1. Christmas in Connecticut (1945)--This is a major moment, because until two days ago, I had never even seen this movie. In fact, after seeing it I had planned to rank it third on this list, but after a bit of soul-searching, I had to bump it up to the top slot. Barbara Stanwyck is witty and gorgeous. Dennis Morgan is fine. The plot is the perfect mixture of hilarious mixups and romance. The house is fantastic. And, it's got S.Z. Sakall, who is without a doubt one of the most adorable character actors in the history of Hollywood. (The man's nickname is Cuddles, for Pete's sake. It does not get cuter than that.) And, you know, the clothes, like the GIANT SPARKLY MONOGRAM:
2. White Christmas (1954)--Seriously, it's got Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen, which are four excellent reasons to indulge in some cinnamon cocoa and couch cuddling on a snowy winter night. Plus, the title song is one of the most iconic Christmas songs, and it's guaranteed to make almost everyone feel warm and fuzzy. And, you know, the clothes:
3. Holiday (1938)--Not really a Christmas movie in the traditional sense, but it does take place during the holiday season (with a climactic New Year's Eve engagement party). Cary Grant. Katharine Hepburn. Already, it's a winner. Add to that a wonderful "money can't buy happiness" plot, plus some great witty (and acrobatic!) moments and between two of the greatest actors of all time, and you've got a fabulous movie. Plus, the clothes:
4. Holiday Inn (1942)--It covers all of the major holidays, but it's really a Christmas movie. Bing Crosby wins again, and he's accompanied by Fred Astaire (so you know there's some great dancing!). And, clothes:
5. Meet Me in St. Louis (1944)--Judy Garland makes Christmas. Enough said. And, that dress:
I will give an honorable mention to It Happened on Fifth Avenue, which I need to see again because it's been a while. Who knows? It may even displace one of the movies in the top five. I just don't remember enough about it. But I do remember the coat and hat (priorities!):