Thanks for the suggestions! I actually started the trend of wearing shirt stays around my area. I have a guy I get them from on Amazon, and they are so cheap I just buy several pairs at a time. My shirt is always tucked in with no issues, and always looks sharp. I wear wool socks all year round and they usually go all the way up to my knee so that is never an issue for me, during the winter I mostly where my long legged under armor (thermal or summer ones depending on what I'm doing that day).

I do find that boot cut jeans fit me quite well in a size up, for regular ones just don't. I'm going to be visiting the Mens Wearhouse down the street from where I work to see what they can conjure up for me.