My Footwear Lineup: Boots, Wedges, and Court Shoes

Vivienne Westwood for Melissa

Surprisingly comfy!

I got rid of all my high‑heel stilettos about six years ago. Gave them all to my nieces (they were over the moon; I only bought designer shoes). It was a gradual withdrawal, so at the point that those shoes that couldn’t be worn for more than 15 minutes, that’s when I knew it was over. I still kept a few wedges (including a fabulous pair of Vivienne Westwood red wedge heels) because they make me feel fancy and keep me around eye level instead of staring into someone’s navel at a party. They’re still wearable, but the days of excruciating pain in stilettos are long gone. I’m genuinely happy they went to a good home.

Join Me Weekly in the Slow Lane

L’INTERVALLE

Love their boots.

I’ve always loved high boots, not high in terms of heels, but high up the leg. They hide the baggy knee wrinkles, they’re comfortable, and they go with just about anything. I’ve always been a sucker for black leather. And I love the clunky look too; those boots have personality while still being relatively flat. They make me feel grounded, confident, and like I can walk anywhere downtown without needing to “just sit for a minute.”

As I get older, I really have to be thoughtful about what I wear on my feet. Comfort and fashion do not have to be mutually exclusive, and honestly, they never should have been in the first place.

And now there’s pickleball. Since I play a lot, I’ve had to pay attention to what I’m wearing on the court. It wasn’t until I bought a pair of new court Mizunos that I realized just how HUGE the difference is between pickleball shoes. I didn’t last an hour before my dogs were screaming to get off the court (anyone a size 6? ). That was the moment I understood: this is not a sport you can fake your footwear in.

The shoe has to give a lot of support and actually perform, but I still care about how it looks. I’m not ready for anything that screams “orthopedic emergency.” I want something that lets me move, pivot, and not roll an ankle, but also something that doesn’t make me feel like I’ve given up. I’m willing to invest in this shoe. There will definitely be a future post on pickleball fashion, because that’s a whole category of its own.

Getting older hasn’t made me less stylish, it’s just made me smarter about what I put on my feet (and body). So instead of trying to fight the “cute” stigma I carried around for most of my life, I’m finally embracing it. If my shoes want to be practical and adorable, who am I to argue?