How to be an S.F. hipster

You know you aren’t hip when you stand out like a sore thumb in the Mission. Recently, my husband and I were there, and we were awestruck by the utter hipness that has overtaken Valencia Street. Were we asleep the last five years? It was date night, so we couldn’t have possibly looked less cool or more out of place. Let’s just say that if someone were playing Where’s Waldo? and we were Waldo, the game wouldn’t have lasted a minute.

I have never considered myself a hipster. There were times when I considered myself cool, but cool did not require doing very much. Being laid back was cool. Not caring too much was cool. For example, I didn’t care at all when, many years ago, I wore a pink pastel jacket in New York after Labor Day. Wait: That turned out to be uncool. I walked into a designer’s clothing store on Madison Avenue and after surveying all of the über-chic clothing, one of the employees turned to me and said, “Are you from L.A.?” Two salespeople tittered softly. For a moment, I was thrilled that they took an interest in me, but just as quickly, I realized it wasn’t a compliment. It was my jacket. Ugh. But other than that one humiliating New York moment, I think I have been fairly capable, post-Aptos Junior High, of holding my own in fashionable circles — though never to the extent of a hipster.

Being a San Francisco hipster requires much more effort than simply being cool. You must be intelligent (just look at them!) and sadly, that’s not something you can go out and purchase like an accessory, or say, a pastel jacket. Google Glass may be of some help in the near future, but as of this moment, you have to be intelligent on your own. Hipster friends have explained to me that hipsters only look smart — for example, attending all of those pop-up store and art gallery openings and of-the-moment lectures, like “27 Ways to Cook Sustainable Placenta,” all the while lugging tattered notebooks in their arms with who-knows-what-brilliance written inside.

Serious glasses — those big faux tortoise-shell frames that only very famous directors or Elvis Costello can pull off — also accentuate the hip look. I mean it’s no easy task to look good in those clunky things. Of course, before buying a pair, there is that prerequisite of subpar vision, which means you have to read a lot. This will take time, so be patient. In the near future, you could be one of the lucky ones who can’t see worth a darn.

Then there is the Messenger Bag. I tried to buy one several times, but I couldn’t find anything that looked remotely as amazing as those worn by the hipsters. Theirs have a worn-out patina with a “just-back-from-a-1,000-mile-hike-in-Belize” look. The only ones I have found either hang barely below my armpit, were made of hard plastic, or had a pink Hello Kitty plastered on the flap. Still, messenger bags must be inexpensive, because hipsters are not rich — I mean, they’re kind of grubby-looking in their too-tight-Wes Anderson-by-way-of-Goodwill camel hair sweaters. A hipster friend explained that I have been duped by the hipness of it all. Hipsters are not poor. They are actually more often than not very well employed, middle to upper-middle class kids working at dot coms and financial institutions in San Francisco. Wow, that was a revelation. Now I know how they can afford all of those restaurants on Valencia!

While my husband and I stood awaiting the arrival of our friends at one of those aforementioned restaurants, we were hypnotized by the parade of sophisticated, artsy-looking young people passing us by. It was a sea of women in flirty, pale, chiffon skirts with very thick black tights and hiking boots and for the guys, tattered vintage shirts and below the knee khaki shorts (it was a warm night), each sporting the essential Messenger Bag.

I turned to my husband and asked if my outfit of boots, leggings, and a long, asymmetrical cardigan looked, well, kind of hipster-ish? Without a pause, he answered, “No, but you look really nice!”

I quickly slapped on my reading glasses and looked up at him again, tentatively. My husband just shook his head gently, thinking his slow movements might lessen my disappointment.

“That’s OK,” I said, “I’ll settle for comfortable.”

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Sandy Fertman Ryan has written for numerous national magazines, including Parade, Seventeen and TEEN. Her hobbies include folding contour sheets and watching water boil. E-mail: [email protected]