I guess it depends where you live. I'd go for sneakers like these
http://www.freshnessmag.com/2008/09/10/ ... ker-boots/ for day look and some boots for night look, maybe something like this
http://dsouthsider.blogspot.com/2010/10 ... boots.html . Don't forget the accessories! Get some of those black leather wrist skins and some cool male bracelets. Don't forget something for around the neck, I'd wear two pieces around the neck, make sure they compliment each other, for example this
http://lastheplace.com/2008/02/05/rock- ... with-ms-2/ with a black piece that hangs lower then the first necklace, something like this
http://www.stylesalt.com/product/409267 ... ace--black
And of course, the belt! Nice prominent buckle on a black leather belt looks awesome for the night look.
For the day look, tone down the accessories, use less of everything.
If I may suggest one more thing, which may seem a little gay to you, but looks really really good. For the night look, you could use a little black eyeliner on your eyes. Make sure it doesn't have any shiny elements. Make sure it's sharp enough not to make the line too thick. Apply it to the edge of your eyelashes on the upper and the lower side and gently smear it. Google how to apply it properly. There is also a clear mascara you can use. It will enhance your eyelashes without making you look gay. I know most guys are not into make-up, but it makes a huge difference. Imagine how much more intensity there will be in your eyes and it really goes well with this look you like.
I hope this helped, tell me what you think.