Hey there toots -
I haven't worn jeans and tall boots together - but then again, I don't wear jeans when I ride either.
You don't have time at all, to run into the washroom and change? Could you change in the vehicle on your way to the barn?
If not, I would go with jeans and paddock boots n 1/2 chaps.
The issue with tall boots and jeans is that when you put on your tall boots - the jeans will bulk/bunch up - and make it uncomfortable for you. Tights, stay put and allow the boots to slide on and off with ease - jeans, not so much.
I can see it work if you have tight jeans and zip up tall boots - but pull on's might be an issue.
On the other hand, I've also ridden in jeans, half chaps, and shoes (shh!!!!! It's such a bad habbit), that doesn't bother me at all lol. It's kinda odd really.
There's nothing wrong with that :) Ariat actually makes running shoes you can ride it. So what :)
It doesn't matter what others think about how it looks - Go with what is comfortable for you!!!!