Three classes of watches worth having in your wardrobe:

Sport
Casual
Dress
Sport watches could your basic Timex Ironman watches or even smart watches. Useful for training.

Casual - LOTS of options here - field watches, pilot watches, divers etc. I favor a good dive style watch

Dress - minimalist and sleek - thin case, leather strap
What you end up spending for each piece is entirely up to you.

There are good options at tons of different price points.

Most people are not going to be dropping $50K on a Patek Philippe
Just keep in mind you never want to wear a sport or casual watch with your nice suit...even though you see James Bond wearing a diver with a tux.
Oh, and oversized watch trend is dead in the water.

Wear something with a case size in proportion to your wrist.
Nice infographic here from Real Men Real Style:
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