I don't think the boots are high enough for a tuck. But I think either way they'd look better with slimmer pants. (incidentally, I am very much outside of the 'tuck is always terrible' camp. 'Visual disruption'? I don't agree that there has to be an unbroken line all the way from your dingus to your foot. A little military steeze never hurt.)
No you aren't. You just aren't comfortable wearing tighter/slimmerjeans. Also, having a small hem at the bottom of your jeans' legs doesn't automatically mean the rest of the cut is going to squeeze you like a sausage and bust your balls. Something like APC new cure might work for you.