I was going to do a post about how cool ring boots are and how surprisingly hard I imagine they would be to pull off. As an example I was going to post this picture:
After digging this picture back up, I realized Stevey McQueen isn't wearing ring boots. He's wearing some sort of moccasin that looks vaguely like a ring boot. Now that that idea is in the dumps, I'm going to rant about how ring boots can be worn wrong.
Ring boots look good when you've got some skin in between your trouser and your boot (so rolled trousers for those who couldn't figure it out). They also look good when the pant cuff sits on/around the ring. They look silly when you've got a pant opening so big that it floods over the boot and parachutes about your leg. Being a moccasin, this shoe will look and fit smaller on your foot than most shoes, so pants that look okay with other shoes may look baggy with the moccasin ring boot. For most younger men, baggy pants isn't the look you're going for. If you're older, you probably don't wear 511s-514s and wouldn't care to wear some ring boots anyhow. Ring boots really aren't that practical and if it's your first boot, I'd just get a desert boot; they're cheaper.
This is my hundredth post. Kinda' anti-climatic huh? Photos jacked from Inventory.