A 28, especially in two tone, references the 1980s for me, which was the watch of that decade. Smaller watches, like smaller bags came back into style a few years ago, in reaction against the previous trend for larger sizes that spanned many years. But, the pendulum is slowly swinging back again to larger bags and watches. IMO, a Rolex is best known as a man’s tool watch, so I prefer a mens rolex (I have watches of all sizes from micro to oversized (Cartier, Rolex, and a variety of other brands, and I also dip into DHs watches: Rolex coke; breguet, JLC, IWC, since these days he only wears Alange watches). But, I define classic, in this thread, as the one watch size that can withstand trends for women, so I picked 31.
ETA:
@Mini M , I view the majority of Rolex watches as riffs on a metal band tool watch, so to me, they technically signal ‘day’. I often wear ‘day’ watches for evening and vice versa, so to me, the size to day/night distinction blurs. If someone has a very small wrist, the classic should be what looks most appropriate, to scale, and is comfortable. I am 5’2”, size 38 chanel, 49 Dior, 34-38 Hermes, US designer 6. I am medium boned, and I think of myself, as being on the chunky side of slim relative to the very slim/petite true size 34s on this forum, so I probably skew larger than most re watch face.
Nothing beats trying different watches on in real life. Take action shots both close up and full length of you wearing different sizes. I try to wear the same thing (black v neck sweater, charcoal gray pants when trying on jewelry, and take an action shot from the same distance and angle for ease of comparison). No jewelry or watch store has ever questioned my need to take a pic in order to ‘see’ what I look like.
have fun deciding