Picking out the perfect outfit for your holiday shindig can be stressful. Whether you're celebrating with a family dinner or a big party, there are so many factors to keep in mind when choosing Christmas Day outfits, Hanukkah ensembles, and all manner of party attire. You want to be festive but not kitschy, and cool but still family-time appropriate. To help you find an outfit you won't end up regretting, we've rounded up some easy ways to take potentially problematic outfits and make sure they're perfect for your festivities. We have some tips on how to style a cheery sweater, a sparkly dress, festive colors, and more. Scroll down to see the fail-proof ways to wear classic holiday outfits you won't regret.