Will it look as good on your head as it does on the rack?

Two generations ago, leaving the house without a hat was akin to walking down the street without shoes—and the style of a man's hat told you a lot about the man who wore it. Well, times have changed, and aside from donning the occasional ball cap to shade the eyes, few men would even consider crowning their domes with a fashionable hat of any kind. Yet men's hats are beginning to make a comeback in certain "hip" circles, and hat-wearing trendsetters are again being spotted on our nation's streets. So how, in this day and age, does a man go about choosing and wearing a hat?

Bill Prince is deputy editor of GQ magazine, the nation's foremost guide to men's fashion. Here he offers a primer for those thinking about dipping their toes, and heads, into the brave new world of men's hats.

• A style statement. In the old days, hats were practical: they kept the cold out and helped hide dirty hair. But in these days of efficient heating and daily showers, the only reason to wear a hat—outside of protective helmets—is to say something about yourself. So if you think you want to wear a hat, you have to be the kind of man who's comfortable with the concept of fashion for fashion's sake.

• Shop around. Hats look great in the hat shop, especially if you've got expendable cash burning a hole in your pocket. But a hat can look very different out among the masses, so take your time and choose something that you're likely to wear more than once.

• Match your personality. In general, Prince recommends looking for a nice flat cap and avoiding anything with a peak or with writing on it. But you have to think about your own personality and sense of style, and try to find a hat that matches. If you're a T-shirt and jeans kind of guy, a zippy felt hat is not going to transform you into a zoot suit swinger. In other words, you should never buy a hat that's "too cool" for you.

• Be trendy, but not silly. There's no getting around the fact that a man's hat is an affectation, and it's going to call attention to the man who wears it. And in many cases, Prince says, hats can just look silly. So avoid the haberdasher's hard sell, pick out an understated hat that fits who you are, and start looking retro—and ahead of the trend—at the same time!

For more information on men's hats, check out the following organizations or websites:

The Hat Bible: History of Hats
www.hatsuk.com/hatsuk/hatsukhtml/bible/history.htm

Hat Life Online
www.hatlife.com/pages/home.htm

Hat Center
www.hatcenter.com

Rick's Hat Check Room
www.reiss.dk/hats/default.htm

HatHatHat: Hat Links
www.hathathat.com/links.html