I have narrow ankles and I prefer a tailored fit, which makes it challenging to find ankle boots that fit well. I have become quite intolerant of the “stem in a flower pot” visual effect of my own ankles in booties when the openings are too wide. The visuals below are good examples of boot openings that look overly wide on the ankles, at least to my eye. This is definitely a personal preference.

Free People Westmont Heel BootFree People Aquarian Ankle Boot

I showcase the entire boot by wearing them with flared, straight and skinny cropped pants and jeans, or with skirts and harem pants. This makes it all the more important for the tops of the boots to fit closely around my ankle. These visuals are a good example of how I like my own ankle boots to fit.

ISABEL MARANT Etoile Deyis Leather Ankle BootsAlexander Wang Kori Booties

I have become a bit more accepting of a wider bootie fit on my ankles when I wear cropped flares, straights or culottes (see the pictures below). The wider hems of the crops seem to complement the larger bootie opening, which offsets the “stem in a flower pot” effect a little. It’s NOT perfect, and getting booties that fit more closely to my ankles (like in the pictures above) is absolutely first choice. But since I also have fussy feet, I will make the compromise.

In fact, I just did so by committing to Calvin Klein’s Narla booties. They don’t fit nearly as widely on the ankle as the examples below, but not as closely as I would like either. As long as I wear them with cropped straights and flares, culottes, or full-length flares, we’re good. I will not be wearing them with skinnies, skinny crops, skirts or dresses.

Free People Insider Step Fray Crop JeansGOLDSIGN His Boyfriend Cropped Jeans

Over to you. Do you have narrow ankles and find ankle boots hard to fit? How tolerant are you of gaping around the ankle when the bootie openings are wide?