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Here's Why It Look So Weird When Donald Trump Wears Hats

by Solomon Gustavo
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When President Obama wore a tan suit to a press conference in 2014, people freaked out. HuffPost editor Amanda Terkel tweeted “I can't hear what Obama is saying over his suit,” while Washington Post reporter Wesley Lowery asked, "Who gave President Obama that old church suit from my dad's closet?" According to a lot of people on the internet, seeing our our president appear in a light-colored suit was thoroughly distracting.

However, as we’ve been discovering over the past few months, there are weirder things a president can wear than a tan suit. He could also wear hats with his own branding on them, as Donald Trump is frequently photographed doing. Throughout campaign season, Trump's red “Make America Great Again” baseball hat was ubiquitous — but after he took office, it became clear that the hat was no mere piece of campaign swag. Trump often wears hats while attending to his presidential duties; he even wore a cap this past week, while visiting Texas in the wake of Hurricane Harvey.

Though there is a lot more to discuss about Trump's Texas visit beyond his hat, the president wearing a USA snapback with the number 45 on the side, as if the country is a sports franchise with 45 championships, was striking to many. “Amid Harvey, Trump eschews typical presidential optics for Trumpism,” Rick Klein wrote at ABC News, in an article illustrated with images of a cap-wearing Trump; editor Gabriel Howard tweeted, “For a third time, Trump is using Hurricane Harvey as product placement for a hat he sells for $40,” referencing the fact that the hat is available for purchase on Trump’s re-election campaign website.

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Trump's hats look weird for a lot of reasons, not least among them that modern presidents, as a rule, don't really wear hats while on the job; the president’s head is the dome of authority. "Here's the general rule: You don’t put stuff on your head if you’re president ... That’s Politics 101. You never look good wearing something on your head,” President Obama commented in 2013, as a way of rejecting the Navy football team’s request to put on one of their helmets. This tradition makes Trump’s tendency to wear baseball caps all the more distracting.

To put Trump’s snapback love in context, here's some presidential hat history.

The Colonial Tricorn Era

The tricorn hat is part of our collective image of George Washington (1789-97), like how a Kangol is permanently fused atop Samuel L. Jackson in our minds. But actually, all of the first five presidents rocked them. That's because in colonial days, the tricorn hat was worn by all classes of civilians and was also part of military uniform at all levels.

James Monroe (1817-25) had the nickname ‘Last of the Cocked Hats’ because he was the last of the presidents to have fought in the Revolutionary War (aka the 'cocked hat' days).

The Top Hat Era

William Henry Harrison (1841-1) wore a beaver hat. Yup, a beaver hat. The image was so potent, it haunted Harrison’s grandson, President Benjamin Harrison (1889-93); people called grandson Harrison "Grandfather’s Hat," which is probably the best hat-related, perfectly petty presidential nickname of all time (Harrison's campaign wasn't above cashing in on the association, using “Grandfather’s Hat Fits Ben" as a campaign slogan).

And, of course, there is Abraham Lincoln (1861-5) and his iconic top hat, which seems to grow on his head, like a Canadian Mountie cap on Pharrell. Lincoln is said to have worn a crumpled hat to campaign speeches as an endearing, frontiersman political imagery ploy — one that appears to have worked. The hat always brought him attention, and he will forever be first and foremost in our minds when thinking about the very specific subject of presidents and hats. Well, until now, maybe.

The Stetson Era

The Stetson-style hat Ulysses S. Grant (1869-77) is known for was designed for civilian field wear; while he was a general, an observer described Grant in his trademark hat as an “ordinary, scrubby-looking man, with a slightly seedy look, as if he was out of office on half-pay.” The hat doesn't seem like a ploy; in fact, it makes him look like he wouldn't be the kind for such ploys — which is exactly the ploy the hat is supposed to suggest.

The End of the Hat Era

The most iconic image of Theodore Roosevelt (1901-9), where he sits atop a horse, shows the "rough rider" wearing a pinned military cap. However, just a few years later, Calvin Coolidge (1923-9) brought the age of presidential headgear to a close.

In 1927, Coolidge was photographed in a Sioux headdress. When advisors suggested that it was a bad idea, he replied that “Well, it’s good for people to laugh, isn’t it?” The negative press for this incident is often thought to be the source of the “no hats on presidents” rule (though somehow, Coolidge would not be the last president to try this particular move).

However, it still took a few decades for presidential hats to fall completely by the wayside. Though many believe that John F. Kennedy (1961-3) was the first president not to wear a hat to his inauguration, there is photographic proof that he did; the true end of the hat era came when Lyndon B. Johnson (1963-9) opted not to wear a hat during his inauguration.

The Post-Hat Era

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After hats stopped being part of the standard presidential wardrobe, they became effective signifiers of the president’s personality — especially because they were mainly worn while off the clock (and mainly used to signify one's cowboy-ish qualities).

Johnson wore a cowboy hat whenever he could dress casually, and Ronald Reagan and George W. Bush both worked the cowboy hat vibe hard, as well. Gerald Ford must be the only president caught in the Russian Ushanka (still waiting for a Trump image leak, though). Richard Nixon and Jimmy Carter both wore Native American headdresses, and Obama wore a ceremonial hat briefly during a 2016 Tribal Nations Conference, which he got a little flak for.

Which brings us to Trump. His tendency to wear “Make America Great Again” campaign hats during his presidency breaks sharply from past presidential hat traditions, because even when hats were fashionable, they were blank. Trump’s hats, meanwhile, are branded with a slogan or the number 45.

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Trump is the first modern president to have a hat connected to him, which makes a certain sense — he’s fixated on flouting presidential traditions, and it serves as part of his ability to relate to his base, a nod to his nonconformist pseudo-populism. But it also undermines the image of president. It’s tough to inspire confidence in a nation when you’re wearing a snapback from the mall — especially if it has your own logo on it.