I distinctly remember my first time venturing out into the world in high heels. It was in high school, and my best friend and I naïvely set out around Boston in our flared jeans and pointy-toe pumps. How we thought we would be comfortable spending the day in these heels is beyond me. I cringe replaying the details in my head. The more we walked, the more we began clomping around awkwardly to relieve the pain. In fact, at one point, we overheard two guys behind us snickering, only to have them outpace us and say, “Nice heels, ladies,” as they walked by. We caved and ended up buying some cheap white sneakers on Newbury Street to make it through the rest of the day.
Since then, I have never had luck with a higher heel unless I was wearing it to a sit-down affair or dinner. It’s a shame since I absolutely adore so many of the styles. Instead, I stick to shorter, kitten-style heels that are comfortable and walkable. Thankfully, the shoe trends have been in my favor, and the offering is plentiful—think slingback options, mules, strappy sandals, and many more. Ahead, shop 30 of my favorite heels under two inches of the moment.