For me, it’s the Islander Northport. That seafoam dial is crazy cool, but my wrists are pretty small and I don’t know if I could pull off such an “in your face” type of watch. Plus, I tend to dress on the preppier side and I fear it would clash a lot with my style. But man oh man, if that dial isn’t sweet.
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Out of my league, both in price and in wrist size:
Oris ProPilot X Calibre 115
Ignoring price, wrist size isn't that limiting for me, but the intensity of the styling can be. There are a lot of beautiful green, blue, and red dial watches that I just can't see myself wearing. Same kind of applies to many dress watches and metal bracelets. I think they look really nice, but they just don't quite work for me in practice.
Cartier.
Love 'em, but I'm a grebo biker so not sophisticated enough to pull it off - but can enjoy the brand vicariously through my Mrs (Ballon Bleu)
Bulova Lunar Pilot
A Rolex GMT Master II, any reference really.
Rolex Day-Date in yellow gold. I think it's the hefty gold President bracelet that would overpower me with excess flash and symbolic bulk.
Brew Metric. Love Brew watches but they’re just too small on me :(