An olive plaid wool blazer and grey wool dress pants are absolute wardrobe heroes if you're figuring out a stylish wardrobe that holds to the highest men's style standards. For something more on the casually cool end to finish off this ensemble, introduce a pair of brown suede desert boots to your outfit. When spring is in full effect, you'll love this getup as your uniform for transitional weather. So if you need outfit inspiration for dressing in your fifties, this getup is ideal.