this is what 80 looks like.

bay area style icon raymond holbert has kept a daily journal for 57 years—and here are his words of wisdom.

Good morning! A week ago, I posted a preview of today’s newsletter on Notes and it blew up. It lit a fire under my ass to write the thing…so I’m typing it up right now on a flight sitting next to a very serious looking couple reading magazines side by side (The New Yorker for her, The Economist for him). Enjoy.

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I met Raymond for the first time last year, backstage at a fashion event in the San Francisco Ferry Building.

He was wearing a dress shirt, corduroy pants, and a vest adorned with dozens of decorative buttons—all in earthy shades of green and brown that looked like a page out of the Frog & Toad picture books. He wore a camera around his neck with a posture of quiet confidence; I knew he was a photographer or artist, something like that. Most noticeably, he was a much older man in the sort of social space that skews young.

I just remember thinking, I have to meet him.

I shimmied through the humid backstage chaos to introduce myself. He was easy to talk to, with a genuine smile that crinkled in the eyes. I learned that he had been doing fashion photography (among other artistic pursuits) for decades.

Our conversation was very brief because well, everybody loves Raymond. Everyone knew him, wanted to say hi and chat with him. As you’ll soon learn, he is a beloved local figure, a fixture at every local arts event. The Bay Area’s very own Mister Rogers meets Andre Leon Talley.

Months later, we crossed paths again. This time, at a fashion talk at the Legion of Honor (the theme was “Female Dandies”). I gasped when I recognized him in the crowd, in his element with a camera. “It’s Viv from the KQED fashion show!” I chittered excitedly, unsure if he remembered me. He said he did.

We talked for longer this time, and discovered we had a lot in common. We both spent our childhoods in Oakland and Alameda. We are both water signs (he’s a Pisces, I’m a Scorpio). We both love fashion and swimming. We both identify as anthropologists in how we approach our respective art practices. And we both live in the same neighborhood now. He gave me his business card before we went our separate ways into the shimmering crowd.

I emailed him last week on a whim, asking if he wanted to get lunch after his morning swim.

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Which brings us here: Raymond and I sitting across from each other, empty lunch plates pushed aside, talking about his journal.

We talked about the Met Gala, Black dandyism, the heyday of downtown Oakland department stores, San Francisco vs. New York in the 70s, the time he met Bill Cunningham, online shopping, maintaining quality of life in old age.

Initially, I thought I would write about our conversation in a Q & A format for this newsletter.

But it felt scattered. It was missing the through-line that mediated our real life conversation: his extraordinary journal. As I asked Raymond about his style sensibilities and trend cycles through the decades, it always came back to his lived experiences, documented daily without fail for 57 years in his journal.

That’s nearly 21,000 days.

My big ‘aha’ moment from our lunch was that journals are a better window into someone’s personal style than their clothes.

You see the context of a person’s life laid out before you, how they think and feel, the daily minutiae they deem significant enough to record, their handwriting. This conveys more about true style than an outfit of the day photo dump. Perhaps there’s a lesson here for the Gen Z fixation on “achieving” personal style, or the Millennial cottage industry of “3 word method” style worksheets.

If you want to feel good about your personal style, don’t overthink the clothes. Start keeping a journal. You’ll learn way more about your self-expression and build a personal archive of invaluable memories.

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Below, I break down Raymond’s approach to journaling.

*Images all shared with his permission.

• Raymond originally started his journal in college, using it as a “date, tax record, phone, and scrap book.” He believes that the longer journals are maintained, the more valuable they become to your loved ones, especially “after you exit this life.”

• Just as there is no one “correct” way to have great personal style, there is no correct way to journal. It looks different for everyone, but the best ones always exude the unique beauty and creative expression of its creator.

• Want to buy the same journal Raymond has? Because we are in the middle of a calendar year, you can either get the un-dated version of the journal to start whenever you want, or order the 2026 version.

Now let’s take a tour of 10 things Raymond likes to put in his journal. Get ready to be deeply inspired…

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1). Weather Report

At the top of each page, Raymond writes a brief description of the day’s weather in his signature bubble letters. In this April 1st entry, he wrote “RAINY.”

