Christmas Eve is a great time for comfort clothes – clothes that feel not only comfortable, but also unpretentious and familiar. For me, that means putting away some of the weirder leather jackets I’ve been wearing this year, and slipping back into a soft-shouldered tweed sport coat, button-down plaid shirt, and pair of tan, cavalry twill trousers. Casual enough for lounging after a big meal; presentable enough to see grandma.
If you wear such a combination today, pair these things with some dark brown, pebble grained boots or shell cordovan derbys. You can also go for an all-American look by wearing a pair of penny loafers (if the weather is warm enough) and swapping out the cavalry twills for some khaki chinos. If your shirt is light colored, you can wear a tie (something on the casual side, such as wool, ancient madder, or knitted silk). If it’s dark, like Woody Allen’s above, I recommend going tieless and unbuttoning the first two buttons. This will not only give you a better neckline, but it’ll also make you seem a little more relaxed. You know, like you’re in comfort clothes.