I actually get peppered with this question quite a bit. Honestly, it is always awkward. I have an obsession with all things mechanical. It started with vintage cars, evolved into motorcycles both vintage and new, and eventually came something mechanical that was slightly more portable....watches. I'm in the military. Everyone I work with knows what I make. We all know what each other make. But with that being said, there is a great discrepancy in how we manage our money and what we choose to spend it on. I am by no means wealthy, at least not by my definition. But, my wife and I manage our money so that we have money to spend on things we enjoy. Some people don't get this concept.
I certainly have a collection that is not inline with my income bracket. It came from a lot of saving and a lot of planning. I'm not ashamed of it, and I wear my watches for me. But inevitably, somebody will notice them. My Oyster Perpetual and my Transocean get the most attention. These are watches that most non-enthusiasts will recognize. Normally, the first comment is "Nice Folex," assuming it is fake. Apparently, I get a look of disgust on my face whenever someone talks fake watches. Probably because counterfeits really piss me off. Nevertheless, the next comment is either "Where did you get it?" or "It is fake, right?" If they ask where I got it, I just tell them about my favorite AD. If they question the fakeness, I tell them it is real, and try to leave it at that. But the third question is always "How much did it cost?"
I normally try to deflect the question. "Not as much as you might think. I like to buy my pieces pre-owned" Maybe a "I try my best to forget that number." Normally those provide enough pause for me to redirect the conversation.
However, a lot of this has changed what I wear, and for the better. I purchased the Rolex and my Breitling very early in my collecting days. Now, I'm rather bored with them. I would not buy either of them again. However, the fact that they draw so much attention has made me wear them even less. So these days I find myself more attracted to watches that are off the beaten path, and not recognizable by the masses.
For instance, I bought a Vulcain Cricket GMT this year. Even most WIS have never really seen or fondled a modern Cricket. It normally goes unnoticed when I wear it, unless I happen to walk into a higher end watch store, in which case it draws a crowd. Last May, I was at JFK getting ready to fly to Moscow when guy waiting at the gate walks over and says "Excuse me, sir, this is an awkward question, but is that a Cricket?" What followed was probably the most pleasant exchange on watches that I've ever had. The guy was wearing a very nice JLC Master Calendar, which happens to be one of my grails, and we spent a solid hour talking watches. It made me forget most of my bad encounters, at least for a bit.