I'm looking to upgrade my wristwatch. I'd like to invest in something understated, masculine and classy, which won't look outdated in 10 years. And I'd like to keep it under $1500. Either new or vintage is fine. Thoughts?

Ebay's the way to go (make sure you deal with a reliable seller. Look for someone with a few hundred ratings and an approval rate of at least 97%). You can find vintage 14K watches for a few hundred dollars, or a used steel Rolex for less than a thousand.

Oris is a great brand. They use Eta movements and are very reliable.

Another reliable brand is Tissot. Tissot is owned by swatch group (also owns Omega).

Another place to fnd used vintage watches is http://mastersoftime.com/
- Thet restore vintage watches and are hit or miss. They were recently written up in the AMEX magazine.

I have a hamilton mechanical watch that I really like. They make some low-end stuff, but the mechanical is nice and solid. I beleive they are also owned by Swatch now. It a very simple stainless watch with a black dial; dial has a sweep second hand with day and date. There is a chrono that goes up to 12hrs. Perpetual motion with a window on the back to see the gearing. The company has some interesting history you can check out on Wikipedia.

Swiss Army makes some nice dive watches for well under 1500. Tissot also makes some lower-end pieces. Tag-Heuer is always a safe bet as well.

I got a Skagen watch for Christmas. It is super flat, very straight forward (without all kind of fancy functions) and looks quite good. The flatness is the best part though being about 5 mm thick. (1/5 inch)

http://www.skagen.com/item/233LTTM.fx

I've been a big fan of a lesser known watchmaker out of Japan called Android ( http://www.android-usa.com ) for some time now.

Most of their watches are in the $350-500 range and they've got some really sharp designs.

Personally I'm a bit of a gearhead, so exposed "Skeleton" watches like this one ( http://www.android-usa.com/2008/product_info.php?cPath=0_115_129&products_id=311 ) really appeal to me. Many of their models are also "Automatics" -- some brands call these 'Kinetic' -- that are capable of self-winding via a pendulum mechanism within the watch housing that draws energy from the natural motion of your wrist.

If you like smart, classy styling and the idea of never changing the batteries in your conversation piece/time piece then I'd urge you to check them out.

I have a Hamilton Khaki X-Wind Automatic. Swiss automatic movement. They have both Stainless Steel and Rubber bands and options for the watch color (black or silver). It's a large and heavy watch with a window in the back showing the movement. I've gotten tons of compliments on it and I would recommend it for those looking for a large automatic timepiece without having to spend the bloated TAG, OMEGA prices.

http://www.watchzworld.com/hamilton_khaki_x_wind_automatic_h77626153.html

To get a "real" watch, you need 1) automatic movement (as opposed to a battery-run quartz) and 2) swiss made. For understated and classic, I'd look for a diver watch, and I think the best deal out there on a name brand is the Tag Heuer Aquaracer. It lists for $1,800, but you can get it on Amazon for about $1,000. It's a substantial watch that'll last forever and, I think, looks great. Check it out at a quality jeweler... and then buy it on Amazon.

http://www.amazon.com/exec/obidos/ASIN/B000E3VJ3K/ref=nosim/uncrate-20

If you want a classy but understated watch, you might want to check out Sinn, a German manufacturer. High end quality and great styles - plus you won`t find people wearing it since it is rather a collectors` brand even here in Germany.
Especially like the lines 103 St (Chrono) and 756. Depending on the model, Sinn retails for about 1500 USD and up so it might be out of your budget. But who knows? Check it out:
http://tinyurl.com/ctr6c9

Tissot makes a good selection of classic timepieces in a variety of price ranges. They're classic Swiss watches and are a well-known and respected brand. If you're into chronographs, I'd recommend the Tissot
Le Locle.

I'll second the Tag Heuer Aquaracer. I have one (I paid about $1100 for it) and it's a classic Rolex Submariner-style look at 1/4th the price. The Submariner look will never go out of style.

If you want something a little sportier, check out the Omega Seamaster Pro as well.

Check out Stowa, they are cool and uncommon. They are German hand made watches, good quality for your money. http://www.stowa.com/

You should check out Kobold watch company. Watches made for SEALs and worn by actors & athletes.

http://www.koboldwatch.com/products/

Tsovet is a newer brand that has a great looking line. All of their models are offered in a variety of colors, and they are usually under $1k.

I like Rado's Ceramica line.
Perhaps this:
http://www.rado.com/en/Watches/Ceramica/Pages/ceramica.aspx?ref=156.0716.3.015

Nixon Rubber Player.

Also Bell & Ross watches kick ass.

