Our pick: Valentino Crystal Tan-Go Stilettos ($1,395)
Why it's a holiday staple: You can never go wrong with a great party-ready heel. If you're feeling extra festive, opt for a louder metallic finish or a standout jewel embellishment. But for a subtle play on detailing, we're loving this all-over crystallized finish. It's sparkly, fun, and fancier than your average black ankle-strap pump, but it doesn't take away from the fact that you can virtually wear this shoe with everything, from a pencil skirt to a lacy cocktail dress to a shorts-and-tights combo.