Then it came to me— I’m sitting on a bench, processing my thoughts in the middle of the greatest city in the world, smack in the middle of fashion week.

This hasn’t always felt like the city of opportunity for me. It has sometimes been a city of exclusion, expenses, heartbreak, fomo, fake friendships, evil people and plenty of bad days.

It’s been a city where I worked minimum wage jobs to make it through college, the city where I failed to get many jobs, the city where I failed to launch an app and many different projects, the city where I had to break up with the guy I thought I would marry.

But also it’s been the city where I had the craziest adventures, met celebs, politicians and CEOs, threw parties at five star hotels, got to skip the line at many prestigious places, climbed successfully a very competitive corporate ladder, found my sense of style and self expression, started a business, had my first serious relationship and my first painful movie-type-like love, and paid more in taxes some years than my first full time salary.

New York is beautiful that way.

It knocks you down because it knows you’re capable of more. Then, it rewards you with a little art at the end for all of the trouble.

New York teaches you how to win.

So through all of the ups and downs, every time I’ve felt lonely, sad and insecure— all of the times I’ve felt like I had nowhere to turn… all of those times, I had New York and the endless familiarity of its streets.

And no matter what happens next, I know I will always hold my head up.

Because at least I don’t live in SF.

This isn’t my first store visit. This has been going on for months. It’s a real commitment issue. I haven’t bought a new pair in years.

Here’s the problem: I feel trapped between two extremes. Either I splurge on an expensive designer shoe or I settle for cycling through cheap dupes I’ll resent the second I slip them on. It’s an investment dilemma.

To make matters worse, I hate feet. Every pair of shoes feels extra sensitive, hard to get right. Certain shapes (open-toe flats) are simply not an option for me and never will be.

If I go for the expensive option, it has to be the pair. The kind of shoe that earns its rent in my closet. It has to work with jeans, slip skirts, mini skirts; through summer, spring, and fall. It has to work for family brunches, art gallery trips, city walks, photo sessions. And this is where the decision paralysis kicks in: there are so many designs here, but I can only afford one, so it has to be perfect for anything and everything.

And then there’s the trend factor. Take the ballet flat. It was the shoe of 2023-24. Every influencer had a pair, every brand released their version. But now what? Was it designed to last, or did I only like it because it was heavily marketed? The right shoe needs to outlast the hype cycle, work through every Instagram era.

If I go for the cheap version, I can relax on design. There’s less pressure. I could get a few pairs and experiment. Yet, I tried this through my early 20s and none of those pairs lasted or made me happy. Now I stop myself, imagining how much I’ll hate seeing the space in my tiny NYC closet filled with flimsy, torn up dupes. And if I have a rack filled with them, won’t I wish I had just one great Chloé or Prada pair instead?

And here’s the thing about quality: it matters extra because it’s a shoe. It has to sustain constant wear and tear, endless pavement pounding, and all kinds of weather. I’ve had bad shoes before. I’ve bought pairs that have hurt my feet. It’s not worth it.

Shoes are the piece that can either pull your entire outfit together or ruin it completely. The right pair fits in at a Fifth Avenue penthouse; the wrong one has you standing outside of Faena. Shoes are everything.

Of course, there’s the middle ground: Dolce Vita, Reformation and friends. Styles created for the trend at a price that makes sense. From my experience, they are not worth it. They lack the craftsmanship of true luxury brands but still don’t justify their price premium over the cheap dupes. As far as I’m concerned, they’re the same. And it makes sense why — Dolce Vita is Steve Madden backed, Reformation is private equity. There’s an incentive to skip out on quality. They’re made for trends, impulse, profitability and business ROI. The late night, insecurity driven, “checkout now” shopping habit. They’re the worst of both worlds; bad price and bad quality. But yeah, they look great on Instagram for the season. I just know they won’t work well for me.

So here I am, staring at strangers’ shoes in Saks.

There’s a philosophy to this. With a limited budget, do you invest thoughtfully into one or a few pieces that last over 5-10 years? Or do you spread it thin across many different designs? Personally, I find myself falling more into the former camp; but that’s what makes these decisions extra lengthy and extra difficult.

What is everybody else wearing on their feet?