The real crime in San Francisco: Fashion
Suits with backpacks, ugly shoes, and skinny jeans. Derek Guy spills the tea on everything we get wrong.
By Derek Guy
In San Francisco, there is a fresh crime wave that no DA can stop. Emboldened criminals are rushing around the streets wearing backpacks with suits, tan shoes with dark worsted slacks, and Patagonia fleece vests with chinos, dress shirts, and Allbird sneakers. Let's take a look at some of the city's most common fashion offenses today, as well as potential solutions.
Bad Sneakers
I say this with great affection: many San Franciscans should be required to obtain a permit before purchasing a pair of sneakers. Allbirds, On Clouds, and anything that can be described as a "dress sneaker" have the feel of $15 ham-and-cheese sandwiches in triangular plastic containers. They're business conference rooms with floor-to-ceiling windows, and the Zoom conference calls could have been an email. These companies don’t do casualwear very well, nor do they have the professionalism of dress shoes. They sit awkwardly between two worlds.
Solution: You can’t go wrong with the classics: Nike Jordan 1, Air Force 1, or Air Maxes; Adidas Sambas or Stan Smiths; Converse Chuck Taylor 70s or Jack Purcells; New Balance 574s or 1400s; and Vans Authentics, Eras, or Old Skools. If those strike you as too boring, check out Nike’s Tailwind 79s or Waffle Racers; Adidas Country OGs; New Balance 550s; Spalwart Marathon Lows; Novesta Marathon Trails; Shoes Like Pottery; German Army Trainers; and Doek Oxford Canvas. These sneakers are much more firmly planted on the casual side of things, and as such, don’t masquerade as something they’re not. If you need something slightly dressier, buy a pair of penny loafers or chukkas from Meermin, Carmina, or Alden.
Business Causal
The Bay Area is known for its business casual attire. After all, we invented jeans, and Docker's—under Levi's leadership—helped bring in the Casual Friday movement in the 1990s by sending out brochures to human resources departments to advertise their chinos. Because of the emergence of Silicon Valley, the hoodie and jeans uniform became the symbol of meritocracy and The New Economy, replacing the coat-and-tie style of established industries in the East.
This transition, however, has not completely freed males from the respectability of dress attire. As a result, rather than wearing whatever they want to work, many people struggle through the day in a dress shirt and chinos, accompanied by a black nylon business bag or, worse, a backpack. This uniform lacks the attractive qualities of conventional tailoring as well as the creative expression of good casualwear. It’s basically the suit without the tie and jacket, leaving men with the worst parts of the uniform.
Solution: Most guys would be better off simply moving up or down the formality scale. If you work in a business casual environment and must wear a dress shirt and chinos, at the very least put on a sport coat (try Suitsupply at 175 Maiden Lane or Spier & Mackay online for something more affordable). If a sport coat is too formal, go for raw denim jeans from San Francisco's Self Edge, then head to Taylor Stitch for flannel shirts and the Alden store for unlined chukka boots or loafers. If you need a jacket, check out Uniqlo, J. Crew, Todd Snyder, Wasteland, or Standard & Strange in the East Bay.
Overly Tight Clothes
The history of fashion is often written as a series of irrational swings and turns with no agency allowed for the participants. Women’s hemlines rise and fall; men’s suits get baggier or slimmer. But there’s a better way to dress. Instead of following whatever editors and designers dictate, you can think of clothing as cultural language and dress for your body type.
There are ways to wear slim—sometimes even skinny—clothes well. Skin tight jeans wrapped tightly around one’s thighs and calves look great when paired with black boots because of our collective memory of rebel rockers such as the Sex Pistols. But nowadays, men in San Francisco are wearing slim business casual clothes that bear no resemblance to those rebellious times. Instead, the styles just sit downstream of early 2000s trends and often do little to flatter the wearer’s figure. Short suit jackets flare out around the hips, making the wearer look heavy. Dress shirts are tailored so tightly around the body, the sleeves look like sausage casings. Flat front chinos are cut so tight, they have to be made from a cotton-stretch blend, otherwise the wearer would have to walk like the monster of Frankenstein.
Solution: A good outfit should flatter your body, not necessarily recreate its lines. Be honest about whether your clothes are too tight. If you see your trouser’s hip pockets flaring out like a charging elephant’s ears, that means the hips are too tight. If the legs catch on the back of your calves when you walk, the legs are too slim. Jackets and shirts should be built for comfortable movement so that you can hug someone without feeling like the back seams are about to split. If you need custom office clothes, visit Tailor’s Keep at 618 Washington. They’re the best custom clothier in the city.
Dark Suit Without a Tie
To the degree that men in San Francisco still wear a suit, many will ditch the tie in a half-hearted attempt to make it look casual. But a dark worsted suit worn without a tie is like the night sky without stars. Without the decorative element that a tie typically brings, the shirt ends up looking too empty between the coat’s front edges. The wearer thinks they look like George Clooney, but they always end up looking like the type of guy who despises having to wear a suit to work.
Instead of simply removing the tie, make the outfit appear more deliberate. You can avoid wearing a tie by wearing knitwear instead of a dress shirt—a thin crewneck merino sweater, a long-sleeve polo, or, if the weather permits, a turtleneck. The tie was never meant to be there in the first place, and the slight texture of the knitwear fills in the space where a necktie would normally be. Alternatively, you can also just wear a more casual suit—tan cotton suits, tobacco linen suits, or even grey Thornproof tweeds. Although not appropriate for the office, a casual suit without a tie is ideal for dinner parties, dating nights, or an evening at the San Francisco Opera House.
Suit Jacket with Jeans
If you're going to a formal function, don't just wear a suit jacket with jeans. The result is usually that you look like you spilled something on your suit pants and had to change out of them. The formality of the suit jacket—often made of a dark worsted wool in a color like navy, or even worse, grey—combined with the casualness of the jeans—often too slim and low rise for the coat—looks like a sartorial mullet.
While certain types of suit jackets can be worn with jeans, purchasing sport coats is a simpler approach. These are usually made of somewhat rougher materials or have bolder designs that set them apart from the silky, elegant suit jackets that require matching pants. Sport coats are more informal and, as long as you obtain the proper kind, may be worn with denim. Purchase a pair of dark Levis Vintage Clothing 1947 501s at the Levi's store at 815 Market Street. This way, you bridge the gap between the formality of the sport coat and the casual nature of the pants.
Derek Guy is a fashion industry writer and commentator. Follow his musings on Twitter/X and Die, Workwear!
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