I’m a big fan of my Sinn 836, and it falls somewhere in that price range if you can find one. The Sinn 104 and 105 are also highly regarded tool watches with a small but very loyal cult following. They’re known for minimal design, feats of engineering and rugged utility, and the look of their watches really appeals to me.
Watchbuys is their US authorized seller and they have quite a range of features and colors.
Watches I don’t own but want to that would have been great to start with:
Certina DS PH200m - around $1000
Junghans Max Bill Chronoscope - a little over $2000
Oris makes some beautiful divers around that price range, tons of colors and designs and sizes.