DH always wears his boots, even on vacation. It is so hard to get him to wear tennies! Last year, he got stopped at every security check point we went thru. That was all he needed to make him wear his tennies, atleast on the way to and from vacation. I just put his boots in the checked luggage and have had no problems. I was even able to fit the hair dryer in one boot so the hair dryer had extra padding. LOL