This isn't something that I've ever done, and I experimented with it a few times last weekend. I recently got a pair of Wolverine 1000 Mile Winchester boots, and unless I do something to shorten my inseam it just looks like I'm wearing wingtip dress shoes. I like a little boot to show when I sit down. Do any of you do this? Am I totally missing the mark here? For the record, I DON'T do it when I wear the boots to work. I just wear a pair of slim dark jeans and don't cuff them at all. I kinda like the cuffed look on the weekends though.