I don't think anything looks better on a wrist then a classic watch. I didn't know this until I saw one on my own.  I got my vintage Omega from my dad. Actually, I found it in his workroom...broken...and when he told me I could have it if I could fix it, I didn't think twice.   He got it from his dad as a gift after his 1968 graduation from Notre Dame, and I loved it.  I brought it to a watch shop in LA, and after dropping more on repair than I ever had on all of my past watches put together, I was in awe.   Aside from the innate sentimental value, wearing it makes me feel powerful.  It is fun to wear to meetings, and I love the little ticking sound it emits.  I think it dresses up even jeans and a T-shirt, and I like that I feel like an adult.  Plus, its timeless, understated, original, and so F*ing cool I envy myself.