Though you're all grown up, the word "sportcoat" still dredges up memories of communion/bar mitzvah/visiting the Home to lie to your grandmother about going through with communion/bar mitzvah. Well, sportcoat this: Elmer Ave.
Started by a NoHo quartet of skateboarders/rock-guys, Elmer infuses sportcoats with attitude, a task even more impressive than infusing tofu with flavor, with an even more meat-like result. Each piece starts with a slim-cut jacket base of silk, wool, and/or high-grade polyester, then gets details like custom-made, gold-plated buttons before receiving the ballsiest treatment: hand silkscreening/spraypainting (usually the work of vandals, now the work of dudes who heart the Vandals). Designs range from "The Duke" (a smoking-jacketish affair w/ oversized 4-sided crest on the back), to the latticed and guitar'd "King", to "Bullitt": whose cross-stripes subtly conjure up Steve McQueen's 2nd greatest role (right behind the role of posthumously representing all things badass).
EA also makes custom jackets from a broad range of refurbished vintage gear -- they're pricier, but you've still got a little left in your "bar mitzvah fund".