Forget summer celebrations or vacation packing — when the holidays roll around, styling requires more consideration than any other time of year. We're talking back-to-back events (your work party, their work party, or that random potluck you forgot about), and then, of course, the more momentous holiday occasions: Christmas dinner, community gatherings, and New Year’s Eve itself.

The holidays amplify everything — and your outfit becomes part of the season’s storytelling. There are also multiple...