Say the word "whimsy" and you've got my attention -- I love anything fun and slightly wacky, but not necessarily ridiculously over the top. These Wobble Cognac Glasses are great, I think, because they look interesting without sacrificing any class. They were designed with bouquet, temperature, and volume in mind, and the delicate shape is said to enhance the pleasure, deep color, and movement of the drink (and also the glass to some extent, obviously). Made of hand-blown glass and available in sets of two for $50.
Via Book of Joe