Investing in a new watch

If you want to invest (i.e. get your money back and maybe a small profit if/when you decide to sell) in a watch in that price range you have to go used. If searching for 1 watch b/w $1500 and $2000 I'd look at a used Rolex Air King/Datejust, Zenith or used Omega Seamaster/Aqua Terra. If looking for 2 watches with the same amount of money I'd look for a vintage Air King (throw it on a leather/croc strap) and a Seiko SKX007 for a sport watch.

A Sinn 556 would be a great choice in the $500-$700 range (used).

If you must go brand new I'd look at a Sinn or Stowa (I don't care for Stowa but it's about as good as you can do brand new in your price range).

Stowa Marine. Best $700 I ever spent

Edit: be prepared to wait months for it though. They are worth the wait!

Try a second-hand Grand Seiko or the Omega Seamaster as suggested above as a place to start and see comparable watches that you would like.

Look at something from Oris - they have sporty to dressy and everything in between. If you don't get a chronograph, it should be well within your budget - even at full retail.

Chris

Disregard watch, buy $3k worth of shoes.

I kid, I kid.

I would save it up. It seems you think people are shallow, but I think you'll find most people to be fairly considerate and understanding.

If anything get a name brand on that wrist for under $1000 (eg: Lower end Movado) and use the rest for a nicer suit, maybe go bespoke.

You can probably get a brand new Omega Speedmaster Date (older style but still in production, non-Coaxial) for a little under $2,500 from an AD. Skip the Omega boutique, though.

Assuming you're going to improve the other aspects of the wardrobe and want a watch that will go with an officer class wardrobe, the vintage Datejust would be an ideal choice. I'd try to find one with a white or silver dial, the linen dial if possible, no two-tone. If buying new you can go with something like an Omega DeVille or similar. Seiko and Orient make great watches which complement business dress, and are priced well below the range you specify so you could save some money.

The above assumes you want to go for a classic seamless unified business look. So many people now want big watches, and it's become acceptable to wear sports watches with business dress many places, so something like a Seamaster pro, Speedmaster mid size, Heuer Monaco, are par choices. Sinn watches are in this range and tend to be seen as cult watches. Sinn does make a classic dress watch but it seems stodgy to me. A Sinn U1 is a great, distinctive watch but will dominate the impression you make when worn with a suit.

Since you will be in the tech industry a complication watch would not be seen as out of place. Sinn does make a Flieger with a light dial if I remember correctly. That might give you the best of both worlds.

I think the only real rules here are: not too big, no two tone or loud colors, respectable brand(known for making watches and nothing else), no goofy or ostentatious self descriptions on the watch face ( this rules out new Rolex, etc.).

As you will be entering an MBA program I'd recommend Vanguard TSM and buy a g shock with the remainder.

Save up and get something in the $5k range at least if you're trying to make an impression.

Anyone who knows watches will know what you're wearing. Those who don't won't be able to tell if you bought a fashion watch for $200.

Actually, the vintage Datejust isn't a bad idea. You can also pick up a nice vintage Cartier tank vermeil that will give you some panache.

If you want a simple dress watch, why not one of the Zeniths? The stainless steel Ultra Thins should fall within your budget...

This is a bigger waste of money than a $5000 watch.
The $2400 Zenith looks like any $50 watch and there is no brand recognition.
Probably has poor resale value, for that reason.

I agree--a Zenith Ultra Thin would be an excellent choice. Not the most outstanding movement, but understated and well-proven.

You are an idiot. Lets be honest, everyone has seen your posts about watches and we are all aware that you really don't think they are worth the money. If he is thinking about going into management, it would probably behoove him to not walk in with a rolex. Brand cachet is not everything. I think that a Zenith Ultra Thin is understated, elegant, and all around a great watch.