This one is a bit of a loaded question for me, but I'll list them all out and explain why, because I can. (note that this isn't in any particular order)
Couple's Mask: I simply adore this mask for the quest you go through to get it, as well as it's meaning. Anju + Kafei are best couple <3
Captain's Hat: I've had a strange fondness for the Stal species in the Zelda series. From the goofy Stalchildren, my sparring buddy Stalfos, to the awesome Stallord of Twilight Princess. But, its clear I've always had a fondness for skeletal imagery in general. And seeing it's a skull-like mask, of course it's going to tickle my brain lol
Garo Mask: The way you get this mask is the least interesting, aside from asking the question as to where the Gorman Brother managed to get them. But, the Garo themselves are more interesting. I could talk about how neat they are, but this post would be a lot longer than it already is if I did.
Honestly the more I write this, I could talk about all 24 of them. All of the masks have their own merit to them. Even though some you'd only use once in the game, they hold a special place. And just saying that alone is what makes Majora special to me, and enforces what the Happy Mask Salesman says at the end. Happiness, in some form, is filled within these masks.