But with such a bold silhouette, figuring out how to wear cowboy boots can feel intimidating. Should you tuck your jeans in or let them stack? Do they work with dresses? Can you wear them outside ...

And most days of the week, I'm in a pair of boots. They're loafers, tennis shoes, and slides all in one. I'll wear ... out as a little more fashionable than the next guy. The iconic cowboy boot ...