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someone reputable like Black Bough
Looks like a 1970s Longines 5 star ticks a lot of my boxes. Sleek enough to count as a dress watch (or is it?), but still utilitarian enough to also work with a three day stubble and a pair of jeans.
starfish&coffee-
That watch is really nice. I’m on a moratorium at the moment, otherwise I might have considered it. Love the dial.
The movement is also basically an ETA 2824 which are very reliable and still widely used, so parts and servicing will be easy to arrange and cheap.
Re: is it a dress watch - kinda not really, but in modern terms it pretty much is. A dress watch in the strict traditional sense would be more “elegant”, thinner case with thinner lugs, maybe made of gold or even platinum, not have a date, not have lume, possibly not have a seconds hand, not be automatic and probably not have a screw-down caseback or crown. In its day that Longines would likely have been considered a sports watch or general-purpose everyday “good” watch. The Rolex Oyster template, basically.
Nowadays most watches sub-40mm that aren’t field watches or out-and-out sports/tool watches get lumped into “dress watch”.
Regal
I added some links to my post ^^
All of those are in the 38mm range, which is a common modern dress watch size. Vintage is more typically 34-36mm. You don’t get too many modern mechanical watches going for that size now (unfortunately).
In terms of modern second hand stuff, I think the main thing to look out for is condition. Has it been taken care of. A Junghans Max Bill hand wound could be worth looking out for.
With vintage, buy the seller. It can be a minefield, especially on eBay - you need to really know what you’re looking at, what looks correct and what the red flags are. I’d buy from someone reputable like Black Bough for a first vintage watch.