Try teaming a blue bomber jacket with dress pants if you're aiming for a neat, stylish ensemble. If you wish to easily tone down this look with a pair of shoes, why not complement your outfit with black leather low top sneakers? When you're having one of those dreary fall days, sometimes only a kick-ass look like this one can brighten things up. This ensemble proves that figuring out fashion as an over-50 gent is quite manageable.