I am at a crossroads with my shoe collection. Aside from weddings, I can’t tell you the last time I wore a pair of heels in the last year. And yet, I own something like 80 pairs. Most of them still in storage from the move LAST October! And yes, I have plans for ridding my life of them. Interested?

This means that I’ve been rotating through my flats — a modest collection — and yet, none of them fit properly. Being comfortable has so much to do with well-being. Mood is directly tied to footwear: Flats for comfort, heels to make you feel powerful, boots to keep your feet dry, wedges to make you look like a dumbass when you’re tripping all over the sidewalk. Why else do we go shoe shopping when we’ve had a bad day, amiright?!

Seriously. I’ll pay ANYTHING to own a pair of flats that don’t tear apart my heels and inside of my foot or push on the outside bone near my pinky toe. (OK, probably within reason.) New Toms: terrible. I love my Toms wrap boots SO MUCH, but every time I wear the casual flats, I end up having to slip out of the heel and step on the back of the shoes for the remainder of my errands. Because, OUCH. This happens with SO many pairs of flats for me. The new slip-on Skechers I bought recently? Super comfy in the store, but ONE AFTERNOON of wear put horrible blisters on BOTH feet. Awful, terrible, bleeding blisters. Like, how the hell am I supposed to skate with open sores on my feet?! Strappy sandals are the worst — digging, rubbing, too tight… I refuse to wear flip-flops in the city, so don’t bother suggesting. I’ve tried brands like Mia, Converse, Chinese Laundry and BC Footwear.

Even wearing regular tennis shoes on a hike started rubbing rough on the side of my foot around mile 3. These were fitted by a shoe store professional, by the way. If you’re curious, even with semi-custom skate boots, I still have fit problems, mostly in the heel. It’s a never-ending battle with footwear.

Needs: comfort, support, prefer leather (so it’s something that will eventually mold to my feet AND hold up) — in a style that can go both casual-to-happy hour.

SEND HELP TO MY FEET, 30-somethings!

Drool over SHOES!!! with me on Pinterest.