If you had $250 to spend on a watch...

Vintage Omega. I picked one up for $200 and I get more compliments on it than any other watch Ive owned.

Vintage Longines, far sexier than Omegas

I'd probably get a Tissot PRC200.

I faced a similar debate around this time last year. Ultimately, it came between Victorinox Swiss Army and Hamilton. I chose the the Victorinox because it had a white face. The Hamilton Khaki was a close second, though.

Touché my friend. Although I havent ever seen a decent looking one for less than $250.

Are there any vintage Omega or Longines you can get at that price in a size bigger than 33mm case though?

I got mine on ebay about a year ago. I see a lot of them going for 200-300 on there.

Here are some ebay links for some nice Longines watches. http://cgi.ebay.ca/VINTAGE-LONGINES-...item19bc2f58bd http://cgi.ebay.ca/Vintage-Longines-...item1c126ea37d http://cgi.ebay.ca/LONGINES-RARE-SOL...item1e5be5c5a5 http://cgi.ebay.ca/ORIGINAL-MEN-LONG...item4aa1074eab http://cgi.ebay.ca/1959-STUNNING-VIN...item3a5af720f0 The third and fourth links in particular are very nice.

I've had a Hamilton Khaki for the last three or four years, and it's a great every day watch. Simple, stylish and built like a rock. I've dropped it on the floor more often than I'd like to admit, and there's hardly a scratch. Their leather bands (with nice contrast stitching) are very thick. Mine shows little wear. http://www.classybrand.com/watches/w...-H64451733.asp

Vintage watches can be great value, but keep in mind the (likely) cost of an overhaul.

I think for $250, I might go for a vintage Mido Commander for around $100, and spend the rest on service from a trusted watch-servicer. Mido uses top of the line (not in-house) movements. They're great value for the money in mechanical watches--aesthetics are subjective, of course.

For new, I think I would look to Seiko, Citizen, Tissot, Hamilton.

The best outcome for the OP might be to either luck into a fantastic deal for a titanium Seiko Samurai, or to up the budget a tad and luck into a good deal on one (probably gently used). Those are nice watches; I wish I'd sprung for one back when it was possible to find the orange Ti Samurai on a bracelet. I'm not a big fan of the stainless sammies.

^+1 Some people recommend going vintage without considering the fact that the OP knows nothing about watches. Cherry ain't ready to pop yet.

Hamilton Khaki King, I guess, if you're not going vintage. I think I paid around $250 for that.

Are there really any seiko's that are at the $250 line? Most of the Seiya stuff that's worth getting (6R15 movements) seems to have a new price of $330 and up; conversely, most of the Seiko 5 sports stuff can be had for $100~175 on the grey market. Maybe the Samurai, Sumo or Knight (iirc, not sure on the models) are some Seiko diver models worth having, but I am not sure where they are priced at.

For some reason I actually get a lot of complements for my Seiko Sea Urchins; they can be had for $100 to $135, with a little bit of work.

Dive in, the water's great!