Male Fashion Movies

Yes, The Boardwalk Empire and Madmen are my favourite series in terms of outfit selection.

the devil wears prada- its a good movie and they talk about good designers.

James Bond flicks, Fight Club at the beginning, and WallStreet

Equilibrium (with Christian Bale), and about designers (Yohji Yamamoto) "Notebook on cities and clothes".

I too am looking for more movies where there's an emphasis on men's fashion, but there are a few that i can easily think of:
1.) Alfie (1966/2004) Both the michael caine original and the jude law remake have fantastic (and i mean FANTASTIC) men's style. I just want to be them everytime i see that movie. A perfect hollywood visual style in the remake (with heavy 60s influence), while the original is very 60s, and of its time.
2.) Lucky Number Slevin (2006) Josh Hartnet looks fantastic in this picture, seriously. From argyle sweater vests to big 3/4-length P-coats. Brilliant.
3.) Wicker Park (2004) On the subject of Josh Hartnet, this one is also great, a bit more reserved than the above, but still some great winter (Chicago) fashion through-out
4.) The Adjustment Bureau (2011) Matt Damon plays a presidential candidate so obviously he's in suits for most of the movie. Unlike the younger, hipper look of Josh Hartnet in Lucky Number Slevin, Damon plays off a much more professional businessman-like quality with very reserved suits. Mostly blue in theme.
5.) Gangster no. 1 (2000) British Gangster/crime film set in the 60s, so it has brilliant 60s men's fashion with tailored skinny suits for days! Paul Bettany looks killer, literally!
6.) Inception (2010) This one i think most people recognize as a very stylish film, both in effects and in wardrobe. Especially Joseph Gordon Levitt, who looks brilliant in a 3-piece suit.

on top of that i'd recommend these all as movies, themselves. They all rank among my favourites. So, it's worth watching them all, especially for all the brilliant dapper men's fashion