Hamilton seems over your budget, so, if you don't mind a "clomage" watch, San Martin has great-quality versions of the Tudor Ranger and the Hamilton Khaki Field for less than $270 - they contain the NH35 automatic movement. The Hamilton clone is the SN0137-G for only $158 and has a sapphire crystal with AR coating (which Hamilton sadly lacks), is 38mm, and has a great-quality nylon strap that looks as good as Hamilton's (I don't have this model, but did get a couple of the straps, which are great). I do own the Ranger clomage, SN0107-G, which was surprisingly-good quality - there are several variations in colors and even a higher-beat SW200 (ETA clone movement, making it a little more expensive) - in 38mm or 36mm, AR coating, $268, and a great steel bracelet that I switch out with the above nylon straps made for the SN0137-G (and one-pass straps from Crown & Buckle).

I have two Hamiltons and, while they are better quality and I really like them, it frustrates me that this homage company beats them in some areas, like AR coating, and is significantly cheaper.

If you're looking for something similar to a black gilt BB58 without being direct clomages (like me), Glycine has 2 Combat Subs - the GL0484 in 42mm (available at Gnonom Watches) and the GL0401 in 39mm (at the European Glycine store online). There is also the GL0261 with its vintage style Arabic numerals.

I have the Glycine Combat Sub 0416 - it is my beach and swimming watch as well as one of my toughest all-around watches. Came on a bracelet, but I prefer it with several different single-pass straps. With 200m of WR and at 42mm, it is big, very legible, and tough - perfect for swimming.

Tempted to buy a Steinhart, but couldn't get over their comic-appearing crown. Felt like I'd seen it before, then it occurred to me what I was remembering...

They are very versatile - beater, swimming, or dressed up. Here are my two 42mm Combat Subs.

Dress, casual, field, even pilot watch. Change the strap, the Murph fits most all occasions.

I'm now defending clients in criminal cases, but was once upon a time a prosecutor. Not sure whether jurors really notice watches and don't see many on them, like most folks these days. I pick the watch that goes with the suit. So I'd probably do the Bambino with black shoes/belt and the Hamilton with brown. But any of yours could work well (except the G-Shocks, IMO). My theory is that those jurors who like watches will notice and appreciate when you're wearing a good one and wearing it well. Shows thought, organization, and preparation. That gives you credibility (and that is gold in the courtroom, as you know). I think what can hurt, possibly, for a prosecutor since you are a public servant, is an ostentatious piece (jurors who notice, being taxpayers, might think their taxes are aren't being wisely spent). I do know a prosecutor that sports his rather blingy bluesy Rolex for all to see and, even though I can appreciate it, I wouldn't think it plays well to a jury. I personally like to wear my Hamilton Murph during trial - looks nice and can be appreciated by those in the know, while not being just a status flex.

Good luck in the trial and let us know how it goes.