I love everything about my boyfriend, except the fact that he dresses very ugly. I work/hang with people in fashion and cosmetics and I feel it becomes an issue when we are out around those types of friends/people. I'm not asking for much, I am just sick of seeing stupid graphic tshirts and pants. I feel embarrassed when I'm dressed really nice at a party, and so is everyone else, except my boyfriend. I need to know what's acceptable to either tell him straight forwardly, or give hints? I don't want to hurt his feelings or offend him ... but it is an issue with me that I feel will be a constant problem since its directly related to my career/social life too.
Some people are naturally good with fashion, others are not. It's just the way we are born and how we see colors and designs.
I too am a poor dresser. I used to wear tattered t-shirts, and tucked them into my track pants. Yeah...you heard me right.
You might try suggesting (or just ordering him) a subscription to a magazine like GQ, or start buying him nicer clothes. He will not have the eye to be able to select nicer clothing so this will probably require some push or initiative by you. Skip the suit and tie and go for collared shirts and sweaters that fit nicely and comfortably.
He basically needs to be tutored on what looks nice and what types of colors/patterns make a man look good. He's spent his whole life paying no attention to fashion or style. There is little to no capacity for him to learn it on his own now. I would avoid blaming him about this problem. He cannot help it. It's like telling a person who's bad at math to suddenly be awesome at complex calculus and derivatives. It just doesn't happen without a lot of tutoring.
I suspect your boyfriend has a very laid back job (i.e. mechanic, tradesperson, IT), and not a business-type job. If he is not expected to dress well at work, he pretty much has zero reason to dress nicely...period.
Don't DARE broach this subject yourself. Fix Boyfriend up with a fashionable guy "Dude" that USED to dress like Boyfriend and now speaks volumes on how Dude's life has changed for the better. This guy Dude will have to genuinely LIKE the Boyfriend in order for the sale pitch to be solicited. Best if Boyfriend asks his new buddy HOW come Dude gets ... whatever the Boyfriend covets of Dude's.
"Oh hey this would look really good on you" shoving him a few outfits here and there while out shopping with him. Explain that he needs to dress up a bit on nights out with other professionals and that he needs to make an effort.
Or just tell him how you feel saying you feel embarrassed with him as he's not dressing up to the occasion and would prefer if he sorts his wardrobe out for those nights. Tell him how good it would make you feel if he did that for you.
Yeah I hear you. When I'm with my boyfriend and I see some nice article of clothing on a guy or anywhere I just say, "Omg I love that style of shirts on guys" I would hope guys pay attention to that stuff. Then maybe propose going shopping together and you can "guide" him ;) in the right stores lol