Alan Flusser and Off the Cuff have put together a great little iPhone application called BeSpeak, which helps in picking out colors and patterns to wear with your complexion and body type.

bespeak
Hit the refresh button on the bottom to auto-generate new combos, or customize and save existing ones. I’ve seen a couple of bugs so far (it recommended a solid white tie on one of it’s auto-matches?) but overall it’s a decent tool.

For more matching ideas, here are some older scans from Men’s Ex that I posted last year: Combining Patterns