This fall, when I was in the midst of beginning a deeply satisfying Netflix binge of the dark, twisted, and amazing Jessica Jones, I found myself pausing an episode halfway in at a crucial moment. Patsy Walker, Jessica Jones's best friend played with full feisty feminist aplomb by Rachael Taylor, was walking across the screen with trepidation and the tension was high, but I could only focus on one thing — her perfect high-heeled ankle boots.
Maybe I'm especially strange, but for me, some sort of hunt for perfect heeled ankle boots is constantly in play. Great heeled boots are versatile ( you can wear them with jeans or slacks, or you can rock the with a sundress in the summer), fashionable, useful, and above all, comfortable. Comfort, after all, is the literal holy grail of shoe qualities. Once you find a perfect pair, my advice is to NEVER LET GO. Sadly, though my Jessica Jones-inspired quest for Patsy's heeled glory ultimately did not result in the identity of the pair she was wearing (it is truly my white whale...sigh), I have three pairs of perfect heeled ankle boots that I fully plan on continually getting resoled for all of time. My grandkids will wear these boots, gosh darnit!
Below, check out the rundown of my three much-loved pairs of heeled ankle boots, as well as the places you can get your own.
I bought these in 2013 and they no longer sell them any more so THANK GOD I got them in brown, black, and tan. My sister once borrowed my black pair and tried to "forget" to give them back to me so I had to hound her relentlessly until she returned them. I'm a good sister except when it comes to my ankle boots, okay? These are my favorites for their sturdy heel, comfortable fit, and casual look that also effortlessly translates into night time. But, because they don't make these lovely creatures anymore, here are my favorite boots below that will help you emulate the potential of this classic pair.
This is my boho version of the heeled ankle boot that I bought on a complete whim — I was running to an event and wanted to change out of my flats and Free People was just right there and so I took a leap. Lo and behold, now I wear these all the time (and bought them in slate as well).
The construction is such that the soles of these shoes are insanely comfy (seriously, it feels like you're walking on a foam mattress topper, in a good way), and the basket weave detailing means you can dress these up or dress them way way down. For example, I wore these to Coachella parties (don't judge me please) but I was also able to wear them to work events. They are all-purpose and I love them.
Here are some other, similar boots that you might love too:
These Vince Camuto showstoppers are ALSO boots that I bought while running to an event because my life is being perpetually late to things and shopping is always better in a time crunch. For this event, I ended up buying high heeled boots in lieu of heels, but ended up fantastically happy with that decision because these shoes are awesome.
They are the most formal of my arsenal, but they also manage to still be totally wearable during the day time. Also, given the new trends towards wide legged pants and 70s style jumpsuits, these shoes fit in perfectly with the trendy aesthetic while still leaving you able to walk around freely without your feet turning into painful messes.
If you're looking for similar formal ankle boots, check out the styles below:
photo credit: Nick Wiesner