I grew up in a rural, small town on the central coast of California, far from big city trends, and long before the Internet made even the most obscure subculture fashion instantly and globally accessible. In high school I experimented with fashion pieces compiled from thrift store items and my father’s discarded garments of yesteryear; this was my half-baked conception of punk. My look included boots, ill-fitting blazers, cardigans, buttoned-up shirts, and ties.

In my early 20s in Santa Cruz, came my anti-fashion phase. I bought five identical outfits: white wifebeater, white T-shirt, khaki pants, and the ugliest Kmart Velcro shoes I could find. I looked the same every day, like a cartoon character. I was delighted – women were not. Like ZZ Top says, “Every girl’s crazy ’bout a sharp dressed man.”

Within the last few years, I’ve reevaluated my situation and decided to add some pizzazz back to my look. Even so, my friends here in fashion-conscious San Francisco describe my style as “creepy Mr. Rogers” or “if Cliff Huxtable were a bro.” Apparently, my look is an acquired taste. While I’m totally comfortable and happy with my look, I thought it would be fun to walk in another dude’s shoes. I decided to let three local clothing shops outfit me in their visions of San Francisco style.


Cable Car Clothiers is a San Francisco institution. An American interpretation of an old-world clothier and haberdashery, Cable Car has been keeping the well heeled of the Financial District in English wool and Italian silk since 1939. A portrait of Queen Elizabeth II hangs under crossed British and American flags, and the interior is all dark wood and cornices. A glass case by the door is filled with male grooming accouterments, sheep’s fat soap, and aftershave lotions so elegant they make Acqua Di Gio smell like Axe Body Spray.

Entering the showroom, I am greeted by store manager James Crittenden-Cavendish. Actually, his title is much longer than his name – it wouldn't fit on the student ID he shows me from his prestigious British university – and mentioning it here would be, as he puts it, “indiscreet.” Let’s just say his family tree probably includes people whose faces have been on currency. James speaks in paragraphs – the kinds that have semicolons and footnotes. Over the next half hour, James lays out his treatise on men’s fashion, which touches on the influence of formalist philosophy, among other concepts I half remember reading about between bong rips in college. 

A self-described “young fogy,”  James laments that his look is a little less unique these days as more young people are dressing in the styles of their forefathers. He sees it as a movement to reclaim a cultural history. James says that Americans lack an ethos and their need to find a common story shines through in various forms, including fashion. On sagging, for instance, he remarks, “I’ve heard the trend found its inception within the American penal system.” My inner Butt-head thinks, “Uh huh huh huh. He said, ‘penal’.” All this smart-people talk is making my brain hurt. I decide it’s time to get suited up.  

James outfits me in a navy Southwick three-piece suit. The Egyptian cotton shirt he hands me feels like the gossamer wings of a butterfly, and the Spanish gold crocodile cuff links make me feel like a gentleman hunter just back from safari. It is definitely the most money I’ve ever had on my body. If it gives you any idea of where I’m coming from, the last time I bought a suit was eight years ago for my cousin’s wedding from the Men’s Wearhouse. A suit I later returned.  

James hands me a pink bow tie with little blue swordfish on it. “Nautical. Very San Francisco,” he assures me. “I don’t mean to be insulting, but do you know how to tie a bow tie?” he asks, wincing. I glance at the nearby how-to diagrams for tying bow ties and ascots. “Uh, I forgot,” I mumble. James dutifully assists me. “We encourage the wearing of bow ties here,” he informs. 

No look is complete without accessories, so I scan the store for items to complete my look. I try on a couple of hats and pick up a smart wooden-handled umbrella, but I eventually set my sights on the pièce de résistance – a sterling silver cane. “Is there a sword in it?” I ask excitedly. “I’m afraid not,” James frowns.  

As fun as it is to dress up a three-piece suit and twirl a cane, I was a bit out of my league. I thank Mr. Crittenden-Cavendish and head for my next fashion destination.

I journey from the heart of the button-down Financial District to hipster haven Valencia Street. I've been shot down by girls at enough bars in the Mission to realize that maybe it was time I upped my “cool kid” fashion game. Afterlife looked like just the place to do it.  

At Afterlife I meet Danielle, who co-owns the store with her brother, Luke. She is smartly dressed, soft-spoken, and shares some strawberries with me. The shop is modern and stylishly decorated, with an old jukebox and pinball machine added as retro flourishes. Unlike the haphazard bins and racks I'm used to searching through to find my vintage treasures, the layout is clean and well organized.  


Danielle tells me that Afterlife is about mixing old and new. In addition to hand-selected secondhand items, it has a wide selection of new Cheap Monday jeans and accessories, including reconstructed vintage and sterling silver jewelry that Danielle designs. Above the racks of clothing, several T-shirts hang on the wall, almost as decoration. Danielle tells me her brother had been collecting rock concert memorabilia tees over the years. They’re for sale, but are really rare and expensive, and usually only get sold to die-hard collectors.   

