Looking to get my first dress watch. Is a black dial appropriate for business? Can the strap be black or brown?

I took some pictures wearing sweat pants with my suit jacket to play around with the rise of the trousers. I point to my naval for reference. Pic 1 is around my hips where pants typically rest on my torso Pic 2 is me pulling them up a bit Pic 3 is wearing them on my natural waist Pic 4 is pulling them up as high as the pants would allow I think pic 2 and 3 look best. Appreciate any insight!

First time getting a MTM suit. The stylist suggested this shade of gray and with a shorter jacket to give me better proportions. For reference I am just under 5'8", slim but a little skinny fat. I think I have disproportionately short legs compared to my torso. For comparison, I've attached some pictures of an off-the-rack suit from Brooks Brothers that I had tailored recently. To me, the MTM looks baggy in the midsection and is too short, and I thought the Brooks Brothers suit looked good. Am I crazy?

Last night, my 16 year old son had a huge win. He passed his FAA written exam and is only a few steps away from earning his Private Pilot's License. I am truly thankful to @Antonio Centeno for his part in making this night very memorable for my son. A couple months back, my entry was selected for the Citizen Promaster Skyhawk watch. As I mentioned in my entry, my plan was (if I won) to present it to my son when he passed his FAA exam. Last night he got his big win and an incredible watch. It didn't dawn on me until two days ago that the Skyhawk is the name of the Cessna 172, which is the first plane he ever flew at the age of 14. Again, a huge thank you to Antonio and this amazing group of extraordinary gentlemen (and ladies too).