Picture this: you fall for a girl on a trip, sweep her off her feet, propose in a matter of a days and now you have to plan a wedding in a faraway location with a family that's not your own and your boys back home too broke to fly out. If life were a quirky date comedy, you might be introduced to a new family and a bunch of groomsmen you've just met. And among the many other things on your mind, you might be worried about what to get them as groomsmen gifts.
Real life can be much more mundane than that, though - whether it's that you're getting married far away and your best boys can't make it, or just that your fianc has a distant cousin she adores that she wants in the wedding party as your groomsman, you just might end up with a groomsman you don't know very well. If they get groomsmen status on basis of geography (i.e. they're local and available), you're probably already working on getting to know them. Boys nights out and the activity of their choice could give you a great handle on what to get them as groomsmen gifts.
Keep in mind that you don't need to go all out on research, though - even if they're strangers to you, your bride-to-be probably knows a little bit more about them. This is not the time for subtle recon, so ask her straight out for tips on what to get them as groomsmen gifts. Point out that you want to get to know them better, too, especially if they're relatives of hers. You'll win points for displaying interest, and get in good with your groomsmen when you give them gifts they actually want.
If you want to know what they like, though, the best option is always to ask. Sports are an easy bet, so find out what games they watch or play, and get them something related to their game of choice. Keep an eye on their vices - liquor or cigars, perhaps - and choose groomsmen gifts accordingly. Executives are relatively easy as well. Leather portfolios and fine ink pens stand up to the test of time, and they're classy, too.
Tried your best and still got nothing? Something personalized is always a good option. If you don't know them well enough to give them something they'll like, it's a good bet you at least know their names. Make it easy on yourself by giving them monogrammed groomsmen gifts. You can get a great deal of things personalized, from beer steins to flasks to cigar humidors or baseball bats. If you can't give them something that shows you listened when they talked about their hobbies, at least give something that shows you listened when they told you their names.