Good question, and I’m happy to share.
For spirits, I almost always use one of three glasses: The Glencairn Scotch Whisky Glass, the Riedel Sommeliers Series Single Malt Whisky Glass (pictured), or Bulleit Bourbon’s oblong tumblers. Most brown spirits go in one of the former glasses. White spirits often in the latter. No real reason for the separation, just habit really.
Of the two whisky glasses, I prefer the Riedel. The Glencairn is more popular in the industry and at events, but I find it concentrates the alcohol vapors too strongly, trapping them in the glass — and making it hard to smell anything but harsh alcohol when you take a sniff. The tulip mouth of the Riedel lets some of the alcohol escape, and while it also lets some of the nose of the actual spirit out, I find this is a small price to pay for the advantage of aerating the spirit, and ultimately it results in a clearer impression of what’s being tasted.
For wine, I try to use the traditionally appropriate glass (I have a wide selection of Riedel stemware from a variety of its product lines, quite a hodgepodge now), in as large a bowl as possible. For inexpensive wines (like boxed wines) I may use a standard, off-the-rack smaller wine glass or stemless wine glass for the sake of simplicity, but for more serious wines I try to go with the big stuff. Most of my glasses are from Riedel’s Vinum or Vitis series.
It’s true that glassware does impact your experience, so it’s not foolish to be thoughtful about what you pour your $300 whiskey into. Hope that helps. Happy tasting, and remember: Glassware makes for a great Christmas gift — and you can carry it on an airplane, unlike a bottle of wine or whiskey.