You know how guys are — unwilling to ditch their favorite baseball cap/backpack/sneakers that have seen better days until they find a replacement they can love equally. It may take some convincing, but in time they all learn that they can have their creature comforts and be stylish too, and there’s no time like the holidays to prove that point (’cause every great gift proves a point, right?) Scroll down for our roundup of the best picks for your boo that are both functional for him, and nice to look at for you. We promise, six months from now he’ll be wondering how he ever lived without his UGG house slippers.

featured image by Kristen Kilpatrick