You really don’t want to be that guy. You know the one, the guy who wears the skinny, wraparound sunglasses because he thinks they make him look cool. Because they don’t. What they do is make him look like a photocopy repair man who’s off to Vegas for a long weekend. And we are talking about the wrong end of Vegas here. You know, the guy who’s going to queue to get into one of those clubs which looks exclusive but actually is anything but, where he can drink cheap Margaritas, watch cage fighting on TV, meet new friends, and feel pretty damn ace. Now, I obviously realize that this person is not you—is it any of us?—and I realize that the mere thought of this might make your stomach churn a little bit . . . but trust me, if you wear those glasses, that’s exactly what people are going to think. Even if you’re wearing a big, expensive watch. Because if your big, expensive watch is real, then why on earth are you wearing skinny sunglasses?

The vogue right now is for oversized sunglasses, in the same way that the vogue right now is for oversized spectacles (especially those made by Cutler and Gross). Wearing oversized sunglasses will automatically make you look like Robert Redford or Paul Newman circa 1972, or maybe even Tom Ford circa 2002. Or even Tom Ford right now, come to that. At a push, they might even make you look a little like Alain Delon or Michael Caine in the ’80s, just when they were meant to be on the fade but were actually gearing up for another bout of being ridiculously fashionable. Basically, men are now wearing the type of sunglasses women have been wearing for years—great big oval shades which cover their face as well as their motives. Because the less of you someone can see, then the more enigmatic you become.

Which is certainly not the case with their skinnier cousins.

Skinny, wraparound sunglasses came into fashion in the mid ’60s, largely because of the Velvet Underground, who wore them a) to fit in with everyone else in Andy Warhol’s Factory, and b) because they were “girl watchers.” No, I don’t think Mo Tucker, their very female drummer, wore them for this reason, but the rest of the band certainly did. On the Velvet Underground they looked cool. They also looked cool on British Mods around the same time, as well as literally anyone visiting Saint-Tropez. Back then, you could look like the back of a 1997 Ford Taurus but still look OK if you wore skinny opaque shades. Back in the ’60s, if you wore skinny shades, people might think you were a pop star, a nightclub entrepreneur, a theatrical impresario, or maybe an incredibly hip journalist, you know, one of those who you wouldn’t mind sidling up to you in a bar and interviewing you for a men’s magazine.

Every manager of a pop star in the ’60s wore wraparound shades because their clients did. So if you did too, well, surely some of their magic might rub off. They sent such strong signals: They told both prospective buds and potential girlfriends that you were your own man, that you drove a fancy convertible, could ski and ride, and quite possibly had a private income. Skinny shades said: “Not only do I think I look cool, but I actually am cool, and you’d be a much cooler person if you thought so, too.” Capiche? (“Capiche” being exactly the kind of thing a cool guy who was actually cool would say back in the day.)

Skinny sunglasses disappeared in the early ’70s, as Foster Grants, cowboy boots, and double denim came rushing in (on a horse, obviously) and men started nodding their heads in unison to the Eagles and Fleetwood Mac. If skinny shades had told people how young and hip you were, by the ’70s we all wanted to look older than we actually were. So we tried to look like rock stars as opposed to pop stars, we grew mustaches and started wearing the kind of sunglasses that said in no uncertain terms: I am a dude.

Then, when punk arrived in the late ’70s, men started going wraparound again, trying to look like Johnny Rotten or Jello Biafra. Being cool meant looking like the guys in Devo or the B-52s, and they all wore wraparound specs because they were retro and futuristic and cool and kitsch and ironic and arch and everything else that was going on at the time. In the late ’70s and early ’80s, wearing skinny wraparound sunglasses told everyone you read smart, edgy magazines, watched MTV, and knew someone who worked in advertising. Wearing wraparound sunglasses made you look like an East Coast hipster, someone who not only knew where Downtown was, but who actually went there. Possibly only on Saturday afternoons, but hey, you were cool, right?

Well, not anymore, pal. Because those shades are making you look like a loser. Let me guess what else you’re wearing. You’ll no doubt be sporting a Hawaiian shirt; not an original, or something you found in a Palm Beach thrift store (quite cool), but something you bought instead from a gas station. “Look what I picked up!” you said to your wife, as you proudly walked into the house, as she quickly averted her eyes. And you’ll be wearing a pair of chinos; it doesn’t matter how expensive they were, or indeed where you bought them from, they’re still chinos. And chinos still shout THE GAP 1995!!!!! Of course, you might have redeemed yourself by sporting a pair of Gucci loafers (let’s face it, you can wear anything with a pair of Gucci loafers and get away with it), but if you’re not then you really need to have a word with yourself.

Because, gentleman, you really don’t want to be that guy.

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  Dylan Jones

  Chief Content Officer

  Dylan Jones is Robb Report's chief content officer. A globally recognized figure in publishing with an unparalleled track record of success, he had an extraordinary 21-year tenure as editor-in-chief…

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