My cousin wore a Submariner for his wedding, my co-worker got married recently and her husband wore a Casio Edifice Chrono (white face). I think it's kind of cool that people are picking watches suiting their styles/personalities or have some special meaning to them for their wedding watches, rather than automatically picking a traditional dress watch because "you're supposed to" (not to shade anyone who does, I like dress watches a lot myself). 

Somewhere between A and B. Nature of the work is kinda closer to B but working in A sector. Still early in my career though, we'll see where things go

I'm kinda indifferent, but when it comes to automatics 9/10 times I think my experience with the watch would be better without one.  

I think when you're just starting out, having multiple cheaper options is better because it gives you a chance to figure out the kind of styles/designs/functions that you really like. The last thing you need when you start out is to drop a large amount on a watch and then realize you don't like it after a few months. 

Cop out answer but personally I believe the best solution lies somewhere in the middle. Maybe you could have one expensive watch and two cheaper watches. Gives you some variety in style and lets you switch out and have different watches for different situations. If you just have the one expensive watch, there's likely going to be some circumstance where you don't want to wear it, but still want something on your wrist.    

I don't necessarily match my clothes with my watches in terms of colours (though sometimes I do), but more the vibe/style of what I'm wearing. E.g. I'll wear my Seiko Tank when I'm in sort of business casual/casual Friday sort of outfit or my Timex Navi Worldtimer on a Nato when I'm in shorts and a t-shirt. Like you I also do consider activities (water resistance, likelihood of scratching, etc.), but since I'm fairly boring it's less of an issue. 

I like having variety, but I also do appreciate how good it feels when you save up for and attain that piece you've been looking at for some time. Perhaps some kind of medium? Maybe you can sell all but one Seiko and still get the Omega. e.g. keep one Seiko diver and sell the rest to help buy a Speedmaster, I feel like that's sort of a happy medium in terms of variety, but also getting that piece you've been eyeing. 

First: Casio Baby-G

Last: Vintage Omega Seamaster Cosmic 

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