Try different designs: Earhook or earbud? It's hard to know what will feel comfortable until you try both types. If you wear glasses, remember that using an earhook or stereo headphones can be a real pain--your glasses and headset/headphones compete for space in the same spot! Ask friends and colleagues if you can try wearing the models they own. (For hygienic reasons, and as a courtesy, you should use new ear covers, so that your friends won't be offended when you wedge their headsets into your ear canal with reckless abandon.)

Determine your usage habits: If you're the type of person who will pop a headset on and off a bazillion times a day, consider a hookless headset that goes straight into your ear--no over-the-ear jockeying or two hands required. On the flip side, if you plan to leave a headset in your ear for extended periods of time, think about whether an earhook headset would be more your style. The design might make the fit more secure.

Figure out your style and preferences: A shiny silver Bluetooth headset may look appealing in its fancy packaging on the store shelf, but how will you feel when you wear it? Visualize the contraption on your ear. Remember that whatever headset you choose, it's visible, and like eyeglasses, it will be part of your face. If you're considering going the stereo-headphone route, keep in mind that these products are not usually discreet.

Ask around for feedback: While you're taking your friends' headsets out for a spin, ask them how happy they are with the performance. How good is the call quality? Can you depend on it for business calls? How frequently do people on the other end complain about voice distortion or annoying background noise? Do the advertised talk and standby times live up to the maker's claims? After a day in the office with the headset stuck to your ear, do you feel any soreness? If you are an audiophile, the stereo experience may not be up to your standards. Ask like-minded music fiends for their recommendations (and glean what you can from user reviews).

Confirm compatibility: Make sure that the headset you plan to buy will support the cell phone you own; some Bluetooth headsets do not support all Bluetooth phones. Many headset manufacturers provide a compatibility list on their Web sites, where you can search for your phone's make and model.