Having dinner with your family is the best but oftentimes can be intrusive with questions from relatives that you only see sparingly. Dress semi-formal to let everyone know at the dinner table that this isn't your first rodeo, and you can banter with the best. Go for a smart casual look—hardy herringbone pants, an oxford button-down that allows you to roll up your sleeves to help clean dishes and a cardigan that's heavy enough to wear outside but comfy enough to wear while napping on the couch after the tryptophan kicks in.

First off, don't load up on too much food when meeting the future LP's (life partner) parents. You want to look good, so eat light and stay on a swivel for those hard-to-answer questions. Go for an elevated yet soft tailored look. Start with an unstructured wool blazer and tuck a bandana into your chest pocket like a pocket square—you'll be meeting new people, so you need something to wipe the sweat away to hide that nervousness. Layer an understated crewneck sweater over an oxford button-down. Classic and comfortable enough to throw the football with your future brother-in-law or help bring in firewood.

After Thanksgiving you're probably gearing up to reheat leftovers for lunch, maybe play some touch football with friends or brave the shopping scene. Which means you need an outfit that is comfortable enough to sit at home on the couch but versatile enough to walk in the cold or wait in line for deals. A thick-down jacket has a utilitarian sensibility to it and keeps you warm. Pair it with a thermal, a crewneck for extra insulation and a pair of relaxed wool pants—the elastic waistband is a sartorial cheat code for the holidays.