended that the easiest thing to change about a man is his wardrobe.

I've found that's somewhat true — and that, in fact, plenty of men are really appreciative of any fashion advice they get from their girlfriends. But there are a few caveats:

1. He can't be too invested in a personal style or manner of dress before you meet him. If he's a hipster who wears nothing but skinny jeans, pointy half-boots, and button-downs that are too tight — and you're hoping to make him into more of a Banana Republic poster-child (or vice-versa), you'll have a tough time. And perhaps rightfully so. Personal style — and even lack thereof — is, to some extent, a reflection of personality. If he's trying to say I'm a wacky, unconventional guy! with his outfits, and that's a message that makes you uncomfortable, you might be better off with someone who's happy in business casual — or a simple pair of 501s. While it's possible to make suggestions about sneakers that might be just as comfortable as his New Balances but slightly more stylish — or about how nice a merino wool sweater might look on him (while also keeping him warm) — there's a difference between helping him look his best (or at least better) and trying to transform him completely.

2. Don't do it right away. Wait until you've been dating him a few months, and you have a nice rapport.

3. Do it gently and kindly. Make your sartorial suggestions in a supportive manner, in an effort to make a person you care about a little cuter (or possibly a little more professional-looking, particularly if he feels like he's not being taken seriously at work). Don't say, "Do you realize how horrible those old pants are?" Say, "I have no interest in helping other girls clue in to how hot you are, but I think these jeans could be really great on you."

4. Take it slowly. One step at a time. If you demand too much all at once, you could come off as too bossy. (And new clothes are expensive!)

But, I think my friend is right. If you meet a guy you like who doesn't pay too much attention to his clothes, it's no reason to write him off ... because that is something you can work on with him. Eventually.