Join Date: Jun 2008
I've got a nice grey wool sport coat by a company called Matinique, and I wear it all the time. Personally I never wear it without a collared shirt, but that's because I'd feel like a d-bag- if you can do the whole "indie rock sport coat and graphic tee" thing, more power to ya. For pants, anything presentable, really- no ragged faded denim, but I wear mine with dark jeans all the time. Sneakers are fine too if they're not too loud- Chucks or Eras or Sambas are what you want to be thinking here.
Really, the beauty of a sport coat/blazer/whatever is that it straddles the line between casual and formal. Wear it with a tee, jeans, and sneakers and go to a concert, or throw on a collared shirt some cords and laceups and head to the yacht club. For the versatility alone I'd reccomend adding one to your wardrobe.
Out of curiosity, how old are you? If you're too young that might be why it doesn't feel quite right. I'm 21 and only recently did I feel like I had the gravitas to pull it off well. If you're still in high school it can go two ways- either you'll be the weiner with the ill-fitting jacket who's trying too hard, or if you've got the right amount of attitude, you'll be the fucking flyest looking kid in detention.
Just something to think about. Good luck with the purchase, or non-purchase, whatever.