There comes a time in every guy’s life when it’s time to swap those beloved sneakers for something a bit more stylized. Fret not. These desert boots and chukkas are just as comfortable as your dependable kicks yet they give the jeans and T-shirt formula a much-needed injection of sophistication. Pair any of these styles with cuffed chinos and a button-down for a foolproof look this spring and summer. The details: Brands include Sebago, JD Fisk and Ben Sherman.