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.
Alright a leather jacket is a must for this style. The jacket takes you to the next level quite easily. Most jackets will be good, just do not throw on a black leather jacket and a white T-shirt expecting no one to call you a greaser.