If you’re celebrating the day with your close friends, we recommend opting for comfort. You’ll probably eat way too much food and even indulge in the booze a bit. I once had a boss that told me he has a Friendsgiving where you’re only allowed to wear things with elastic waists, and I thought this was a genius idea! Go with a relaxed look (that can easily be worn throughout the holiday weekend) with a nice mule. This time of year, the food is stuffy, so you don’t have to be.
1) Beckett marled wool cardigan, $395 by Imogene + Willie
2) Bank cotton twill trousers, $150 by Adsum
3) Lightweight jersey t-shirt, $55 by Reigning Champ
4) Japanese slub crew socks, $28 by Rototo
5) Fort Worth mules, $170 by Sabah
6) Singular cuff, $155 by Miansai
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 business causal—so dark denim, clean oxford and a bit of a festive cardigan. Pair this fit with hiker boots just in case you need to jet before dessert.
1) Oxford stripe shirt, $195 by Gitman Vintage
2) Nordic cardigan, $195 by Adsum
3) Urban hiker, $225 by Solovair
4) Classic belt, $105 by Tanner Goods
5) Slim straight selvedge jeans, $188 by Levi’s Made & Crafted
Maybe they’re your in-laws. Maybe you’re meeting your significant other’s parents for the first time. First off, don’t load up on too much food—eat light and stay on a swivel for those hard to answer questions. Go for a smart and soft tailored look with an unstructured blazer. Yes, I have two options for shirts because you may get nervous, and both the sweater polo and denim shirt are fail-safe options, so just follow your sartorial instinct. Besides looking good, don’t forget to bring a bottle of wine—a thoughtful gift like this should win the parents over before you even step foot into their house.