Something dressier, still rugged and the definition of a tool watch. Go sieko, maybe a Turtle (SRPJ35) with a metal band it can be as dressy as you want or as rugged as he will need. Keep the military style watch as a second watch for all the farkles, he desires outside the office.

I would get a decent Seiko or even an orient Bambino for the office and pick up a Garmin instinct, or Suunto Core for when he’s outside of his 9-5. You could easily come up with a combo of two watches for 500 or a little more that would be way better than one watch that really doesn’t do any of those things great. Check r/watchexchange for some deals on used watches. I would advise against trying to get all those features in a nicer watch. He’s not going to need a barometer or compass at his desk, and he’s not going to need a dressy watch that he’s worried about messing up while he’s doing more rugged activities.

Seiko Alpinist.

The only watch that would meet those reguirenments is one of the ana-digi (analog dial with a small digital display) Casio protrek models. Or maybe one of the smaller digital ones like with a metal bezel the prw30.

These have a barometer with weather alarm, compass, altimeter, thermometer, and the PRW models also have atomic radio sync (not satelite/GPS) if you are within the range of the Colorado radio signal, most of the US is), the PRG models don’t have atomic radio time sync. They are all solar watches (battery is charged by light)

The models with a stainless steel bezel look less toyish so those are probably the better choice.

Don’t get stuck on the rubber straps, you can get a Nato leather strap for it or some other leather strap if he realy won’t like it.

Timex has the expedition north tide temp compass (that’s the actual name) models but these are missing the atomic radio sync and the barometer. They do however look less sporty and come on leather or bracelets options.

The only satelite /GPS casual watch I know within budget would be the citizen satelite-wave but this one doesn’t have the other outdorsy features.

The citizen altichron is another option that has an altimeter and a compass but I don’t think it has a weather alarm if that’s important. It might also be more complicated to use compared to a protrek since it’s analog only.

Apart from the timex all the others here are big watches.

There might be some smaller protrek models like the prw50 and prw60.

It’s an odd combination of features for a more formal watch, most watches only have the practical features like solar charging or atomic sync but no other outdorsy features. For something like this you could look at Casio’s edifice line and get one of the atomic sync or Bluetooth sync models. Also an eco-drive diver from citizen would be a good everyday durable regular watch.