What Steve Jobs, a Red Dress and Feeling Safe Have in Common

On dressing as an act of defiance.

Photo by Tamara Bellis on Unsplash

Yesterday, another writer here on Substack, Anne Kadet, tilted my world on its axis a few degrees.

I'm not going to cliff-hanger this one and make you wonder for very long what a woman could do to throw my universe off kilter. Let me give you a hint. It has to do with clothes. 

So Anne decided some 10 years ago–just take that in for a moment while you wait for what's coming. For ten years, that's 3,650 days: three thousand, plus six hundred, plus fifty more days, she has been wearing the same clothes. Okay, that's misleading, she's been wearing the same outfit.

In January, every year, she buys five to 10 of the same shirt, same skirt, same tights, she didn't mention underwear. Hmmm. Maybe she goes crazy and has fancy underwear. Something to think about. 

And then that's what she wears. Every. Single. Day. Until it gets too hot and then she puts on a tank top instead of the button down. All the clothes are black. Which she says means they all go together, but as anyone who's ever worn two different items of black at the same time knows, no two blacks are the same. Unless you bought a matching skirt and top and even then, not all bets are on. 

So brave, strong, maybe slightly OCD, Anne Kadet wears a black long-sleeved button down shirt, a black midi body-con skirt, black tights and black quasi combat boots every day. She says she hikes in this outfit. Does interviews in it. She owns one black bathing suit, one red dress which she says covers all occasions from weddings to New Year's Eve excluding funerals, but she has plenty of black for that, and one black sundress. Oh, and she has a pair of nude sandals for summer.

I am, in equal parts, inspired and horrified by this.

Partly because Steve Jobs did this, and then the infamous Elizabeth Holmes followed his lead. One of them no longer has to get dressed at all and the other is in prison serving 11 years for fraud. This should tell us something. 

I had breakfast with Steve Jobs and his daughter once. Okay, that's pushing it, but things happen in Palo Alto. If you don't live there, you just can't imagine. It's way better for stargazing than living in LA, where I saw not a single famous person in the entire two years I lived in Brentwood/Westwood. Also it depends on what types of stars you want to see. The Palo Alto version is decidedly skewed towards A) wearing the same black or navy or grey, functional clothes, always involving jeans and sneakers and never involving actual slacks (god that is just one of the ickiest words, slacks. Like moist or curd. Okay, I'm stopping there. You're welcome.) And B) loving all things tech. 

But back to Palo Alto and breakfast with Stevie. That was his favorite nickname. Can you imagine? No. Neither can I. 

There used to be a very popular, in-the-know little breakfast place in the Town & Country shopping center called Calafia. It was started in 2009 by Google's first executive chef, Charlie Ayers. Who incidentally was also the personal chef for the Grateful Dead. Do you see what I mean about Palo Alto? 

Back in 1999, Ayers got the Google gig by winning a cooking contest judged by Google's employees. All 40 of them. Where were the rest of us in 1999 when Google only had 40 employees, and why weren't we lining up to work for them? 

I for one was totally oblivious, happily unemployed, living off the profits of selling our first townhouse in La Jolla (Oh hindsight, why didn't you tell us to hold on to that little piece of property?) while building out our stock FJ60 Land Cruiser in anticipation of driving it through Central America. 

At Calafia, or any other restaurant, really, in Palo Alto, it wasn't that you expected so much to run into someone who was famous in tech, it just seemed to happen. So Steve Jobs liked Calafia and he ate there a lot. We did too, and one morning we were sitting at a table next to Jobs and his daughter. Ergo, breakfast with Stevie.

I didn't know Calafia had closed until I started to write this piece and had to look up the name to make sure I spelled it correctly. I know things change, but it's always a strange moment, that liminal space where current reality infringes on memory reality. You have to adjust what your mind sees to include the ending of something you thought still existed. It's as if a tiny part of you breaks off and floats out into the ether, still there, because you remember, but not there for anyone who doesn't. 

I like to daydream sometimes about places still being the same as the last time I experienced them. Of Palo Alto still being a small, wealthy but in an understated way, town, with Stanford as its biggest draw. 

A place where professors lived and the owner occupancy hovered around 90% rather than the 40% it is today. Something goes out of the heart of a place when not even half of its people live there full time and the uniform has changed from wealthy granola chic to urban founder grunge. 

So what of the idea of an individual uniform? 

For Jobs, at least the way he tells it in his biography by Walter Isaacson, he started out wanting a uniform for Apple. That proposal got him booed off the stage by his employees, but in the course of nurturing the idea, he became friends with the designer Issey Miyake and decided he wanted a personal uniform. In the book he tells it to Isaacson like this, "So I asked Issey to make me some of his black turtlenecks that I liked, and he made me like a hundred of them." Jobs noticed my surprise when he told this story, so he showed them stacked up in the closet. "That's what I wear," he said. "I have enough to last for the rest of my life."

