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What % of your watch collection contain hype pieces or are in high demand?
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Plenty of well kept older Omega watches available if you're patient with looking to buy secondhand.
In particular, I think the Omega Speedmaster Reduced II 3539.50.00 is particularly great. It doesn't have the 5 minute texts on each indices like most Reduced models do.
I would legit wear the shit out of a Rainbow Daytona if I had one. I was lucky enough to try one on in Tokyo at Nakano Broadway in late 2019. I don't have a loud/outgoing personality to match but fashion wise, I enjoy being unapologetically gaudy as fuck.
Personally, I tend to throw on a watch whenever I'm out of the house. Usually, it's to run a errand or to grab some food so I like to time how long it takes for me to get back home. In that case, a diving bezel to track elapsed minutes or even better, a digital stopwatch function for more precision.
I know chronographs can do the same thing, but I don't like to leave the chronograph running for over 30 mins when I'm not really gonna be looking at the smaller subdials until I get home.
I think the Seiko 5 SRPE57 fits the bill quite well! I bought this for my friend as a wedding gift. His work usually has him wearing dress shirts so I picked something that wouldn't be too out of place underneath a cuff.
As mentioned above, a day/date indicator can be quite handy. Only thing that would elevate it even further as a daily would be some type of quick-adjust for the bracelet.