I believe in the saying that men should only have two pieces of jewelry/accessory on them; their wedding band and their watch. No flashy gemstone ring or Ch@v-like chain necklaces. So spending £££'s on timepieces is actually not stupid or dumb.
If you're lucky enough to be able to afford classic high-end timepieces, they're like family heirlooms. You can pass it to the next generation. Just as one timepiece maker aptly says in its slogan; "You never actually own a Patek Philippe. You merely look after it for the next generation."
Most swiss-made watches retain some value as well so if you need the cash, you can sell it up given it's in good working condition. And as some classic models appreciate in value over time, the resale values can get quite handsome. Just imagine what a 1960's or 1970's classic Omega or Rolex would cost today.
First rule to remember, avoid watches with designer label names. Kenneth Cole, Armani, Lacoste, Pierre Cardin and the likes. They may make great fashion wear but watchmaking is not their strong suit.