Colours

Its all about attitude. Pier pressure is just your friends trying to control you. Wear what you like and beat your own drum. If your looking for fashion get a cheap tiffany as color style is a fickle thing. I change things up with cheap Nato's in many different colors. Let the strap match something not the dial.

1.  With the right band, yes.

2. If you like the color skip the Patek and go straight to the Pagani. Why wait until the moment passes? At some point we get old enough that we don't care anymore. There are studies that put that age for men at 47 (it is older for women).  So, cargo shorts, socks and sandals, and rock that Tiffany blue.

https://www.youtube.com/watch?v=2c-1eOzpS6o

1.  I tend to think black too casual for dress wear, but color alone isn't an answer. Blackface dive watch or field, whatever. One of those Movado museum watches or some other delicate gold cased thing, save till you're wearing real clothing.
2. Sort answer, no. It's not particularly more ridiculous than any other garish, er bold, color like orange. If it's the sort of color you'd wear anyway without the brand association, no harm, no foul, dubious taste. But really, for the next week ask yourself if you'd wear a turquoise watch with what you are wearing. After several fortnights of straight "hell no" answers, it may be time to reconsider.

Black requires more context.  Most Hamilton field watches I can think of are black faced as are most Sports rolexes.  If you can't wear an explorer 1 or a khaki field with jeans, I'm not certain what you might consider appropriate.

A strap change could be a difference.  Having worn a black dial watch for 40 days straight during the one watch competition, I have been pondering the various different characters of a black watch.

Example 

versus

versus

Who creates these rules??!  Like you can’t put a leather strap on a diver rule? I say wear what makes you feel good! Be free !! It’s just a watch after all…also as long as your wife/girlfriend/boyfriend likes it on you it’s even better… 😉

1. Yes
2. If you like it, sure. No need to wait. 
3. As one who doesn’t own a suit and dresses like a toddler, I’m not the best authority on arbitrary sartorial faux pas.

Having been a buttugly biker my whole life, I dont ever recall anyone giving me grief about the color of my watch face. Had they, I would have given them my full attention.....waiting for the laugh because it is obviously a big joke. I once rode with a guy named Tank....(use your imagination) He bought a fine horological classic the Tag formula 1 and proceeded to put it on a banana yellow leather band.  We all started call him Ronald.....he thought it was a compliment refering to Ronald Reagan......not Ronald McDonald. He died in a bike crash and never knew. We had clown red/yellow wrist bands made and wore them for a year. Wear what you want....life is too short.

I love 😍 that dial, reminds me of the vintage Atlantic Worldmaster.

Depends on the black dial:

This one is hard to pass off as casual - but that doesn't stop me - I use it all the time for travel as it can pair with smart casual and also easily slide under a dress shirt

This one is clearly a casual black dial watch

Something like this Timex Marlin with gold on a black crocodile strap just screams get dressed up

Wear what you like, but if you are trying to send a casual vibe then black dial, gold and fancy strap isn't going to get you there.

Great story,funny and bittersweet, when I have my first beer tonight I'll drink to tanks memory,your right life is too short.

Wear what you want with whatever you like, I've never run into the fashion police and I'm fairly sure that there is none located on WatchCrunch 🤣

I wear my Tiffany blue Sinn with whatever clothes I decide to wear, even my work clothes which are predominately orange.

And my black one with the same outlook. I don't care what anyone thinks, I'm definitely not trying to start any fashion trends, just enjoy my watches 💯

Black and orange works 😉

Depends on the watch IMO, butnof course you can! Do what ever you like 💪 I have a weakspot for people that can pull off G-Shock and suit or tracksuit and a small gold Cartier!! That's badass 😎

I consider black dial as a casual color. As said above it also depends of the watch. I can’t imagine a Submariner or Speedmaster is considered to dressy to wear with casual clothing.

Not even a Reverso is a misfit to casual clothing IMO

Nothing is true; everything is permitted.

Or at least wear what you want, nobody will say anything unless they are tactless or another watch nerd. 👌

Very much agree with @Ichibunz in that you do what you want to do. It's liberating to set yourself free of caring what anyone else thinks. 

Forking out € 30 k for a "Tiffany" Oyster Perpetual is probably not a very sensible idea. Suggest you consider the cheap and cheerful ISL-85. 

1% of the price, 80 % of the fun

When do you have time to model all of these watches? There is a challenge going on.

I think black dial watches are kind of like black shirts. Dressy compared to other colours, but not as dressy as white. Also surprisingly difficult to go full formal with it.

Old photo's my friend, some taken at work when I was there. I'm currently in the middle of a Workers Compensation claim so I haven't been at work for a week or so now, just resting up at home and spending all my time going back and forth to medical appointments 🤬 

Not you or anyone else will be catching me out that easily, come on, I may be old but I'm not senile 🤣 

I just wear whatever watch I feel like wearing.  I don’t care about colour or what else I’m wearing.  I want a watch that suits how I feel that day.

This is my response to both questions.