Watching movies is probably one of the best ways to find a style you like. Actual fashion shows and magazines tend to present conceptual or high fashion, which, to be honest, is pretty fucking pretentious. Movies are great, though, because there are literally teams of people whose sole job is to fully understand the actor and the character that the actor is playing, and then build a wardrobe around him. If you think about it, all you have to do is find the movie character you admire most or are similar to and then blatantly steal his concepts.
The Rebel: Tyler Durden (Brad Pitt) – “Fight Club”
Tyler Durden’s style is basically Jimmy Buffett meets punk rock: crazy patterns, leather jackets, yellow sunglasses. Somehow, when it’s all thrown together, it appears as if he’s not trying. That’s the hard part about going for “out there” looks–if you try too hard, it’s painfully obvious. Maybe don’t wear a red leather jacket with a Hawaiian shirt, but get some color in your life.
The Modern Cowboy: Raylan Givens (Timothy Olyphant) – “Justified”
Yeah, yeah, “Justified” isn’t a movie. I don’t care, because I don’t think anyone has managed to pull off the Canadian tuxedo as well as Olyphant has in the last six years of “Justified.” Please note that I am NOT advocating you go buy the Stetson he rarely takes off his head. You can’t pull it off, I’m sorry. Take some notes from the way he can seamlessly go from worn jeans and a loose button up to dark jeans, a tie, and a blazer and still look equally suave and threatening.
The Preppy Bachelor: Tripp (Matthew McConaughey) – “Failure to Launch”
Say what you will about how good of a movie “Failure to Launch” is, but it’s certainly fun. McConaughey absolutely kills the lazy prep look, too. Most people associate the casual prep look with loose button ups, short shorts, Sperrys, and wayfarers. This is sort of true, but it’s annoyingly cookie cutter and it reeks of a sophomoric, try-hard frat guy. Here’s my biggest complaint about most guys going for Friday night prep: most of your shirts don’t fucking fit. You can wear a loose Oxford comfortably without it swallowing your torso. Just watch the damn movie. Also, note the thin strap holding his sunglasses. Thick croakies are out, boys.
The Lovable Schlub: Dewey Finn (Jack Black) – “School of Rock”
It’s funny, because the clothes that good ol’ Dewey wears for much of the film are his attempt to look “lame.” Except, as he realizes about everything else, doing what he does is actually kind of cool. Yeah, patterns, bowties, and sweaters might be a bit much altogether, but just because you share Jack Black’s body type, it doesn’t mean you have to dress like his character in “Orange County.”
The Suave Operator: Thomas Crown (Steve McQueen/Pierce Brosnan) – “The Thomas Crown Affair”
Whether you prefer the 1968 or 1999 version, Thomas Crown is an enduring icon in how to dress if you’re a billionaire. Are you a billionaire? If not, that doesn’t necessarily mean you can’t emulate his style–just take it easy on the power suit if you’re still a desk jockey. You should dress like Thomas Crown if you want to look refined but not ostentatious. The truly rich don’t need fat knots and heavy shoulders to portray their wealth, and you don’t need them either if you’re just looking to wear the fuck out of a suit.