Dont even think about it
Omega Speedmaster Pro, hasnt changed in 40 years, and still looks better than most others at even higher prices

I must second the Stowa recommendation. This is an old German watchmaking name with a young, innovative owner. You would be hard-pressed to find anything close to the quality, style and craftsmanship of the Stowa Marine Original for $1000.

$5000 - $7000 range: If you're willing to spend a little extra $$, check out ChronoSwiss. I really like the Chronoswiss Grand Regulateur.

$3500 range: Another beautiful classic is the Longines Master Collection Retrograde with Power Reserve (stainless steel dial with alligator strap).

$1000 to $1700 Range: For a more modest budget take a look at Baume & Mercier Hampton Square 8751.

If you want a watch that will last, be classy, and look good with anything, you need to get an automatic (self-winding) watch from a manufacturer with a good history and reputation. I'd suggest getting a watch on a steel bracelet, rather than a leather band, since it will look as good with jeans as with a suit. I'd recommend Omega, Tag Heuer, Sinn, Stowa, or maybe Hamilton (on the less expensive end).

My recommendation would be a lightly used Omega Speedmaster on a bracelet. This was the first (and only?) watch worn on the moon, so you know it's got a great story, and it still looks great today.

I for one love the watches by LÜM-TEC

Currently own the Combat B1 and have the M9 Chronograph on reserve which should be out late May or June.

The Movado Museum collection will never go out of style. The watches are very sophisticated, and they are always a conversation piece.

http://www.movado.com/Watches.aspx?Id=collectionmuseum

Check out ball watches in general. they are around the $1500 price point. swiss made, automatic, and they use tritium gas tubes for illumination (radioactive stuff) that always glows, meaning you never have to charge it with light.

I like the night train personally for that price: http://www.ballwatch.com

There are some great watches here, especially the Sinn, Oris and Lum-Tec. But my choice is Bathys. They have great Quartz watches, as well as automatics right around $1000. They have a FANTASTIC, timeless look. Comes with a deployant leather band and a rubber diving band (all in a cool Pelican case). Also, they have beautiful domes sapphire crystals. This is one of my fav's: Bathys AquaCulture.

I have had a Swiss Army for a few years and really like it. I recenlty got a Pulsar and I really like it. It's one that sets itself and all that jazz. They aren't pricey like some of the watches being named, but if it is quality and stylish then the name shouldn't matter.

I know it seems rather unoriginal which is what kept in off my radar for so long. But the rolex submariner date really is the ultimate timepiece. I recently got one and it is comfortable and looks good in any situation, plus it is built like a tank. I bought a 3 year old one and saved a bundle.

If you are looking in the under $1000 range I have an Oris and a Hamilton which are both great watches.

I have to agree with others, the Omega Speedmaster Professional is the way to go. Works with everything and I can atest with proper maintenance it will last forever. I wear my father's 1967 Speedmaster and get compliments on it daily.

I agree with Swiss Army. I'd been the Chrono Classic XLS Alarm and happened across a 40% off sale. Normally $695, so well within your desired range.

It's a beautiful, simple single dial (two hands on one) chrono with an alarm, something overlooked on many watches these days.

Chrono Classic XLS Alarm: http://www.swissarmy.com/Timepieces/Pages/Product.aspx?category=chrono+classic&product=241281&

Anything by Tag Heuer will make a classic statement, and is something you can pass down.

This one you can get from Moma store looks like an old Timex. I think it covers all requirements you had in your question.

http://www.momastore.org/museum/moma/ProductDisplay_Index%20Watch_10451_10001_43867

Tag Heuer Monaco. It's just a beautiful watch that has maintained its style for over 40 years, so no need to worry.

for simple classic quality i agree with the "go vintage" concept- i own a few old omegas and i love them, but my favorite is my Fortis they are the swiss made russian space watches.. hold up to anything and look great.

I really love my Swiss-made Hublot Classic. I have the stainless steel one (as opposed to the gold) because of my skin tone. It is not one of those big honking look-at-me watches that weigh down your wrist, rather it is thin, light, classy and understated. Watch people and non-watch people (women) pay my compliments on a weekly basis for its elegance. I have had the watch for decades and it is the only timepiece I think I will ever have. It has a quartz movement so it keeps time well, the band is rubber which feels nice. The band occasionally needs to be replaced if your skin has a lot of oils in it, but the watch store I bought it from replaces the bands for free.

I am a big fan of Invicta watches. They have some very cheap and some very expensive. I really like their Lupah collection, this watch is brilliant:

http://www.amazon.com/exec/obidos/ASIN/B0009P65ZK/ref=nosim/uncrate-20

It's a big solid watch that looks classy & masculine on your wrist. My wife loves it.