|Jil Sander, $1253|
Luckily my favorite boot company Frye satiates my craving for those simple details. The Jackie Button boot just oozes commitment to classic. A pull-on style with decorative buttons on the pull on tabs make this boot workable, wearable, no muss no fuss. I'm more than willing to shell out $347 for them, but won't even have to do that, if you're lucky you may find them still on sale for $295!