It’s funny that both the coolest, best-dressed people in history and some of the least fashion-conscious share a penchant for wearing the same thing over and over again. Consider fashion designer Dapper Dan’s three-piece suits and the cult New York writer Fran Lebowitz’s Anderson & Sheppard blazers and boots, against the identical nondescript T-shirts worn 24/7 by mega-rich tech types.

 What separates them, of course, is intention and flair. For the Silicon Valley billionaire crowd, repeating the same outfit ad nauseam is a productivity hack, albeit one that manages to suck all the pleasure out of getting dressed (and having money, for that matter). On the other hand, for those who understand the power of clothes, a signature look can be a means of affirming one’s identity, melding into and enhancing their personality—the late Vogue journalist André Leon Talley’s appropriately regal capes being just one example of many.

 To some, the prospect of a go-to look might seem dull, much like it would be to eat the same thing every day. But while a head-to-toe rinse-and-repeat look is tricky to execute without becoming a cartoonish parody of oneself—or someone who doesn’t know how to dress for the social context—the best signature looks allow a degree of play. This could be a silhouette—in the case of Talley, his voluminous capes became a canvas for custom creations by the great designers. Accessories, too, offer a way of asserting one’s style without stifling expression in other areas. Jackie O.’s oversized sunglasses not only acted as a shield from the paparazzi but also heightened her mystique, and she wore them with everything from shift dresses to sandals. Prolific hat wearers such as David Hockney and André 3000 also come to mind.

In an era in which we’re flooded with choice, and each passing week brings with it a new “aesthetic” or “core,” there’s something quietly rebellious about embracing a signature look—communicating, as it does, an increasingly rare self-awareness and conviction in one’s taste. And if you’ve learned what works for you and makes you feel most confident, then congratulations: You’ve stumbled upon the secret of dressing well.