I like watches. I'm more of an Omega guy than Rolex, little less flashy for my tastes, but I wouldn't turn down a Daytona if someone wants to give me one.
I appreciate them the say way I appreciate pins really. Mechanical watches are a bit of an anachronism in a digital world the same way pins are in the age of flashy video games.
There are bargains the in the mechanical watch world too, you don't have to spend Rolex money to get a nice piece. But I treat spending money on a watch the same way I do on a pin. People who don't "get it" will give you a look when you told them how much you spent, but we know that the personal satisfaction and enjoyment is worth it.
There's no avoiding the stigma that comes with them, they're bling too, and they come with certain baggage. So does my car, but I drive it because I really enjoy it, not to show off. And in Southern California no one gives you a second look in a BMW anyways, they're like Honda Accords down here.