I've had quite a few nice classic cars, and a few nice classic watches. Funny thing is, I always make money when selling!
My Breitling Navitimer Cosmonaute I bought for $1,600 and sold it a couple years later for $3,450, if memory serves me. Would be worth over $5K now.
I sold various Rolexes, including the one I inherited from my dad, and made money. Sold an early Heuer (pre-Tag), and made money. Still have a Tudor Homeplate Chrono that I'll be selling soon, and a couple of old Panerais, which I will probably keep. None of these watches will get cheaper as time passes by.
Is a fancy watch needed? Of course not! Neither is a Tesla or even Nissan Leaf. It's just that we all have things we like, value, and enjoy.