A few years ago, the New York Times observed that resolutely unstyled Silicon Valley entrepreneurs and their acolytes were indulging in fancy novelty socks. These mildly transgressive flashes of bright color and bold pattern appeared to suggest a bat-squeak of sartorial awareness among the be-hoodied without compromising their geek-cred with the slightest whiff of fashion victimhood. While some of these men could indeed purchase Savile Row outright, their garish hose were tokens not of oligarchical bombast, but rather of hip whimsy. Enabled by a proliferation of savvy online retailers and sock-of-the-month clubs (certain of which remove the hassle of actual selection), it was a perfect storm of a mass trend. Like the contemporaneously ascendant pocket square, a good pair of eye-catching socks could easily and inexpensively add a dash of derring-do to one’s otherwise drab attire. Steez for straight dudes in straightened times, if you please.

Fair enough. As streetwear, I have no problem with hose as Hot or Happy as they wanna be. Nor should they be necessarily excluded from more classical wardrobes. I have a few myself. But some discretion is called for here. Not for pretension alone do dressers refer to their outfits as "ensembles"; whatever one’s specific tones, harmony is the key, and “popped” notes should generally be shunned as the showboats they are. It was once understood that socks, like ties, should be team players, contributing to an overall effect without drawing particular attention to themselves. Indeed, given widespread prognostication that bold socks are the new power ties, the rise and fall of brash neckwear provides a useful cautionary tale:

As tailored clothing lost ground during the twentieth century to the rising tide of blue jeans and casual sportswear, it shed its more playful elements (e.g. the rough textures, rich colors, and bold patterns so beloved by Apparel Arts connoisseurs) and circled its wagons around the market bastion of business wear. Such bland worsteds allowed little personal flair, with the shiny exception of neckties, increasingly extolled as discrete canvasses upon which white-collared men were encouraged to Go Crazy and Express Themselves. Thus the Jerry Garcia Collection, hand-painted with the crushed hopes of a fallen generation, surely among the many makes of “wearable art” condemned by Tom Wolf as “Pizza Grenade neckties.” Thus also the unfortunate rise of the novelty tie, which, even in the rarefied incarnations embodied by lawyerly Hermès, tended to begin and end the sartorial conversation at: “You like golf? Me too!” (Or perhaps more to the point and desired effect: “I like golf. F*ck you.” Whimsical little icons, after all, whether printed on slick silk or embroidered on salty cotton, generally tend to be totems of wealth or class; when the aesthetic is power, the effect is not elegance, but attitude.)

Tailored clothing and its accessories are increasingly rare and recreational -- less a uniform to callowly subvert than a pleasure to be maturely enjoyed, a pastime to be mastered. Whatever resurgence in popularity neckwear has recently enjoyed owes much to a renewed appreciation for classic patterns and simple solids as elements of elegance rather than expressions of personality. Similarly, socks should serve the whole. This doesn’t require that they be boring. On the contrary, although matching solid hose to one’s trousers is perfectly acceptable, doing so misses an opportunity to play with patterns and colors all the more effective for being unexpected. Think of socks as the knitwear they are, and look for the same qualities you would in sweaters: complementary colorways, pleasing patterns, and quality construction. By all means avail yourself of the more singularly bold options available if they work with the rest of your wardrobe, but leave the Mona Lisa socks on the shelf. A good dresser doesn’t aspire to wear art so much as to wear clothes artfully.

[Originally published in A Suitable Wardrobe.]