Angie's advice is so wise (natch--haha!). Tall boots ARE hard to fit. Feet are hard enough, but add calves, and you've got a double challenge!

I let go of one pair of black tall boots that I loved a few years ago, and I actually don't miss them, because I kept a pair that is identical in olive (Donald Pliner, Devi 3). They are probably my most-worn tall boots now. I also have a tall black pair with an equestrian vibe (Blondo, Volly), a stretchy pair with narrow heel (Donald Pliner (Nikko) that I like to wear for as a pump substitute in winter, and a flat pair of brown ones that lace up the back (Sofft, Sharnell), which I was thinking of donating--until brown came back this year with a vengeance and I started having some current things I might wear with them again.

All of these boots are comfortable, and I would like to wear them more than I do. But I don't miss skinny jeans and pants, which was what I wore them with the most at one point. Skinnies were too tight on my calves. I have a couple of pair of slim straights that I can tuck into boots, but I rarely wear them that way. I'm more likely to wear tall boots with dresses, and I just don't wear dresses all that often. I'm intrigued by the suggestion of wearing them with shorts. I have some long shorts that I can envision trying with tights and tall boots.