Digital Timex Indiglo. I find I’m not smart enough for analog time. For some reason I can’t just glance at an analog watch and know the time, I have to think about it. And an analog watch with no numbers on it? May as well strap an aquarium to my wrist - something that might be nice to look at but offers no time-telling capabilities.
Right now I’ve got a cheap Fossil stainless-steel (colored) pocketwatch chained to my belt loop. When I’m dressed up I don’t wear a wristwatch as I wear custom-made dress shirts and I don’t like shredding the cuffs.
When I’m being casual I alternate between a Timex Indiglo Twist-n-Set and a plain black Swiss Army watch.
All of my watches are analog, and I’m a guy FWIW.
Zap!
Incidentally, it’s very un-hip to wear a Rolex. But I do it anyway.
Seiko Chronograph. Analog, three teensy dials (stopwatch winute hand, main time second had, alarm), and a big second hand that starts, stops, and spins all the way around in under a second on command.
I had a Vostok self-winder for a while, but one of the little clips that holds down a gear inside broke :(. I’d like to get another. There’s just something incredibly nifty about not needing batteries, and the Vostok submarine Amfibians are nifty-looking. And waterproof deeper than I’ll ever go. 
I collect watches so it’s always something different. Right now I’m wearing a Seiko, self winding diver’s watch.
Gotta side with Rhubarb here: I really dig gadgets. For the last few years, I’ve worn a Suunto (Finnish, but marketed in the US) watch that has a digital thermometer, barometer, altimeter, and compass. I have to admit that the gadgets go unused 95% of the time, but it has been mighty useful in the field at times, and I like the understated black frame and band. Also, it’s a very large watch, and you know what they say about the size of a man’s watch…
…Oh, wait, that was hands. Damn!
I have a Citizen Eco-Drive (Solar powered).
I like Quartz watches (although even though I’ve not been around for twenty million years, I’m sure I’ve had Quartz watches that lost more than a few seconds, despite all of the claims you hear), but I’ve found that every quartz watch I ever owned died shortly after having the battery replaced. So I wanted one that wouldn’t need a new battery and I couldn’t afford the Seiko Kinetic.
Hexagonal 2-tone Cartier Santos. Nice watch, but my Seiko kept truer time.
Got a Casio backpackers watch. First one I bought about 10 years ago, and I upgrade every few years. Now it’s got an electronic compass, altimeter and temperature. Next upgrade will include the GPS positioning device. That will be awesome. Only thing is that the dang elevation is for wooses, 'cause it maxes out at IIRC 6,000 meters.
I normally don’t wear a watch, except when I have to wear a suit. Then I wear an analog. Its a silver Fossil Chronograph that looked really cool when I got it, before a realized the extreme crapiness of fossil watch quality.(long story)
I have a collection of Fossil stone-face watches that I rotate. I really like the stone faces, because then I never take time for granite.
Well it’s OK as long as you realize it…
Now when you’re ready to get of that toy and get a real watch… 
Lange
I carry a cheap pocket watch (Alba, I think?). However, like Narrad, I seem to depend on my cell phone more often. Personally I find a wristwatch very distracting (and yes I’ve worn them in the past - for extended periods of time).
I wear a Guess Waterpro that my wife bought me in the first few months of our relationship. It’s analog, blue shiny face, steel body and band, only numbers on it are the 60, 15, 30, and 45 on the body around the face (cuz when I’m going scuba diving I need to know how many seconds of air I have left, lol) and the date window. I don’t know how much it cost. It’s waterproof to 50 meters.
Timex analog indiglo w/alarm. Male
How do you tell if a watch is male or female? 
Tag Heur w/ leather band (don’t know the model)…it’s the Titanium looking one.
Longines, gold w/ lizzard skin black band
Seiko chronograph with sun/moon phases, white face and brown leather band.
I really need to pick up a cheap watch.
Johnny L.A…Rolexes are like the BMW 3 series now. Once, you were speshul, but now everybody has found a way to afford the entry level models .
For a Rolex to be close to hip, it has to be an old exspensive classic or a top o’ the line one.
I have a Storm. Analog, with small digital insterts.
If you’ve never seen this watch brand before, check it out; they’re amazing:
http://www.stormoflondon.com/
Analog, no numbers, white face, black hands, very discrete company logo. Dented, battered, worn, functional and refusing to die.
Given to me by the Danish network hardware supplier Olicom after severe provocation (I prominently wore a promotional watch from Bay Networks) The Olicom watch has outlived the company by about 18 months, now.
S. Norman