I quiz Danielle about men's fashion in San Francisco. She finds San Francisco style similar to that of her native Seattle, but very different from LA, where she does a lot of buying for the store. “What comes to my mind is sort of a more relaxed fit,” she tells me. “Not to say there isn’t a lot of effort ’cuz I think there is, but it’s more natural.” Being in the heart of trendy Valencia Street, I ask her what is hot at her shop right now. She points to an assortment of flamboyant Justin western boots, vintage flannel-lined L.L. Bean jackets, and small-squared plaid shirts, all of which are selling like hotcakes. I ask Danielle to pull together a couple of outfits that would help me fit in the unforgiving, hot-or-not Mission district. 

Danielle dresses me up in a few outfits that make me feel right at home on Valencia Street. Looking in the mirror, I feel compelled to stop shaving, grab a sixer of Pabst, and head for Dolores Park. One weirdly patterned cardigan I try would be right at home in my closet among the collection of “strange uncle” outerwear I have acquired over my years of thrift-store shopping. She pulls down a vintage Rocky Horror Picture Show T-shirt off the wall that is perfectly worn to the point of softness and lightness that only years of washing and TLC can impart. I also try on a pretty rad leather jacket that would have gone home with me, if it weren’t a tad too small. And anyway, I can’t lift my arms to shell out 300 dollars for it. I take one last look at the weird cardigan and consider taking it with me, but I have to travel light to my final destination on my San Francisco style tour.


It’s a short jaunt from Valencia to Sanchez, but I enter into a completely different world of style when I reach Unionmade, a store that harkens back to a traditional American look. The embodiment of the reclamation of cultural history that James at Cable Car described, the store is a mixture of Americana and modern men’s fashion. A collage of bandannas, WWII navy photos, pictures of greyhounds, a cowboy-themed Levi's ad from the ’50s, Coca-Cola bottles, Buddy Lee dolls, and model ships pepper the clothing displays. A section devoted to men’s grooming features a book titled The Bearded Gentleman among the straight razors, shaving brushes, and lotions.

I meet the owner, Todd, just as he’s opening up shop. A former senior creative director of advertising for Old Navy, Todd opened Unionmade nine months ago and is pleased with how well business is doing. Being so close to the Castro, he thought his clientele would primarily be gay men, but the shop’s proximity to the Mission, as well as blog shout-outs, has brought in a surprisingly diverse cross-section of San Franciscans. His overall concept for the store is an “edited assortment of easy-to-wear, high-quality men’s clothing.” Todd envisions Unionmade as an alternative to the Euro-y fashion boutiques that dot the city. He focuses on American heritage and special lines.   

When I ask him to describe San Francisco style, Todd makes the comparison to Brooklyn. “The aesthetics are similar to Williamsburg, but we’re a lot more crunchy, earthy here.” Todd says that the high cost of living prevents people from blowing too much on high fashion. People here are more understated, and although they pepper their wardrobe with thrift-store items, they still demand quality. 

Todd puts me in a red varsity jacket made locally and exclusively for Unionmade by Golden Bear, a tie made from vintage Japanese silk by The Hill-side, and some 1944 Levi’s 501s. I feel comfortable and stylish, but still not quite in touch with James’ elusive “American ethos.” I try on some amazing Alden oxblood saddle shoes – definitely the nicest and most expensive things I’d ever had on my feet. Todd tapes the soles so that I can't scuff them up, but I still won’t go outside with them. Knowing me, I’d end up planting them right in the nearest pile of dog poo. 

As Todd fusses over my outfit, I calmly take it all in. I am starting to get used to the whole dress-up thing. Buttoning up my jacket, he gives me a once-over. “You look good,” he says, satisfied with his handiwork. “I should have been a model,” I joke. “Yeah, we all should have,” he replies with a sarcastic smirk.  

By the end of my fashion tour, I feel like I’ve been through one of those whirlwind dress-up montages in an ’80s movie, where they make over a nerd into a hip, trendy teen. It was fun to dress up in fancy suits, cool vintage duds, and artisan jeans, and I can see myself incorporating some of the ideas and details from all three of the stores into my own signature look. But sorry ladies, I won’t be throwing out my Cosby sweaters and patched-up slacks any time soon. At the end of the day, I gotta be me.

For the peak of Financial District elegance, head to Cable Car Clothiers. Class comes at a cost:  A pair of socks can cost as much as $40 and a three-piece suit will throw you back about $1,500. For a more affordable, vintage look, head down to Afterlife in the Mission, where you can get outfitted in a mix of new and old duds. Many vintage items are in the $20–$30 range, but rare items like the Rocky Horror memorabilia tee are in the triple digits. Seek out some American heritage at Unionmade, including brands like Levis, Taylor Supply, and Mark McNairy. You can get outfitted, from head to toe, for anywhere from $600 to $2,000.