I prefer to buy my artwork directly from the artists. This often means meeting them at an art fair or at the merch booth of a concert. Lately, as I've been meeting more young artists who are early in their careers, I've been commissioning new pieces that fill a need in my life. I consider this money well spent, as I'm supporting an artist and also getting something pretty to show off.
I would love to see what you've gotten. I'm a pretty regular concert goer and always make sure to hit the opening acts. Best place in St. Louis for me right now is The Ready Room. Love it. Tiny, small-medium acts, intimate. Meeting the acts is some of the best parts of the show. Last show I saw there was G Love and Special Sauce, and the band that opened for them was Ripe. Both very very good live. Bought Ripe's CDs that they had, but like the 22-20s, the CD just doesn't capture the live energy. It's a matter of production I guess, but it's always disappointing. Before that I saw the Dead Deads which holy fucking shit are no joke amazing. Their drummer is so exciting to listen to and even better to see live. Can't wait til they come back through St. Louis. And that show was to see (hed) p.e. which is a guilty pleasure band of mine. Then, and this is a tip for kids of all ages, if you want to look suave as fuck, you should take your date to a gallery opening. There is usually free drinks, and you can do your homework on the artists there before you go in order to better help the conversation along. I just did this with the current girlfriend, and we met Daniel Burnett who is doing some neat things with bringing graffiti indoors. If I had the money, maybe I'd do my best to help him out, but his things are pricey! Also, post pics of some stuff you've bought. let's see your taste in art.