Yes and no.
In high school, I used to listen to a lot of street punk and Oi, and that really affected they way I dressed. As I got into college, I 180'd to a more relaxed stoner bro-look as I listened to more reggae and Sublime style punk/reggae. I think this was my rock bottom, style and style wise. Luckily I started listening to more hardcore and punk. This also came with a renewed interest in style. Now I listen to hardcore, old pop-punk, and a good variety of all kinds of other music. When I'm at home and on the weekends, I wear slim or straight-leg denim, chucks or vans, a plain t-shirt or a plaid shirt. This probably reflects the music I listen to pretty accurately. However, when I'm at work, the OCBD and chinos doesn't necessarily mesh when I'm listening to Down to Nothing on my iPod.