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I live in Hong Kong so I see a lot of nice watches here due to all the bankers, etc.
But there's always a little alarm bell in my head saying they're fakes.
For example, there was a young guy (20s) on the subway wearing a blue dial AP Royal Oak.
But his clothes were cheap.
Or I often see old guys wearing rolexes, but they don't care about their appearance (messy hair, etc.)
It's hard to know.
I think the reason I associate fake watches with people who dress shabbily is because in Asia that's usually how you spot fake bags - a rich woman who has an expensive bag won't be wearing cheap, ratty shoes. But maybe I'm wrong to apply that logic to men. We don't usually take care of our appearance to the same extent as women.
I saw Alan Sugar (Sir) in the lift at the Leadenhall building in London filming the Apprentice wearing his Rolex Daytona. Made me go and order one. Bet he didn't have to wait for years though haha

I was at my sisters wedding this weekend.
Aside from the "adults" it was all of her friends in their early 30's. (Full disclosure She is 31 and I am 30 and my wife is 28)
My wife was commenting on how stupidly dressed one of my sisters male friends was.
He was wearing a very slim, and very modern cut powder blue suit finished off with a pair of Vans shoes and no socks.
We both agreed he was a total douche,
HOWEVER, he was next to me at the bar at one point and of course what do I see...a Speedy Pro.