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Dressing the Part: Why I’ll Never Look My Best in This Town

For years—13 of them, to be exact—I’ve been trying to become a San Franciscan. Or really I should say, for 13 years I have been trying to look like a San Franciscan. Every season or two, I think I make some headway—a streamlined brow, boyfriend jeans, a perfect pair of wedge-heeled boots. But I never quite pull it off, and at long last I think I understand why.

The knowledge that I was yet again failing to convince anybody about the true coordinates of my native habitat came to me most recently in New York City. It never comes here, at home. It always comes on the East Coast, where I’m from, and it always comes from Dan, my wave-riding, rock-climbing California-born-and-raised husband. This time we were walking through Central Park. We’d flown to New York to visit my brother, who doesn’t just look like a New Yorker but also insists he couldn’t be funny west of Newark (and I’m not sure he’s wrong). I was wearing pretty much the same clothes I wear around Bernal Heights—jeans, flats, a “good” T-shirt—a fact that I know will upset my most fashionable San Francisco friends who reserve whole sections of their closets for “New York only” apparel: knit rabbit scarves, Louboutins, stuff you just can’t possibly wear here unless you want to look like a hooker, a rabbit killer or worse. (For a while my friend Amy did try to wear her knit rabbit scarf in San Francisco, always taking the time to explain to anyone who would listen that the bunnies were shaved in the most humane way and given little sweaters to wear so they didn’t get cold. But still she felt like a rabbit killer.)

Anyway, that day in Central Park was beautiful: sun shining, snow melting, 50 degrees. We passed Sheep’s Meadow and spent a small fortune on hot dogs, trying to stem the hunger of our endlessly famished 7-year-old daughter who is growing faster than kudzu. Everything felt deeply right. We met old friends under the cuckoo clock at the zoo. Then Dan said that thing he always says when we go to visit my brother, that thing that I find so confusing because we live in San Francisco, I love San Francisco, and we don’t intend to move: “Honey, you always look so great in New York.”

I’ve developed a theory: We all have a city in which we look best, a city that somehow aligns with our values and brings out our best selves, that same way certain blue-eyed redheads look great in teal. My friend Kiernan—raised in New York, living in Glen Park—looks best in Seattle. Something about her compact, spring-loaded body and the pure twinkle in her eyes. My friend Sunny looks best in Chicago. She has the strong shoulders, which she pairs with tattoos and leather pants. Everybody’s always falling in love with Sunny in Chicago. Hell, when I lived in Chicago, my boyfriend, who’d fallen in love with me in New York, went to walk our dog and fell in love with Sunny. Now they’re married. She’s irresistible there—fabulously, unflaggingly cowpunk.

So who looks best in San Francisco? If I do say so myself: Dan. He’s outdoorsy, casual, opposed to conventional displays of wealth, equally comfortable surfing Ocean Beach and making pickled radishes from Thomas Keller’s latest cookbook. He usually wears the male SF standards: Patagonia, graphic tees, loose weathered jeans. Occasionally, however, Dan pushes it too far. For a while last summer he traded his Vans for those horrid five-finger shoes that look like gorilla feet. One afternoon, at a friend’s garden party, I found myself explaining that “we’d” had the gorilla shoes for five months—“we” not “he,” as if “we” were pregnant. But now Dan’s back in his Vans and he looks great. In New York he looks like a noble savage. I think he likes it that way.

Who else looks great in San Francisco? Anne—always in long necklaces and layers, quirky without being trendy, fully and only herself. Nikki, too, unfailingly gorgeous and calm, in her gorgeous and calm knits and jeans. What’s the secret? I don’t know entirely, but here’s a start: mixed, loose clothes, like our mixed, loose weather. Dressing privately, or appearing to do so (with fashion it’s always hard to tell what’s truly private and what’s a private look). Tailored clothes are hard to pull off—they look too aggressively status-hungry, too much like sartorial armor. You have to look like you’re dressing for yourself, like you dress like this at home. You can’t appear to be trying too hard. You have to seem swept up in the great experience of your great, original life.

Part of the problem for me, I think, is a look I have in my eyes. Within weeks of moving to San Francisco people started describing me as “real.” I didn’t know what they were talking about at first. For a while I thought it was my un-highlighted brown hair. By now I realize the problem was, and is, much deeper. I have an innate literalness, a lack of cool, a feeling that if you casually discuss with an acquaintance getting together for coffee sometime, you should follow up the next day to set a date.

I’ve learned not to do this, most of the time, but I still look like I want to, and that raw apparent hunger, that obvious craving, is not very San Francisco. It’s New York. I think even if I adopted Anne’s wardrobe, or Nikki’s, I’d still look too ambitious here and utterly at home in Central Park.

But I have very high hopes for my daughters’ styles and their relationships to this city. The older one, who looks like Dan, is a San Francisco natural. She gives off the aura of a gorgeous little wahini, a mini “lifestyle pro,” one of those surfers paid not to compete but just to look great in surf trunks. The younger one does have my eyes, a liability in this state. Yet at age 4 she’s already altering her clothes, cutting off her leggings into biker shorts. She has a precocious and indefatigable interest in body art. She’ll have Mission funk wired by the time she’s 10. I suspect she’ll go live in New York, but at least when she comes back to visit, she’ll feel like she’s returned home.