wearing: large gold hoop earrings / Chanel lipstick / green western style shirt / dark rinse girlfriend jeans / black leather watch / Chanel fall nail polish / Givenchy handbag / fall suede booties

Last week I attended a How to Macrame class in San Francisco. Dawn from Fashion Should Be Fun and I carpooled up to the city together and snapped these photos of our outfits before heading into the class. I knew the event would be filled with San Francisco bloggers, so I wanted to make sure I was wearing the latest and greatest.

If you had asked me twenty years ago how to dress in San Francisco, I would have told you that San Francisco street style is on the dressy side-no jeans, no sweats, no leggings. If you ask me today what San Francisco street style looks like, I will tell you it is uber casual. Ninety percent of the people walking around in the city are wearing jeans, leggings, and casual ensembles. How and why did this change in style happen?

There are a lot of factors which have contributed over the years to the change in San Francisco street style. My Mom will tell you that people wore their very best to go downtown in the 1950s and 1960s. Women wore heels, gloves, and hats. Men would wear suits and scuff-free loafers. People used to take pride in how they dressed; especially when heading to downtown San Francisco.

The 1970s were still dressed up; but the overall style in the 70’s was more casual with the advent of sport coats for men, and pant suits for women. The wrap dress was also popular; and it gave off a more casual vibe then popular dresses from previous decades.

In the 1980s and 1990s, companies in downtown San Francisco still required men and women to wear suits to work. When people came into the city from the suburbs, they still dressed up and adhered to the no-denim, no casual clothing fashion rule. It was at the dawn of the new millennium when everything changed; and it changed fast.

The dot-boom brought in new start up companies to the Bay Area, and in San Francisco proper. These tech and internet companies were run by many GenX-ers and Baby Boomers who wanted to create something new; and not work for “the man” like their parents did.

Our start-up culture in San Francisco was focused on work, work, and work. These new companies did not have a dress code; allowing workers to wear casual clothing, jeans, and show off piercings, colorful hairdo’s; and essentially express themselves through their clothing.

My job moved from the East Bay to downtown San Francisco in 1998. I wore a suit to work everyday. If I wore a pantsuit with a shirt that did not have a collar, I was told my clothing was too casual. No joke. Then, in 2000, something changed. The start-up culture took over San Francisco street style, and changed the way we dressed for work; as well as heading downtown for dinner, shopping, and in general.

All of a sudden, start-up culture took over, and only the finance, insurance, and consulting workers were still walking down the street wearing suits. Montgomery street, which used to be a sea of suits, suddenly became a sea of jeans. People were not just wearing jeans, they were wearing old sneakers, ratty backpacks, and old sweatshirts. And no, they were not homeless; these were highly paid workers from the new tech and Internet start-ups which had popped up South of Market and downtown. These workers changed the fashion of the city. Suits were no longer “chic” or “cool.” They were stuffy, old school, and considered something from our parents generation.

Since it was the dot-boom, I left my conservative, old school job on Montgomery street and joined a start-up in 2000. I cannot tell you how difficult it was for me to switch to wearing jeans at work. I felt grubby. I felt. . . under-dressed and inappropriate. Jeans were always something I loved on the weekends, or when I was not anywhere near downtown. They were something I would never wear if I went downtown to shop or eat out. Jeans were off-duty clothing; they were casual. To wear jeans downtown felt wrong; almost obscene.

I did the dot-com thing, and the wearing jeans downtown thing, for a little over one year until the dot-com I worked for was about to dot-bomb; then I went back to an old school company down the Peninsula and went back to a no-denim dress code. It felt better; I have to admit!

The street style in San Francisco never reverted back to what it once was. The streets of San Francisco remained casual, and continued to grow more casual as time went on in the new millennium. I still question myself when I choose to wear a denim outfit in San Francisco, but when I arrive in the city, I blend in.

I lived in San Francisco for ten years. In those ten years, I watched San Francisco street style go from refined and dressy, to casual and sometimes sloppy. When I was growing up, San Francisco was the center of fashion for the Bay Area. As an adult, I feel like the suburbs dress up more then the city. It is a strange turn of events. It will be interesting to see if a new industry pops up soon, changing the city style landscape back to dressier times; or if the casual culture of the tech industry dominates for generations to come.

Shop my casual San Francisco street style look:

What are your thoughts on San Francisco street style throughout the years? What have you observed?

Thanks for stopping by!

XOXO

Cathy