It’s been said that dressing well means dressing for the occasion, which means dressing for the holidays depends on what you plan to do to celebrate.
I usually spend Christmas at home with the family, but on some years, we go out to a Chinese restaurant, where we celebrate the birth of Christ by eating chicken feet. Both are extremely casual gatherings (it’s hard to be formal with a chicken’s foot in your mouth), so I dress accordingly. Wool trousers get swapped for chinos or corduroys; spread collar dress shirts get traded for white oxford cloth button downs; ties are left behind for shetland or Fair Isle sweaters; and if I can work it in, I’ll wear dark green socks because they make me happy. I find the ensemble to be much more in tune with the day’s mood.
For New Year’s Eve, however, I encourage you to dress it up. If you can take your partner to a formal New Year’s Eve party or symphony, wear a dinner suit, black bow tie, and evening shoes. A Suitable Wardrobe has a pair of black velvet slippers and patent leather formal pumps that would be good for such occasions. If you’re going to something less formal, say a nice restaurant or bar, wear a navy suit, white dress shirt, and a pair of well-polished, black oxfords. You can accent your ensemble with a white pocket square and necktie in either black or silver.
New Year’s Eve is perhaps one of the most festive occasions of the year. Use it as an excuse to wear your best clothes, and your best clothes as an excuse to do something fun.