It's seems like no one here has worked in competitive high end sales where things like this matter. Sales is very different from other fields such as STEM / finance / IT and such, I need to make millionaires / billionaires trust me with their money. They tend to only want to deal with people they also view as successful / professional. The hipster with the Apple Watch is not going to get a single client, I know this because that's exactly what I have and was advised to stop wearing it because it looked unprofessional. Thanks for all the advice but based on the responses it seems like none of these watches can pass for a real one so this option wouldn't work for me. I'll look into buying an authentic used datejust or something similar.
To the person who advised me to get ahead first then focus on cars and watches, we just live in different worlds and you don't understand my field so your advice wouldn't work for me. Cars and watches are given away as prizes in competitions at my place of work to top sales people all the time. Once I get to that level I wouldn't need to buy a cars/watche and other luxuries because it will be given to me. The hard part is standing out enough to get to the point where they trust me enough to give me a constant stream of clients so I can start to compete at the top level. Also as I mentioned the car has already helped tremendously (surprise! millionaires are more trusting of someone that drives a new luxury car over a 1995 civic), I also dress, look and act the part now, the only thing I think can help me fit in more is the watch now.
It's worth noting also that I don't even care about luxury items such as cars/watches/clothes, to me they're just tools to get ahead in my field, the same way a carpenter needs to buy a hammer for his field. My end goal is to have a frugal retirement (somewhere between leanfire and fatfire) by 40 and all of this is just a means to an end. I don't really care for luxury items, for example I don't even use the Mercedes for anything other than work. My daily is a manual 2003 Mini Cooper that I prefer over the Mercedes any day of the week. The same thing is going to happen with the watch, I find watches uncomfortable and will not wear it for anything other than work.
Lastly I wanted to mention that it may be wiser to get information about peoples background before you blindly make assumptions. I'm in my early 30's and have spent most of my career in the engineering field where I made ~200k a year. I saved at about a 70% rate and can easily drop 15k on a Rolex if I wanted to be careless with my money. I'm not going to do that because as I stated before my goal is to retire by the age of 40 and it's the reason I changed my field in the first place. It seems like I was wrong in assuming this place would be filled with likeminded frugal people since it's a community based on saving money.
Once again thanks for the replies/advice everyone but I'll go with the used real option.