This combo of a black leather jacket and grey vertical striped wool dress pants is a must-try casually classy ensemble for any modern guy. Introduce a pair of white sneakers to the mix to make a standard getup feel suddenly fun and fresh. So if it's a roasting hot warm weather day and you want to look dapper without exerting much effort, this look will do the job in seconds time. Wondering how you should dress as you pass the big 3-0? This outfit is a good illustration.