Honestly I think the pink would draw more attention than the size of the watch in that example. Most people aren't paying close enough attention to others' wristwear to notice size.

I think there are certain traditionally "masculine" things that would draw more attention than others if a woman wore them, but I'm struggling to think of any that would cause actual upset. You still hear the occasional grumble about women in business suits from time to time, to spite women's cut suits having been a thing for decades, but that's mostly well accepted now.

Tuxedo, maybe? They cut them for women too, but that one feels like it's mostly still in the male category because its opposite is often expected in certain formal settings. A women showing up to something formal in a tux and not a dress would probably still do it today, depending on the event and the people in attendance.

Like imagine a ball or some other bougie shit where a husband and wife both show up in tuxes.

Bro I see girls with short hair wearing boots all the time and nobody bats an eye. The second a dude in a dress walks by everyone stares and whispers. There's worse things that can happen to a guy in a dress than weird looks too, and I'd wager they're more likely to happen.

They became "unisex" (often still labeled men's clothes and on men's section of the store) because so many women used them.