I think it’s more about what you feel comfortable. For me I don’t give a shit what people think. I wear between 22 and 55mm, I had a few woman watches so I share wearing with my wife.

2mm vs 16mm

You can assess by two level of criteria l: Tangible: such as complex function, such as annual calendar, GMT, moon phase etc… Or practicability such as metal bracelet for all weather use, water resistance, power reserve duration… Case material such as rose gold, platinum etc…

Intangible: such as history, does this brand/model carry historical significance such as Santos Dumont or Fifty Phantom… Special numbers, is the series number same as my lucky number or birthday… Brand personality, such as if the brand concur with my values…

Mix: such as dial, design… these are very much subject to personal preference which there is no rules. Someone likes sundial and some like simplicity…

Recoil of seatbelt!

For the budget can I recommend:

Second hand Behrens Second hand Grand Seiko Second hand Ball Second hand Frank Muller