…as defined by this week’s Chewsday Challenge.
The problem with limiting yourself to one brand with a price ceiling is that few watchmakers offer much in style variation. To be frank, all Rolex watches look pretty much the same to me. And just offering the same watch with different face colors or metals (gold, steel whatever) doesn’t really qualify as variation, as such.
Vacheron Constantin, for example, has several lovely watch types and variations, but only if you’re not averse to having your nose suddenly start bleeding.
So here’s my choice of watch brand: Omega — specifically, these variations, all of which are available new, i.e. unworn:

I am somewhat constrained by my unshakable insistence on manual-wind operation, and it seems that for watches costing less than $25,000 (much less, in Omega’s case, bless ’em), there are precious few choices of brand. Sure, most offer many variations, except for that manual-wind thing.
Still, the above three are nice-looking and of decent quality, and I’d be happy to wear any one of them on my wrist.
Incidentally, if I were to go for used (secondhand [sic]), there’s always Patek Philipe:

…each of which is so beautiful they make my mouth water. I don’t even want to think what they would cost new — assuming Patek even still made them with manual-winding operation, that is.
And there you have it. My (post-Lotto) watch collection(s).
This one’s for Longtime Friend & Reader RandyGC (and all others of the Timex Fan Club).
There’s nothing — nothing — wrong with Timex. My only gripe is that the modern types are pretty much all battery-powered, which sucks. However, there are a few holdouts: the Marlin (not all variants, though), the Mk-1 (still in production!) and the “Worn & Wound” are manual wind operation:

Total cost of the set: around $700 (10% or less of any one of my choices, above).
I don’t care for the last one, myself — too cartoonish — but I’d wear the Marlin any day of the week, and if traveling to a place (e.g. Yurp) where times are frequently listed in 24-hour format, that Mk-1 would help out; and as an added bonus, would not be bait for the many watch thieves who infest cities Over There nowadays. I’d just have to lose that horrible canvas strap for a leather one (which would probably double the cost of the whole thing, har har).
My favourite. But then it was bought for me by my darling wife for my 65th. How could I not love it?
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That Timex Mk 1 looks very appealing.
I had that one, or a very similar earlier model, issued to me when I was on flight status in the 80s. Unfortunately they made me return it when I got a new assignment and came off of flight status.
I wear a old school Omega Seamaster my Dad bought new in 1956 that’s very similar to the white face one in the first pic. No date, just a second hand and a honeycomb face. It’s more of a dress watch than the later diving Seamasters. Went back to Omega 20 years ago and was completely overhauled. Auto though.