This article is part of SF Throwbacks, a feature series that tells the stories behind historic photos of San Francisco in order to learn more about our city’s past.
Once known for our creative and unique streetwear, lately the Bay Area is more of a sweats-and-pajama-lover’s paradise. We have fully embraced lounge chic, or maybe not so chic. The Bold Italic thought it would be fun to revel in the styles of our city’s past, so we decided to go back exactly a century ago to the roaring ’20s.
San Francisco’s style in the 1920s looked a lot more dapper. But hey, they had just come out of their own 1918 pandemic, so let it inspire you to what 2022 could bring.
Fresh out of a period of death—World War I and the Spanish Flu that killed even more people than the war—the people who had survived were ready to live life to the fullest when the 1920s arrived.
Fresh out of a period of death — World War I and the Spanish Flu that killed even more people than the war —the people who had survived were ready to live life to the fullest when the 1920s arrived.

This photo of the ballroom at the Palace Hotel shows off some of the elegant styles that were popular for evening attire at the time. In this new era, women shed the constricting, high-necked dresses of the past in favor of more fun, loose dresses they could actually move in. Although the Palace burned down in the 1906 earthquake, it was rebuilt quickly and became a destination for San Francisco’s most important visitors, including President William Harding and his wife, Florence.
San Francisco’s 1920s fashion wasn’t confined to stuffy ballrooms. Flappers had a whole look themselves separate from more mainstream society. These women dressed to party, and party they did — with the help of illegal spirits at the city’s many speakeasies, where hard liquor was aplenty. Flappers defied the prohibition, used slag, took lovers, and had a certain look that disregarded established trends. Their dresses were beaded, sleeveless, flashy, form-fitting, with dropped waists and high slits. Designers like Gabrielle “Coco” Chanel helped inspire and create these styles.
People got dressed up just for a regular day out, too — and there was an outfit for everything: sports, travel, daytime, evening, housework, etc. But out and about in the world, people looked put together. These days San Francisco is almost comically casual (sneakers at the opera, anyone?), but in the 1920s the only people who dressed in casual clothing were laborers.
Everyone who could dress up did so to signal upward mobility and status. And since the iconic fashions of the 1920s — like simple dropped-waist dresses in light fabrics — were more economical than high fashion had ever been before, ordinary people could easily dress “on trend.” The styles that came out of the 1920s are often referred to as “the democratization of fashion” since they allowed everybody to dress up.

As mentioned, 1920s clothing styles were also different from the previous Victorian fashions because — game-changer — they allowed people to actually move. As we can see in this photo of women visiting San Francisco from the Chicago Opera Company in 1922, they were able to walk, step, and reach in their dresses without inhibition.

Although the fashions of the ’20s were much more comfortable than what came before them, they were hardly revealing — especially at the beach, and especially for women and girls. Swimsuits still usually covered most of women’s bodies — and if they didn’t, they could be arrested (not a joke — see photo below.)



The ’20s involved changes to children’s fashion, too. In San Francisco and beyond, kids’ fashion in the 1920s was innovative in that it was actually designed for them. Before then, most children were just dressed as miniature adults.
During this decade, as people enjoyed the liberation that came from the end of the First World War, the first true kid’s clothes appeared. That meant comfortable cotton dresses for girls and shorts for boys that were loose enough for them to play in. Most kids also wore hats and knee socks. The children in the photo below are waiting to see the 1920 movie Shipwrecked Among Cannibals at the Frolic Theater on Market, dressed to the nines since movies were considered formal events in the ’20s and ’30s.


The fashion of the 1920s was all about rule-breaking. The little girls in the photo above, taken in San Francisco in 1920,have short hair,loose dresses, and lots of attitude.
The styles of 1920s San Francisco were innovative and effortlessly cool. If we want to live up to our fashion forebears, we might have to upgrade our quarantine wardrobes.
The Bold Italic is a not-for-profit media organization, and we publish first-person perspectives about San Francisco and the Bay Area. We operate under a fiscal sponsorship of a 501(c)(3).
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Happy Pride, again

For the past year, The Bold Italic has been queer owned and operated. (This part you should already know.) It is also now fiscally sustainable at its base; meaning we have enough in ad revenue, subscriptions, and nonprofit grants to pay for its website hosting and software services.
We do not yet have enough to pay any writer full-time, but in late February I feared having to shutter the website entirely. So this is meaningful progress I am very grateful to have. I've worked very hard to build up our infrastructure and metrics, and to monetize them. Ad revenue is consistently coming in from both the website and social media now.

SF fashion through the decades
Here's another story on SF fashion from the 1950s.

I also loved this photo recently spotted on Facebook, taken by Ray Morse. Casual Corner at Geary and Powell in the 1990s.


"And then cerulean quickly showed up in the collections of eight different designers. Then it filtered down through the department stores, and then trickled on down into some tragic Casual Corner where you, no doubt, fished it out of some clearance bin."
Then of course this classic snapshot of SF fashion taken at Hole in the Wall, circa 1999 by Chloe Sherman.

Recently seen at SF fashion shows
The best fashion show in recent memory was the Pride show at Glide Memorial. At first I thought they were all original designs until one model noted he was in a McQueen. (And obviously of the Sarah Burton era.) Glide if you're reading, I felt hypothermic waiting in line outside. Whyyyyy. The after party was likewise a wind tunnel of sadness. But I loved the show.

Ms. London Breed looked especially radiant. I feel bad for her and Joel Engardio and yes I made a political opinion known here thanks.


The one above was one of the simpler silhouettes, and the gloves brought it into costume territory. But I loved it.
No idea what this brown dress is, other than amazing, and I assume has made the rounds on other runways.

This one is getting lots of attention that I'm not going to mine for clickbait today. Suffice to say his runway walk is as awkward as his general charisma. Lol.



Above photos from Drew Altizer Photography, and below there's one from me. No notes needed on the after party ambiance.

'Vogue World' could come to San Francisco
I have so many thoughts on this one. Call me a hater but.

Vogue has been hosting this one-night runway show spliced with a pop-culture variety hour, stacked with musical performances, celebrity guests, and a local cause to benefit. It debuted in New York in 2022 and has since touched down in London, Paris, and Hollywood, with Milan on deck this September. The 2027 edition could land right here.
And my question is: Freaking why?? Yes of course I would love San Francisco to evolve beyond being the denim-and-hoodie capital of the U.S. But we are in fact one of the least fashionable cities in the country. And now we could play host to one of fashion's glossiest nights. It could really be fabulous. I just hate that it's being dressed up as some comeback story, when really it's money. Of course.
At this past Met Gala, OpenAI, Meta, and Snapchat each bought a table at $350,000 a pop. Mark Zuckerberg turned up for the first time and reportedly shared a table with Wintour. Fashion's biggest night pulled in a record $42 million, and Silicon Valley wrote many of those checks.
But also, we've had some signals this sort of event might be coming:







