Why You Shouldn’t Wear Crazy Socks

Brightly colored socks have become a tech industry mainstay. If you must turn your socks into self-expression, here’s how to do it right.

A by-now infamous 2012 New York Times article argued that, “in Silicon Valley, socks make the entrepreneur.” Hunter Walk, now a seed-stage investor at a firm called Homebrew, compares colorful socks in the tech industry to a “gang symbol.” In the years since, colorful socks have become a kind of plague creeping up the ankles of otherwise well-dressed men everywhere.


We’re not talking about argyle or stripes. Instead, it’s an unholy combination of both, plus multi-colored polka dots and checkerboard patterns in hues that don’t occur in nature. I wouldn’t be surprised to see a marijuana entrepreneur decked out in these weed-leaf foot-bags, available in every color scheme imaginable, including a pleasant white-on-gray. If colorful socks were once an indicator of status, something that only an innovative workplace would let employees get away with, they’re now just a used-up fashion meme that won’t quite die out.

Why did colorful socks suddenly become a Thing? It probably has something to do with the evolution of office culture in general. Mark Zuckerberg’s hoodie heralded a changing world of workwear in which suits, ties, and oxford shoes became not just irrelevant, but symbols of an old, unchanging regime. These menswear outfits epitomized everything Silicon Valley wanted to disrupt—slow bureaucracy, hierarchy, and inefficiency. Move fast and break things! Especially when it comes to stylish outfits.


Colorful socks were perhaps once a way for men’s fashion to catch up with women’s, allowing for a small flash of color in an otherwise dull landscape of browns, blacks, and grays. Since the customary formal garb for the rest of the body has changed, maybe we can start toning down the socks a little, too. If charcoal suits are next to extinct, then the goofy socks that once provided an office drone’s primary means of self-expression don’t have anything to contrast against. Wacky colors against an equally sloppy outfit is just a mess head to toe.


The classic menswear rule is to match socks to pants or shoes. But let’s be more intellectually generous. Socks should simply complement the rest of the clothes you’re wearing. In visual art terms, complementary colors are on opposite sides of the color wheel—red and green, orange and blue. In this pairing, socks provide a highlight instead of a stark departure from the rest of you, as if your ankles had gotten dressed on their own. Denim might go well with some dusky sunset colors. Khakis call for a purple or blue.

Once again proving that it’s the only place to get quality basics in the United States, Uniqlo stores come stocked with full walls of sock gradients. Picking a pair is as easy as MS Paint. Burgeoning American menswear brand Kapital has its own series of “Van Gogh” socks that feature combinations of colors from the Impressionist painter. The preppy mainstay Gant makes compelling socks without going over the top.

Another path is to simply forgo thinking about socks altogether and concentrate on other areas of the wardrobe. Menswear innovation, to borrow a Valley buzzword, has moved into accessories like bags, sunglasses, even high-end phone cases. Pocket squares have yet to return to the mainstream, but they provide yet another avenue for shocks of color.

If Soylent is the tech industry’s take on food, then its version of clothing is bound to end up in a similar aesthetic—uncreative, uninspired, uniform. The future is a world of gray hoodies over sagging gray pants disguising athleisure jumpsuits made of flexible Lululemon-branded “luon” fabric, enlivened only by colorful socks and the blaring neon logos of the companies to which you have donated your data.


Given this inexorable pull, no wonder we’ve turned toward the classic colors and textures of Mad Men, the archetypes of a distant pre-Facebook era. It’s time to put a foot down.