Lifetime achievement for best mug shot goes to Frank Sinatra.

The FBI agents are at the door, and you don’t really have time to put yourself together. A flash of fashion inspiration is what’s needed, because chances are, these fellows are not going to allow you time for a shower and shave. But with a little luck, you’ll get to duck into the boudoir for some primping, because you’re going to the slammer, and as everybody knows, the most important thing about jail is to leave with a great looking mug shot. Ideally, one that’s good enough to put on an actual coffee mug.

At minimum, nice enough that you won’t be embarrassed to see it on Instagram. Because as Oscar Wilde once said, the only thing worse than people talking about you is people not talking about you. But it’s not so great having them talk about you saying things like, “Did you see that mug shot? It looks like he’s put on weight,” or “That t-shirt looks like it was used to wipe bugs off his windshield!”

David Bowie masters mugshot mystique, in upstate New York, 1972.

There are worse things than being arrested in the USA. Being arrested in North Korea, for one. Or getting barrel-bombed with chlorine by your head of state, for another. Human plague could be sweeping the neighborhood, as is happening now in New Mexico (which we’d think “fake news” if we didn’t read it on NPR).

So chin up! Suit up! Look smart! And everything will be fine.

Men, when it comes to mug shots you really can’t go wrong with a crisp dress shirt and sport jacket.  Ever the iconoclast, Frank Sinatra opted for a tux. Only 23 when he was hauled into the clink by New Jersey police, Sinatra was arrested for having intercourse with “a woman of good repute” who was not his wife. As it turned out, she was someone else’s wife, diminishing her repute and  getting Sinatra’s bond lowered from $1,500 to $500.

The charges were later dropped, but the iconic mug shot lives on. Sinatra looks like he was accompanied to jail by his stylist (or at least a mirror). The eyes clear and piercing, forelock hanging jauntily, a tassel of roguish charm. On his sensuous lips, the whisper of a smile. This is the pinnacle to which all mug shots must aspire.

David Bowie, pinched in 1976 in Rochester, New York, introduced a subtle element of stripes. Managing to look every bit the imperial Thin White Duke despite the mundane charge of criminal marijuana possession, Bowie substitutes for the hint of smile an icy stare that seems to say “It’s my world, and you’re lucky to be taking my photograph in it.”

By contrast, in his arrest shot Mick Jagger looks a bit dour, his tie stuffy. He’s not having fun with it. Just 24, Jagger was busted for drugs along with bestie Keith Richards. The Rolling Stones frontman was briefly incarcerated again in 1972 (along with Keith) and looks no better. Jagger, adept at so many things, is no good at getting arrested.

Billy McFarland’s June 30, 2017, mug shot photo.

Seasoned cell-warmer Richards, by contrast,  has been behind bars five times –on par with millennial troublemaker Justin Bieber.  (The Doors’ Jim Morrison appears to be the record-holder, at six.) Unlike Bieber, who grew up in the social media age, high-res mug shots of Richards are almost impossible to come by. Bieber, on the other hand, has spawned meticulously curated jailhouse timelines and “most memorable arrest” articles that detail a variety of looks  — none particularly exemplary– to commemorate everything from drunken drag racing to egging a neighbor’s house and attacking his limo driver.

For one of the photos, we’d swear he was hauled in by the fashion police for an assault on the senses. (We’re not embedding it here, because the Biebs has suffered enough, but we couldn’t resist a link.) We have included one image in which his hair looks pretty great, but also to demonstrate the degradation of digital mug shots (because the mere fact of getting arrested isn’t degrading enough).

Which brings us to 25-year-old William McFarland, founder of the ambitious but ultimately failed Fyre Festival, a planned Bahamian music excursion that was to run April 25 through May 5. Although we think it’s worth a lobbying effort to get real cameras into detention centers (at least for special-occasion celebrity bookings), the fact that McFarland’s image was captured on one of those crummy modern jailhouse units makes it all the more impressive.

As mug shots go, it’s not bad, distinguished by the fact that it looks more like a yearbook photo than a central booking image. Only time will tell if it makes it into the pantheon of classics, but evaluated contemporaneously, it’s not embarrassing. He no doubt seemed presentable to the FBI agents who came to his house on June 30 to take him into custody.

We should probably mention that McFarland was hauled in on suspicion of fraud and scamming investors out of millions. That go big or go home approach makes it likely that there will be a point in the future during which the young serial entrepreneur will not be going home, at least temporarily. But, as Sinatra once crooned, “you’re nobody till somebody arrests you” (or something like that).

Justin Bieber models jailhouse ready-to-wear.

To relate this to the FBI’s own style (if you are aware it has a style), “you need to understand that agents think of themselves as something of a cross between a detective and a spy,” writes Luke Hartig in The Atlantic. “Suits are sharper than those worn by The Wire’s McNulty but still oversized so that a pistol can be easily concealed. Haircuts are short but stylish. FBI agents also love men’s hardware, such as cufflinks, tie clips, lapel pins—little flashes of bling that make the detective into an agent.”

Bling is fine when you’re a free agent, but has no place in prison, where it will be confiscated on arrival and stored for safe-keeping (allegedly). While in custody, it is customary to wear traditional garb, resembling hospital scrubs, similar to the orange outfit seen on Justin Bieber in this 2014 mugshot.

Of course it was Elvis who brought rock ‘n’ roll swagger to the jailhouse in 1957 with his Lieber and Stoller hit. There’s an outlaw myth to rock that mingles with the rough and tumble prison vibe. How the “white collar” element fits into it is something sociologists, musicologists and fashionistas are still figuring out.

Mick Jagger might be a role model, but is not a model prisoner.