Presidents’ Day is coming up, and in order to avoid sounding partisan and getting into a whole thing here, it made us reminisce of simpler times, when a president’s style was something we could ponder due to there not being a constant shitstorm of scandal and controversy (so..almost never.) But as we are the constant gardeners of style and politics is a little bit more than a hobby of ours, we wanted to see which of our Commanders-in-Chief would have made the pages of a GQ or Esquire had they not ventured into their ultimate choice of career*.

So regardless of who of these men that we’ve chosen were “good” presidents or not, or whether they were plagued by scandal, or whether they were Whig, Democrat, Republic, or Bull Moose, we’ve listed our top ten most stylish residents of 1600 Pennsylvania Avenue in all of our nearly two hundred and forty-three years.

John Kennedy

Ah yes, the no-brainer choice. To say that Kennedy was stylish is to say that Kennedy was rich, Catholic, and a Harvard graduate. It was just part of the man’s essence (hold your jokes.) When Americans watched the first televised Presidential Debate in 1960, they saw a tan, relaxed, and confident young Kennedy face off with an older, paler, sweatier Nixon, and the rest was history. He and his brothers’ penchant for Brooks Brothers didn’t hurt things, either.

George Washington

The Father of Our Country was also the father of sharp eighteenth century style. From his fancy colonial military regalia to his presidential suiting, the 6’4″ Washington set the standard for presidential stature, literally and figuratively, in the more than two centuries since his inauguration.

Theodore Roosevelt

The “Trustbuster” and all-around man’s man was such a pillar of Gilded Age style that we featured him as one of our choices for most stylish men of the twentieth century, which you can read here.

Ronald Reagan

Not surprisingly, the only actor-president makes the list. Reagan parlayed his acting career into that of a politician, first as California Governor and then as President during the Wall Street 80s. We still don’t know who he thinks he was fooling with that hair that was ALL BLACK well into his 70s, but as an actor, the man knew that image was crucial to his success.

William McKinley

A big fan of the tuxedo collar and the double-breasted topcoat, the third U.S. President to die by an assassin’s hand also had eyebrows that would give Martin Scorcese a run for his money, which shows boldness.

Harry Truman

One of the early adopters (not named Gandhi) of the round specs and bowtie (come to think of it, he kinda looks like a white Gandhi.)

Barack Obama

Second only to Kennedy in terms of glamour, panache, and charisma, our first black President is also our coolest. He was (and still is) always the best dresser and smoothest guy in the room, so much so that everyone around him would benefit from this via cool-guy osmosis.

Martin Van Buren

Another president that was an early adopter of a now-famous trend, MVB had mutton chops that could dam the Mississippi, long before Portlandians and collector pipe shop owner’s stopped cuttin’ their Mutton.

Gerald Ford*

As we alluded earlier, our 38th President was an actual male model (the original Derek Zoolander,) and was even featured on the cover of Cosmopolitan. If that’s not something that gets you on this list, nothing is.

Abraham Lincoln

To show how influential Lincoln was on men’s style, his signature stove-pipe hat is now know simply as a “Lincoln hat.” You gotta be one bad motherfucker to take something that already exists and have it renamed in your honor, while also making the Dutch beard cool. This paved the way for Beatniks and mid-century Hipsters nearly a hundred years later.

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