Thank you all for your candid opinion. I'm in the military so I'm trying to get my fashion sense back lol. More to follow.
You have an understanding of what works for your body/skin color in terms of colors and shape and you definitely have a sense of style but I think your next step is putting the pieces in your wardrobe together correctly. Your first pic was nice, but since the shirt had so much visual interest, the vest became just too much. That same outfit with a solid shirt works or that smae outift vestless works (although I am not a vest guy so I would recommend vestless all the time). In this outfit, while the tie is not to my taste, if you want to wear it, since it is a bit loud, I would not wear it with that sportcoat. The only real "issue" that I think you have is your pants. You should hem them a bit shorter (these are fine, the first pic are too long). You could also go for a somewhat slimmer pair. It looks like you have a big upper body and probably don't want to look so top heavy by having slim pants but you can do a bit slimmer, which I think will be more in line with the shape of your jackets. You remind me a bit of Tiki Barber and he is a good template for bigger guys to look at in terms of dressing for that body style, leaving your wife for a young blond is optional.