As it begins to appear increasingly likely that former President Trump will do a stretch in prison, what should his wardrobe look like? How should the First Felon be attired?

He cannot just go around in a giant orange prison suit—that would be grotesque. On the other hand, Trump must look like a prisoner in a prison, albeit a NICE federal prison and in a presidential way.

Plus, there are policy questions: Can Trump wear the presidential seal? How about his signature red ties that are as long as Lebron’s wide-raised arms? Will his name tag read, “President Donald J. Trump”?

The president would probably insist on adding, “An Innocent Man.”

According to the New York Times, Trump favors Brooklyn’s Martin Greenfield Clothiers, who also dressed Barack Obama and Michael Bloomberg. Perhaps a good tailor could fashion an all-occasion, indoor-outdoor wardrobe that includes a suit, a blazer, dress trousers, golfing clothes, and casual wear.

The Donald won’t require formal wear, as it is unlikely he will be attending any state dinners. But he might want to hold a watch party in his inmate quarters on election night. After all, Socialist presidential candidate Eugene V. Debs garnered nearly a million votes when he was serving a 10-year prison term. Trump might get two or three million votes from fanatical loyalists who resemble Hiroo Onoda, the last Japanese soldier to surrender 29 years after WWII ended. Trump knows lots of Hiroo Onodas.

As to overall style, the president could emulate his pal Kim Jong Un’s Maoist militaristic look, or go full British like his American advisor and former jailbird Roger Stone, whose “dress British, think Yiddish” look makes him the best-turned-out felon since the fictional character Gordon Gekko. The two even shared a tailor—Alan Flusser.

Whatever the style direction, the wheels had better start turning soon, making sure to clear designs with prison officials and ensuring that robust professional facilities for cleaning and pressing the presidential con wardrobe are in place. Everything must be in readiness for the First Felon POTUS.

Finally, who will do Trump’s hair? Prison barbers are notoriously ham-handed and unsubtle, so who will tend to what is left of the president’s locks? One supposes that a stylist could be brought in, but it would be costly, and the American taxpayer should not be expected to shoulder the burden in these uncertain times. If the president does it himself, he will need extra time in the morning to tend to this chore, which is probably why he never got to the Oval Office before 11 a.m when he was president. “Executive time,” as the White House called it.


Bill Huey is president of Strategic Communications and the author of Advertising's Double Helix: A Proposed New Process Model. Journal of Advertising Research, May/June 1999. His article about advertising effects has been cited in books and academic papers around the world.