How to Bring This Up?

[Kerry]

guys can be kinda sensitive so I need to approach this very gently but am not quite sure how. my bf wears clothes that are way too big and don't really flatter him. I bought him jeans for Christmas that I think will be clearly too big on him (as my memory serves). I'd love to say to him when I see him that I want to take him out on a shopping spree so he can get what he wants and then I can make sure he's wearing the right sized clothes. I swear the jeans he had on when I saw him were 2 sizes too big. so how do I tell a grown man that his clothes don't fit him? help!!

[Alemap]

"Hey, do you know, you have such a great body. I think some better-tailored clothes would really flatter you. I'd love to take you shopping, to pick out some things together that are just your style and will showcase your [use specific examples of parts you find especially sexy, particularly ones you've mentioned before] more! Would you like to?"
If he says no to that, there's not much more you can do.

[kittyo9]

There really is nothing wrong with suggesting it! You can pose it as a curious question ("Sweetie, how come you like to wear your clothes so loose? Is it for comfort?") or an actual suggestion ("Hon, I would love to see you in some clothes that fit you better."). If he responds positively, you might then bring up the idea of taking him shopping. If not, you can bring it up again at a later time.

I tend to wear very plain clothes-- jeans and a T-shirt usually-- but my boyfriend often tells me he would like to see me wearing something more flattering. I don't like the way I look in general, so I don't put a lot of effort into my clothing selection. He wants to take me shopping, though, so he can show me things he thinks I would look nice in. All it took to suggest it was, "Hon, I would love to see you in some cute clothes. Maybe we can go shopping together."

[Darth_Taco]

"You're clothes don't flatter you. Here, lemme fix that." That's the nice way to say it :P. I tend to just make fun of him until he either throws things at me or gets a nice shirt (usually the first). Then again, I have the gay excuse :P. I so do not help the stereotype XP. Most guys aren't that sensitive over their sense of style unless they have masculinity issues. Hell, most guys seem to expect their girlfriends to fret over what they wear xD. Just don't go into mom mode and you should be good :P.

Oh, and quick thing. If he happens to sag his pants, pull them up until you hurt something @_@...

[Haley53]

I prefer the direct route, really. I tend to wear my hair pulled back into a bun or ponytail. I hate my hair. I get told it's the one thing I will learn (or should) to appreciate, but it is probably the biggest bodily inconvenience I have. :P However, my partner loves when I wear it loose/let down, despite the fact it can get frizzy, so he'll sometimes tell me "you should wear your hair down." "Why don't you wear your hair down more often? I like it when it's down; it's really pretty." Things like that are gentle hintings and they make me feel more confident. So I like Alemap's way. I'd be a little less verbose about it, personally, but saying something about really loving his body and thinking he'd look great in a more tight-fitting shirt might actually encourage him to want to try dressing in a more flattering way. I'd try and avoid using words/terms like "cuter" or "more flattering" simply because depending on his self-esteem, they could be taken the complete opposite way you mean them to be taken. :P

[Zapookie]

Yeah, just tell him that you like it when he wears so and so because it makes him look sexy or something along those lines. Soften the blow with a compliment, that usually works.

My SO wears baggy clothes too, but if that's what he wants to wear then I'm not going to stop him haha. When his pants sag at the back I pull them up for him and cop a feel of his butt hahaha.

[Rugger]

I didn't ask my partner. I told him for christmas that I'm buying him a new pair of jeans. His are full of holes.

You need to be direct with him, " Sweetie, Those jeans aren;t doing you justice. Let's go buy you a new pair. My treat"

[Alemap]

It may also help to inform him that butt-sagging jeans actually originated from prison-inmate code for indicating to other inmates that they were "easy", because wearing their pants like that allowed easier access.
Little-known, but true.

[CynicalQuixotic]

It may also help to inform him that butt-sagging jeans actually originated from prison-inmate code for indicating to other inmates that they were "easy", because wearing their pants like that allowed easier access.
Little-known, but true.

Urban legend. Snopes disproves it.

[Alemap]

Urban legend. Snopes disproves it.

I stand corrected!

[FadedSunrise]

LOL I totally still have this issue.

My SO has studied wushu most of his life, from the time when he was a little kid. Wushu training gear and uniforms are flowing and loose. He told me he got so used to wearing those items that it translated into buying other clothes. However, because he's been an athlete all his life, he has a very good looking body and its all being hidden behind baggy clothes, haha. I just try reminding him of what I think about it often, and he's gradually picked up on my hints, and bought better fitting stuff.

[Ianthe]

For the first year or so that my guy and I were together, I agonized over his clothing. He is just not the kind of guy that puts a lot of thought or effort into clothes, and struggles with finding clothes that fit. So when he wanted to go shopping for a jacket, I had him try on a few nicer tees just for kicks, and I made sure to gush over him when he came out of the dressing room, so he bought some of them. We ended up talking about his wardrobe a few months later, but I was very scared to do so because like you, I didn't want to hurt his feelings. It wasn't so at all! He is actually very thankful to have somebody willing to help him with his clothes.

Now, almost four years into the relationship? When I visit him, I go into his closet and start sorting into "keep" and "dear goodness NO" piles.

So, just be gently honest, and tell him what you'd like to see him in! He might be grateful for your input.