This is a great thread! I have several knee-high boots from FRYE and I wear them with skinny jeans so I couldn't tuck the legs in, but I loved the look.
I do have a question about the boots that are made specifically for horse riding that Jinete suggested:
How do these equestrian boots hold up to street wear? Can the sole take a lot of punishment or do they wear down faster because they're made specifically for riding horses?
My boots are very vintage and I don't wear them every day. However, they are holding well so far. When necessary, I'll take them to my cobbler for new soles.
I've been stopped more than once by an attractive lady and asked about these boots. Two even came up and asked if they could touch! Needless to say, these are among my favorites.