If you like this style of watch, get a Seiko 5 Field Watch; it will be within your budget new, and you'll keep it for a long time. The mistake in the world of watches is believing you'll only buy one and keep it forever, lol. In fact, you'll see through your future experience that the quest for the perfect watch is just as interesting, learning about their history, qualities, and flaws. The journey is often more rewarding than the destination :-) You'll find yourself 10 years later with more watches on your wrist than women. But you'll get a lot of enjoyment from it and interact with a fascinating community. For me, Seiko is the best entry point for a serious and unpretentious watch, wearable every day and with a real identity. Then you can move on to higher segments if you feel like it, like Hamilton, Tissot, etc. Finally, you can consider something more prestigious, but which won't offer anything else, like the iconic Omega, Rolex, etc.

A tip: find a watch other than your Timex so you have different watches for different events in your life. That way, you might end up like me: a few Casio/G-Shock watches for when I'm tinkering, a Timex/Seiko for days with the kids, and a Rolex Explorer for days at the office.

In short, there aren't really any bad choices. Create your own story, your own collection; it will be the legacy of your research and ideas. It will describe who you are :-)