I have watches reserved for yard work and going to the gym (and working on cars, etc.). That's the advantage to an, ah, extensive collection. My preferred workout watch is a Swatch Sistem 51 that I bought at least ten years ago while in Switzerland. And my preferred mechanic/yard-work watch is a Seiko quartz solar-charging quartz watch.
For me, it's fun to optimize my watch for where I'm going. Going to New York where I'll be window shopping at watch stores? Ulysse Nardin Marine Chronometer, my highest-end watch, thought both the Zenith Captain Chronograph and the Cartier Santos will also serve to attract the staff and provide me the privilege of trying on watches I'm not willing to pay for. Going to Pierre, South Dakota to facilitate a workshop with state employees? I'll wear my U.S. Government Marathon GSAR on a rubber strap. Or, if it needs to be dressier, a Seiko Presage automatic with the midnight blue enamel dial. Or really any of my vintage watches from the 50's through the 70's. Going to DC to meet with the bosses? I'll wear an Ebel--sufficiently obscure to avoid the appearance of pretense while still being obviously nice and respectful. Going to a meetup with other watch collectors? How about an enormous, blingy Concord C1 in black nitrided titanium and rose gold? What about an NAWCC regional? For that, a ca. 1946 Jaeger-LeCoultre ref. 2953 in 18k gold--nobody else there will have one of those and everyone will be interested.
Usually, of course, nobody notices or cares, but hey it's my hobby, not theirs.
Rick "who can wear a different watch every day for two months without repeats" Denney