I figured the weather played a factor in the following lines, which read “SWIM? no! the chance to sleep in.”

Raymond goes to the pool three times a week in the early mornings. He spends an hour in the dive tank doing mobility exercises. He tells me the objective is just “not to touch the walls.” This keeps him spry in body and spirit.

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2). Ticket Stubs

Here is his ticket for the Ruth Asawa exhibit at SFMOMA. I also saw the show recently and wrote about what people were wearing there.

This summer, he will visit his daughter in New York to see the Superfine: Tailoring Black Style exhibit at the Met. His favorite Met Gala look was Colman Domingo’s long blue cape, a nod to André Leon Talley.

“I do think I have a little bit of Talley in me,” Raymond mused, recalling his journey as the first African American instructor hired at the San Francisco City College art department in the 80s. He later served as chairman of the department, and was inducted into the Smithsonian Institute of African American History and Culture for his contributions to the field.

Despite (or because) of these achievements, Raymond maintains the belief that there is “no limit” to what he can learn in his life.

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3). Data Visualizations

Raymond saw this bar chart on demographic trends in a newspaper and found it interesting, so he saved it in his journal.

This is a reminder that any information you read in newspapers or magazines can be made personal, and become a part of your archive.

Notice the things that make you go hmmmmm.

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4). Restaurant Menus

A Chez Panisse dinner is usually a special occasion—I wish I had saved my menus from the two times I have eaten there. Menus tell the story of how we dine. You have a record of how much a little gem salad cost, what kind of produce was available, how many courses were served.

Just as my generation looks back on 1950s jello shrimp cocktail recipes as a nauseating culinary crime, I wonder what kids 70 years from now will think is more shocking…the fact that we ate protein bars named DAVID or the fact that sushi still existed??

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5). Memorabilia/Artifacts

This is a band-aid from the 1980s designed for Black/brown skin tones that Raymond found in a box of things that were “bequeathed” to him.

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6). Scientific Diagrams

Raymond has had many friends develop Alzheimer’s. “I don’t have it yet, but I think it is probably forming,” he says. Throughout our conversation, I get the sense that he thinks a lot about the value of memories.

“There’s this song that plays in the back of my mind often these days. I Can See Clearly Now, by Johnny Nash, you know it?” Raymond asks me. He sing-speaks the first few lyrics of the song.

I can see clearly now, the rain is gone

I can see all obstacles in my way

Gone are the dark clouds that had me blind

“I really see things more clearly than I ever have. I understand things better. I see why things in my life had to happen the way they did, even if something was traumatic at the time, I see how it fits into the way my life unfolded,” he explains.

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7). Brainteasers

Staying mentally sharp is a priority. He saves these Hocus Focus “spot the difference” puzzles and tests his friends with it.

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8). Photographs (of “friends, lovers, relatives, and enemies”)

There are countless faces in Raymond’s journal. And not just those near and dear to him. If you have crossed paths, even briefly, there is a chance you will make a cameo. On the left, a photo of models from a local fashion show. On the right, a photo of Raymond with his son.

And here’s a street style moment:

There was one page that stood out to me because it had a mug shot of someone on it. Raymond, perhaps picking up that I was curious but did not want to pry given the gravity of the subject, explained that it was a photo of the man who killed his friend’s son years ago. “I put it here, because this was the day he was released from prison,” he continues.

A journal reveals the web of how many lives can be impacted through a person’s actions, good or bad.

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9). Appointments

Towards the end of our lunch, Raymond shows me how he journals in real time. He flipped to today’s date—May 7th—and writes in bubble letters: “VIV CHEN MEET!” next to a business card for crystals.

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10). Birthdays

For every single journal entry, there is a list of significant birthdays listed at the top. Raymond asks for my birthday and jots my name into the October 26 page along with Bootsy Collins, Mahalia Jackson and Domenico Scarlatti.

“You’re in good company,” he laughs, adding that he has always gotten along well with Scorpios.

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After lunch, we had a mini photoshoot together…

Thank you for sharing your wisdom with us, Raymond! You can find his work on his website MEMORYBANQUE.

xo viv

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Thanks for being here. You can find me on IG and TT. My wardrobe pieces and recs are saved here—unless it’s vintage, of course ;)

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