The Pajamification of San Francisco

It must have started with the Covid lockdown, yes? The Pajamification of San Francisco?

After all, we were one of the first cities to go full lockdown and log in online. After years of squeezing into skinny jeans and sitting in meetings all day, suddenly, my legs were—quite simply—free. I could lounge in yoga pants all day at home. Yippee hooray! My legs could finally breathe. (Is this how men have always felt…?)

I joke, but you get the point. We went remote, bought loungewear, wore loungewear, then bought more loungewear. Now, we all own matching grey Vuori sweatsuits.

But recently, something jolted me out of my stretchy-pants stupor.

I was at the dog park, and ran into a guy I had chatted with a few weeks earlier. He was sharply dressed: a crisp button-down, slacks, belt, and polished shoes.

“Wow!” I said. “You look dressed up!”
“I just led my first meeting,” he explained.

We’d previously shared a deep conversation while my dog enthusiastically humped his. He had recently joined AA. He explained that AA leaders traditionally wear suits and ties, emulating the founders of the organization.

“My mentor said if I could find a photo of Bill W. and Dr. Bob wearing sweats, then sure—I could too. So, I put on a shirt.”

"I put on a shirt." I loved that line. And looking down at my legging-clad legs, I felt a bit shlumpy.

At this same dog park, men routinely stroll around in pajamas—large, baggy, flannel pants adorned with cartoon characters or rubber duckies. And I have to say, there is something unappealing to me about a grown man dressed like a child. Even the sexiest man somehow loses appeal in kids’ sleepwear. It’s just… not mature.

And women, well, women tend to appreciate maturity.

Single men in San Francisco often complain that the women here aren’t particularly attractive; women say the same of the men. But is it true? Or is it simply that everybody’s sporting sweatpants?

What is this obsession with comfort? Is it really the weather? Do women in Moscow or Tokyo endlessly wear stretchy pants because it’s cold? I doubt it.

Growing up, I remember San Francisco bursting with fashion -- neon colors and tie dye, leather getups in the Castro, flowing skirts in the Haight, bright jackets and scarves in Pacific Heights. Every Saturday, I would explore the city with my sister and Dad -- taking in each neighborhood’s food and distinct look, personality and style. Back then, fashion gave San Francisco a sense of vibrancy and pride. It felt as if everybody was dressing themselves to contribute to this large kaleidoscope mural - the ultimate embodiment of an international, forward-thinking melting pot, filled with diversity, creativity, and fun.

Fashion and glamour are not just superficial or vestiges of a hierarchical, class-driven society. Style is a form of art - a way for people to express themselves, their creativity, their personality, their spirit…

When everybody dresses similarly… what does that say about a culture? What does it say about how they embrace personal expression?

Imagine Paris, Milan, or Tokyo; their vibrant and stylish streetscapes draw millions of visitors each year, fueling thriving economies. When people dress with intention, they communicate pride, confidence, and optimism—not just in themselves, but in their community.

San Francisco’s fashion culture once announced to the world: We are innovative, creative, proud, alive.

Now, the endless muted lounge wear quietly signals the opposite: resignation, isolation, renunciation. Parts of the city are beginning to resemble a giant airport lounge -- and, unfortunately, flights aren't exactly pouring in. Tourism is down ~11% from its 2019 peak, (for a sense of scope, the tourism industry supports ~63,000 jobs.)

Recently, Saks closed downtown. So did Bloomingdale's, Macy’s, and countless other shopping destinations. Sometimes when I ask San Franciscans where they shop, they say “There are no good stores in San Francisco! I do all my shopping online."

Is this really true? Or is it just easier to click “order”? What is the end game of this approach? If we all shop virtually -- what happens to the stores? What happens to the tax revenue they would have collected?

If these trends continue, more and more retail locations will close. There are ramifications for this… Shopping draws tourists - tourists spend money in hotels and restaurants… All of these businesses fuel the economy, and the city is facing a $1 billion deficit.

And so, here is my appeal: For San Franciscans who want the city to be as beautiful, lively and economically vibrant as it can be - maybe skip the sweatpants once in a while. Better yet, visit a local boutique. Pick out something that makes you feel stylish. Wear it out downtown…

It's time to dress like San Francisco is staging a comeback.

Because we are.