Watches

i think anyone can pull off smaller watches, the problem is that you can't pull them off wearing casual modern clothing, i think modern shoes (brightly coloured, thick soles) especially do not work with smaller watches, if you wear simple clothing, casual but smarter than average, you can easily pull a smaller watch off.

take a look at these photos, all of them are wearing small watches, but they don't look out of place;

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you just need to wear clothes that are not obviously modern, and the same advice in reverse would apply if you were trying to pull a vintage suit or some other type of vintage clothing off: don't wear a massive modern steel watch, or anything too busy. it just wouldn't look right.