I Walked 9 Miles in These Heeled, Knee-High Boots That Are Comfortable Enough for All-Day Wear

Despite being 5’9” and uncoordinated, one of my passions in life is wearing impractically high-heeled shoes. The main issue with this is not the inevitability of falling over, or even the unwanted attention that comes from collapsing in public, but the strain it puts on my weak, wobbly ankles. This being said, I’m not one to give up on my dreams, and have thus spent the last couple of years steadily building a collection of heeled boots that I can trust to keep me upright.

My Sorel booties and Jeffrey Campbell platforms rank among the best. However, I recently stumbled upon a classic pair I can walk in comfortably for hours: the Steve Madden Ally Knee-High Boots. Upon first glance, the primary draw of these shoes was their timeless silhouette. Hitting just below the knee, these leather boots look great over tight-fitting jeans and under wide-leg pants, and complement pretty much any length of skirt. They’re neither too chunky nor too narrow, and best of all: feature a nearly 4-inch-tall block heel that’s almost trip-proof.

Shop now: $142—$190; amazon.com, zappos.com, and nordstrom.com

No matter how uneven the sidewalk gets or how awkwardly I start leaning to one side, the heel’s thick, solid shaft compensates for the imbalance in weight. What’s more, the textile lining remains stiff from toe to ankle before taking on a soft, stretchy feel around the calf, a feature that stabilizes my feet and keeps my ankle from rolling. To really put these to the test, I decided to wear these boots for a Sunday of intense walking. At the start of my morning, I rushed two miles over a bridge to meet a friend, followed by hours of wandering from thrift shop to thrift shop until the sun set. By the time I got home, I’d walked nine miles without taking a single stumble.

To my fellow flimsy-ankled girlies who just want to be a little taller, I can’t recommend these enough. Shop them starting at $142 from Amazon, Zappos, and Nordstrom to give them a try.