3 Keepers & a Regret: Sari Botton

Leaving New York, keeping everything.

Sari Botton of Oldster & Memoir Land

3 Keepers and a Regret is a recurring series on Retail Therapy on Substack where I ask people I admire to name 3 things they’d fight to keep — bought, inherited, stolen — and 1 thing they regret.

I’ve been a bit obsessed with Sari Botton for more than a beat. I listen to podcasts where she’s a guest and have bought her latest book more than once. What I didn't expect: all the ways she's still a New Yorker. Even though she doesn't live there anymore.

You may know Sari from Oldster Magazine. I’m a reader and fan. I love the variety of voices and journeys. How we all eventually get “there.” But I struggle. I can’t even accept that the term “middle age” applies to me. My therapist insists it does.

I first came to know Sari through her Memoir Monday roundup from Memoir Land. It’s my favorite email. I carefully work my way through, savoring each piece slowly throughout the week. I’ve been a subscriber — my first paid Substack, actually — since Jan 2023.

On a whim, I asked Sari to respond to 3 Keepers & a Regret. When she said yes I “eked” out loud. Radio tilted his head in a funny way, so you know it’s not my common noise.

Three Keepers

3 things you’d fight to keep — bought, inherited, stolen

No. 1 — NYC subway token

My NYC subway token, from the 1970-1980 series, which I wear clustered with other charms on a chain around my neck. I left New York City for the Kingston area 21 years ago after my husband and I got kicked out of our under-market loft in the East Village. Yet somehow I still think of my life upstate as "a temporary living arrangement."

In 2013, when I published the first edition of my first NYC essay anthology, Goodbye to All That: Writers on Loving & Leaving NY I bought a bunch of these tokens on eBay, had a jeweler friend drill holes in them so they could be worn as pendants, and sent them to all of my contributors.

I may no longer have a place to live in NYC, but you will have to pry this token — and my permanent status as "a New Yorker" — from my cold, dead hands.

Sari Botton's 3 Keepers & a Regret

No. 2 — Charlotte Stone’s multi-colored shoes

Charlotte Stone's multi-colored shoes (each shoe in a pair is a different mashup of hues) have been following me around the internet for years. I've wanted them badly, but most of the time they had chunky wooden platform heels, which, thanks to serious arthritis and five compressed disks in my spine, are not good for me in my 60s, and weren't good for me in my 50s, either, when I started seeing them. But recently I saw this low pair of their sandals, with a squishy, comfortable footbed, and even though they were a splurge for me, I had to have them. I was so happy to discover that they are incredibly comfortable. I am going to be wearing these all summer. Get ready to be sick of me in them; I don't care.

If my great aunt Lucille were alive, she'd try to steal them from me, like she did with the shoes I wore for my bat mitzvah.

"These look better on me," she said when I woke that morning and found her prancing around my family's living room in them. "You can wear my shoes."

I made a deal with her: When I outgrew them (they were a size 5 and Aunt Lu was tiny), they were hers.

If great aunt Lucille were alive, she’d try to steal them

No. 3 — CK for Calvin Klein denim skirt

The CK for Calvin Klein denim skirt with kick pleat that I bought at a stoop sale in the East Village in the early aughts, that I wear to death all year. This skirt is my best second-hand purchase ever, and I have a million of them. I think I paid $4 for it in maybe 2002? It has always fit me as if it were made for me. I can wear it year-round—bare-legged in the summer, with tights in the winter—and I absolutely do. At 24 years and counting, it doesn't show its wear. And it's a good thing, because I don't know what I'd do if it got too threadbare for me to reasonably wear. It's my most reliable wardrobe staple. I hope I have it (and suspect I will) for the rest of my days.

Best second-hand purchase ever

One Regret

now the regret

My high-ish-heeled No.6 shearling clog boots. This was not the first pair of No.6 shearling clog boots I'd bought barely used on Poshmark. No, this pair I bought after I'd realized I could no longer wear high heels, nor wooden-soled clogs. ((Read Sari’s take on her clog transition.))

I bought them already knowing I couldn’t comfortably wear them, nor the two other pairs I owned, one with a much lower heel, the other with a wedged heel. It was wishful (read: foolish) thinking. I just loved the way they looked so much, and ignored the voice in my head that said, “Really??? Your aching back would like a word.”

I have given away almost all of my wooden-heeled clogs, and for some reason I can’t part with these, even though I don’t wear them. They were a waste of $150 (used—they were like $500 new). And now they’re a waste of my limited closet space.

The regret taking up space in Sari's closet

Why I'm Still Shopping

I fully respect Sari’s ability to commit to her regrets. I have a closetful.

That we can leave somewhere, yet still belong. And why so many of us try to fight our own body to hold onto our identity, no matter the pain.

And then there are those Charlotte Stone shoes. OMG I want 3 pair. I was only going to allow myself to buy one, but it’s sold out in my size. And yes, I already contacted the company, in case.

So I’m learning from Sari and not settling for second best. I’m waiting for the perfect pair.

Thanks to Sari Botton for a fun read. Check out Memoir Land and Oldster.

When life stops making sense, we shop. More soon.

Rani Monson