Thanksgiving is a couple of weeks away and it can be a tough time for a lot of guys to know what to wear. I remember hating it as a kid because my cousins could wear T-shirts and jeans while my mom made us put on button-up shirts and sweaters. It’s funny to think about how things have changed.

Thanksgiving has become the perfect High/Low holiday. Some of you will spend it eating pizza and wings while watching a football game and others will be gathered around a table with the formal china and silverware polished and ready to go. Regardless, you want to be able to look sharp and still be comfortable for the turkey-induced coma you’ll experience a couple of hours after eating.

Here’s a good baseline of what to wear.

 

Clarks Originals Desert Boot: These are the original chukka and there’s a reason they’re still around today. Comfortable but durable – they’ll look good dressed up or down and will keep you dry on the trek from the car to the house during that winter storm. $120

Dockers ‘Alpha Khaki’ Chinos: These are not Best-Buy-employee khakis. In fact, they’re endorsed by overall manly man Bear Grills. The construction, cut, and material are all going to be durable like a pair of jeans, but they’re still khakis so the overall appearance is more dressed up. They have a good taper down the legs so they’ll be slim without making you look like you stole your sister’s pants. $60

Gap Waffle Henley: Choose a warm color like this olive-green to be appropriate with the season and also to contrast off the grey of the khakis. This is going to provide the low in your High/Low so you don’t end up sticking out like a sore thumb. $30

Gap Herringbone Blazer: Herringbone is definitely a winter pattern and the new navy offering from Gap looks to be pretty promising. It’s cut a bit short so it will look casual as a jacket, however it’s still going to be your High because it’s a blazer. $98

Bill Adler Nubuck Leather Belt: Nubuck has a much softer feel and look than traditional leather. The brown of this will complement the sandy color of the desert boots without matching it directly and the texture is going to imply comfort without sacrificing formality. $28

PS. Did you know I do private style consultations? I can help you dress better according to your budget and your needs.