These look surprisingly awesome with a pair of Levi 501's and during my senior year, they became the "it" thing to wear. Some kids wore the cheaper, generic brands, which just didn't get the job done. My sweet mama dropped about $80 on Christmas Eve of that year to buy me the name brand boots that I desperately wanted. When I wore them with my straight-legged Levis, which had also just become an "it" fashion statement in my school (I LOVED the preppy era), I felt very cool and I strutted my stuff with the pride of a peacock. lol I miss those boots in the winter. We have never really had the kind of weather that requires such a severe boot but that was never the point to wearing them in the first place. It was all about having that preppy, John Denver snowy mountains loving image and that is an image that will always speak to me. If I weren't sadly much too heavy to fit into a pair of my beloved 501's, I'd buy another pair of these and wear them every fall and winter from now on. There's just something about that gorgeous brushed leather coupled with that magnificent red shoe string that sets my heart aflutter even now.