If a famous designer custom made me 100 sweaters, would I wear them every day for the rest of my life? I'm not sure. Anne would, I'm clear on that. 

I've talked a bit here on Substack about clothes, my rather fraught relationship with them, about dressing for oneself instead of dressing for the occasion, which I think is a lot like learning to belong to ourselves.

For me, this is where Anne's plan falls apart. I am seduced a little by the idea of never having to decide what to wear ever again, of saving thousands of dollars a year, of being the kind of woman who doesn't care what she looks like. But back to the idea of belonging to ourselves, I want to wear clothes that speak to who I am, rather than who I am not. 

I'm not knocking Anne or anyone else who chooses to wear their own personal uniform, or someone who wears one because of their profession. That's not what I'm about. But for me, choosing to wear the same clothes, all in black, every day, would be a regression. 

When I was in sixth grade, I wore a white cotton skirt littered with tiny rainbow confetti polka dots and paired it with a white tee, striped vertically in matching rainbow colors. I thought it was brilliant. The mix of patterns, the connecting colors. Had I been 30 pulling off the same type of mix, someone would have stopped me and told me how great I looked. However, the 11-year old girl’s brain is fine tuned to singling out and exorcizing the outsider, the big thinker, the one who dares to do something that makes herself stand out from the others. 

It was Shelby, who would later try to befriend me when we ran into each other at UCLA, who started it. This was 39 years ago, so I don't remember what they all said, but I do remember making myself very small, wishing I were thinner and even smaller, hiding and crying behind one of the concrete pillars in the hallway between classrooms. I wanted to be invisible. I wanted to not be at all. 

That is the first time I remember that feeling. And it was just the first of many traumas at the hands of my peers. By my sophomore year, I’d stopped wearing colors and wouldn’t wear them again with anything nearing regularity for, so far, the rest of my life. I have one orange sweater, one kelly green cardigan, a cherry red embroidered coat and an emerald green blouse I just bought and which I had in my car to take back—twice. The rest of my closet is neutrals. I own 21 white shirts and 11 pairs of jeans in standard blue, but those shirts and jeans have style now. My mother, unaware or unable to sit with my shame, teased me when I was young for having a closet that was all neutral: grey, cream, black, brown. The occasional olive green. She still comments if I wear color. I've never bothered to explain it to her.

For me, dressing is an act of defiance. 

I have had to claw my way back to myself and I don't use that word lightly. Healing from complex trauma is a dirty, bloody, ragged-nail, Uma Thurman buried alive in the coffin and scraping at the wood with her bare hands kind of an undertaking.

When I get dressed now, it is me telling the world I survived. It is me calling out that I am allowed to take up space. Right here. Over there. In all the places. 

Farrah Storr, who also writes here on Substack, is a former fashion editor and she just wrote a piece on cleaning out her wardrobe. This subject is everywhere in January, but her article is different. First of all, it's entitled, "How I Learned to Dress Myself aged 45 and a Quarter."

She talks about clothes as holding emotions and sorting your closet by how your clothes make you feel (and we're not just talking joy here) when you look at them: 

"Anger: I have a pair of beautiful jeans in my cupboards that make me furious every time I see them. 

Confusion: If any item of clothing makes you feel this way, it has to go. I have a pair of ketchup-red trousers that confuse me. I have no idea how they even entered my life. 

Wistful: A sunshine-yellow T-shirt that takes me back to a summer in Marseille. A black Eres swimsuit I bought for my honeymoon over a decade ago. 

Safe: Safe things do not turn heads. No one is going to chase you down the train platform to ask where you got a ‘safe’ item of clothing from and yet….I reckon at least 50 percent of our wardrobes should be packed with clothes that make you feel safe."

Clothes that make you feel safe. 

I’ve read that when Steve Jobs was younger, he used to turn up in colorful shirts and bow ties. I wonder if his 100 sweaters made him feel safe as his life became increasingly complex.

I wore a uniform of sorts once, not knowing that I was just trying to feel safe. On most days of my first year at college - I moved away from where I grew up, got my own apartment and started college knowing exactly zero other humans, which was perfect - I wore one of two pair of Levi's, one of a pack of men's oversized white v-neck t shirts, little cropped cowboy boots (those ones that came up just to your ankle, this was 1991) and an itchy, thick, boxy handmade cardigan sweater that would have looked appropriate on my aging statistics teacher. 

This made me feel safe. 

And then one day I bought a red dress. For college graduation. I have pictures. 

I wish I still had the dress. But I do now have an emerald green blouse and a cherry red coat. 

If you want to read more about dressing for oneself, read this.

If you want to read more about learning to belong to ourselves, read this.

If you don't know the Elizabeth Holmes story, watch The Inventor: Out for Blood in Silicon Valley. It's riveting and disturbing. 

If you want to know more about Farrah Storr’s method, read this.

If you want to read more about Anne Kadet’s personal uniform, read this.