A red party dress is such a classic, festive symbol of holiday season. In a flattering fit-and-flare shape with pleated chiffon, this version reminds me of something Betty Draper would wear. The ’50s-inspired silhouette remains timeless today, but especially works when paired with modern details like messy, undone waves, a matte red lip, and a sleek, single-sole heel. I love that the pleated chiffon offers movement too, so the shape isn’t structured or stiff. The overall effect is playful (twirling being pretty much mandatory in this), and still chic enough for a formal affair.