Are these enough in cold weather (under 20 degrees?) for about 20 minutes outside at a time?

These pants aren't lined, however if they are wearing the proper winter attire, this pant should be fine. Victoria- LT Apparel

Can you wear boots with these pants?

Yes. I would think so. They are not like joggers.

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French ToastBoy's Pull-On Relaxed Fit School Uniform Pant (Standard & Husky) School Uniform Pants

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