Now that winter's here, I'm considering getting some quality headwear. I work in a pretty formal office, but so far, I've resorted to throwing on a Phillies cap when going outdoors. Any suggestions on some proper hats? What should I be looking for? Frank D., Bryn Mawr, PA

There was a time when no man was fully dressed if he didn't have his head properly covered, when a hat was a sure sign of social position, and an uncovered head was an uncommon sight. An elegant hat meant that you had a surefire gentlemanliness about you. We would like to have experienced this long-gone phenomenon firsthand - we simply LOVE that old footage of every man on the street or at a ballgame dressed to the nines, topped off with a hat. Back then, it seems, everyone had style, and they all wore hats. The demise of all of this came in the 1960s, with JFK's lack of interest in them, and the onslaught of the hippie long-hair crowd.

Of course, none of this has anything to do with you and your Phillies cap.

Do us a favor - the next time you decide to put your cap on with one of your dressier outfits, please do so in front of a mirror. Either that, or ask the opinion of a trusted (but honest) friend. Not exactly killing 'em with this look, are we? There are two schools of thought here: 1) In the cold, any hat is better than no hat or 2) caps are generally for the younger crowd (read: boys), or for men while playing sports. Too bad for you that we agree with #2. Caps are just not to be taken seriously. If it were to be strictly a matter of function (warmth) over fashion (not looking silly), we wouldn't stop you from wearing one. But your cap is too visible and prominent be taken so lightly.

Hats are the one accessory that, if you are going to dare wear with a dressy outfit, should be thought of with extreme care. Not all hats look good, or even appropriate, on all people. Felt hats like Fedoras or The Trilby will somehow always be in style, but you almost have to be a certain age (say, 45) to be able to pull it off. And there's an increased chance that a youngster like you would seem pretentious and silly with one on. Wearing one of these "old-world" hats takes a lot of confidence and a certain dash. If you don't believe you can pull it off, then you shouldn't even waste the time to try.

If you must wear a cap with a dressier getup, you should consider trying a dark colored or black beret-style one, for that hip pseudo-French artist look. You'd be surprised at how acceptable these look with dressier clothes. A bit of caution though - if you are on the portly side, you run the risk of being mistaken for Sam Kinison with this look. You also might try looking into all-wool golf-style hats. These often have earflaps for warmth, and also look surprisingly acceptable on a young lad. Wool ski hats look best while skiing, and are not for suits and overcoats.

Finally, about that Phillies cap. The Phillies? We think that perhaps you're problem is not a lack of sartorial prowess, but rather that you are just aiming too low. Funny how Yankee fans never seem to have this problem.

Got a style question? Send it to us at comments@ffwdmag.com.