For an effortlessly sleek ensemble, reach for a navy plaid blazer and blue jeans — these pieces play brilliantly together. If you want to easily up the ante of your look with one single item, why not complete this outfit with a pair of black leather chelsea boots? So if you're scouting for an outfit that's sharp but also feels totally season-appropriate, this one is great. A look like this can make any gent in his 50s look better than everyone else in the room.