Russian P.M. Vlad Putin giving his watch to a confused child.

Men have few options when it comes to accessorizing, or at least fewer options than women.  We have even fewer still when it comes to jewelry.  True, some guys can certainly pull off earrings, bracelets (no, not Livestrong ones) or cool rings, but most men have problems making this work.  Also, stodgy old-guy sartorial standards dictate that a man's jewelry should be limited to a wedding band, a class ring, and a watch.  Since marriage isn't for everyone and class rings are only slightly better-looking than Sloth from the Goonies, wristwatches are the only basic jewelry that any guy can get away with.  

A great place to start is with getting a basic metal-band watch.  The beauty of these is that they can be dressed up or down; you can wear them with shorts and a t-shirt just as easily as you can with a suit, and you don't necessarily have to pull a Reservoir Dogs-style bank heist to get the money for one.  More formal options include straps made of leather or exotic skins like alligator or crocodile.  Animal-hide straps follow roughly the same rules as belts: the wider the strap, the more casual it will look.  Plenty of watches are made with incredibly wide leather but are very casual and shouldn't be worn for dress occasions.  More casual options include synthetic bands in fun colors.  Never wear a digital watch to any occasion that requires you looking dressed up, be it a job interview or a wedding.  Go with an analogue watch instead, meaning a watch with a face that has at least an hour and a minute hand.

Watch faces (the part you look at to tell the time) are offered in many shapes and configurations, so just try a few on and see what happens.  They can be circular, square, rectangular, and plenty of other shapes.  You may find a watch with regular numbers, Roman numerals, or no numbers at all.  Also, time isn't the only thing to be told on a watch.  Plenty offer dates, days, times in different time zones, and varying levels of water resistance.

Timepieces are sold in tons of styles at approximately a bazillion different price points.  While you can find a rather handsome men's watch at Kenneth Cole on Walnut Street, your best bet is to head straight to Macy's by City Hall, which easily has one of the largest timepiece selections in the city.  You can just as easily find a $75 Fossil watch there as you can a $695 Bulova.  If you happen to have gold bullion falling out of your pants (and more power to you if that's the case), Govberg Jeweler's has two Center City locations: Boyd's at 18th and Chestnut on the first floor and also on the Retail Level at the Comcast Center, Philly's newest, tallest skyscraper.  Govberg offers some of the most coveted names in the timepiece world:  Bulgari, Cartier, Breitling, Movado, Patek-Phillipe, and plenty more.  Bear in mind, however, that buying a watch this high-end isn't really necessary unless:

1. You'll be in a situation where a serious, tangible judgement call will be made on what you have on your wrist.
2. You're educated and knowledgeable about the intimate details of timepiece technology and construction (i.e. Swiss Movement, the affect of temperature and elevation on the watch's ability to keep accurate time, etc.)
3. You do, in fact, have the aforementioned gold bullion falling out of your pants.

No matter which type of wristwatch you decide to wear, if you pick the right one, it'll be a welcome addition to any outfit.  Go with what catches your eye and is appropriate for what you typically wear, and you'll be set.