This guy (and the guy below) know what they're talking about. Orient makes awesome dive watches, and their 'Bambino' collection is suitable for business wear. High-quality, affordable automatic watches. Look for deals on Amazon, Jomashop, OrientWatchUSA, or Ebay (I've never tried Ebay but assume it would save money). Orient is a subsidiary of Seiko.

Seiko 5 refers to a 'movement' within a watch. It is a workhorse automatic movement (automatic > quartz, more complicated movements are more desirable for no reason but that's just the culture when it comes to watches) that seiko uses in tons of watches. A watch with a Seiko 5 movement will be a good watch a regardless of which watch you pick, so just find one with the proper aesthetics and you'll be golden.

I'm not a fan of Timex, I find their watches to be way too loud. It sounds insane but Timex noise seems to always amplify once you're trying to get into some deep work or trying to go to sleep. I had to wrap mine in socks and put it in a drawer to get to sleep until I eventually returned it.

I also rock an $11 digital casio quite often. The battery has lasted several years, it keeps perfect time, and it adds a level of hipster irony that us millennials love when juxtaposed against a suit and wicked expensive shoes.

Nothing short of everything will really do.
 

While I am going to blatantly disregard the title limitations in my recommendation, the Tissot PR100 in silver for $325 fits really well in pretty much any situation. Here's a picture of it. The crystal combines well with the silver making it look even better in person.

I personally would stick with a classic silver look with a watch that maintains a relatively normal size. You can't really go wrong with that style and can end up with a watch that looks much more than its worth.

 

Try out Corniche ... small watch maker from Sweeden. It will set you back around $300 but well worth the price - very stylish, formal and elegant. Google "Corniche Watches"

 

Timex T2M708 ...looks great and mine has been down 110FT and still works, been down below 60 many times. I could easily buy something very high end at this point but don't because of this baby. Don't try to get some clown brand that nobody has heard of. You're not fooling anyone.

Overwhelming grasp of the obvious.
 

This Wilk Watchworks company seems to be using Chinese movement - in terms of look, I am not a fan - I personally think that they are fairly cheap-looking (of course, this is my opinion).

Most quality watches with complications (i.e. tourbillon, moonphase, etc) will have a way higher price point. Overall, I would advise you to stick with strong brands and to avoid the "new brands" - you will likely get bored after a few months

If you want a watch with a tourbillon like these I can highly recommend you some models from Tissot (very good value for money), as I have seen a few nice ones with this feature; you get a Swiss-made watch from a respected brand, with a timeless look.

 

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