Sensible optionRiver Island, $37 
Splurge option
Our Legacy, $245 
Why dad needs it: Back in his day, your dad didn't need online stores with hundreds of brands, gigantic sneaker collections, and never lined up for a brand to drop at a store. All he needed to look fresh was his trusty denim jacket. He probably wore it to death or lost it during a wild night of his youth, so pay homage to where you inherited your style be re-upping his denim jacket game.