Prada 'Levitate' Wingtip - This shoe encapsulates the versatility of the classic brogue. With a trainer-like sole it's the best crossover shoe I've seen. Kudos to Prada for this. Now to try hunt down a pair.
If you're not going to run, don't wear running shoes. 16 Ways To Dress Like A Grown Man Invest in quality. Every man should own a black lace-up shoe (they match everything) and a few slim, pointed ones.