Can't help you with the under $500 but appreciates thing really, but here's just one of many watches that meets your criteria except that it's $200+ more than your budget. So in a nutshell probably no help at all. You could get a vintage Omega Geneve for around $500 but they're more on the dressy side.
http://www.jomashop.com/hamilton-watch-h35405741.html?utm_source=googleproduct&utm_medium=cpc&utm_campaign=googleproductsearch&pt_source=googleads&pt_medium=cpc&pt_campaign=(ROI)+Shopping+-+Sale+Watches+$500+-+1000&gclid=Cj0KEQjwlLm3BRDjnML3h9ic_vkBEiQABa5oedUK_5Ih oh8mdOQPMKo1mnGVkwyESzxoplGkN6nst8IaAmdx8P8HAQ