Trump has had a lot of interesting moments with his red MAGA hat

Donald Trump's Make America Great Again hats have been a cornerstone of the former president's political identity since long before he was elected to office. Trump's MAGA hat turned into an important political statement for his followers and it hasn't lost any steam over the last near decade.

However, in all of that time, the former president has sported his red cap atop his noggin in a lot of questionable ways. Here are Trump’s best and worst moments in a MAGA hat as well as a bonus shot at the end that will make you rethink everything you know about him. 

The 2016 campaign was probably the high water mark of the former president's love affair with his red MAGA cap, and we got a lot of great photos of Trump looking like a goofball underneath the hat that would become the future symbol of his political movement.

Photo Credit: Wiki Commons By Gage Skidmore, CC BY-SA 3.0

But Trump didn't always look ridiculous in a MAGA hat. This shot captured at a campaign rally in Fountain Hills, Arizona actually made future President Trump look like an adorable old man. Well, if you can get past all the racist comments and terrible things he said to win the GOP nomination.

Photo Credit: Wiki Commons By Gage Skidmore, CC BY-SA 2.0

This picture of Trump back before he was nominated to be the 2016 Republican presidential candidate showed just how cool the former president could look while furiously complaining to a crowd in his signature MAGA hat. Note the hair awkwardly flowing at the back; it's a recurring theme...

It seems no one ever told the former president just how bad he looked in profile while wearing a MAGA hat, as this image from 2023 shows. Nearly a decade later Trump was still letting his hair flow out the back untamed and wild.

Modern photos of Trump sporting his signature red cap certainly have helped put the former president's age in focus. Without all the alleged makeup and prep work for the cameras, he kind of looks like he wouldn't be able to handle another four more years.

The MAGA hat can help reveal Trump's true awkward nature as well. Back when he visited East Palestine after a train derailment, this shot of him next to cases of fresh water for residents of the town gave onlookers a glimpse of that icky side of Trump's demeanor the world rarely sees.

This shot of the former president at a rally for his former political rival Marco Rubio in Miami gave us one of the first and only glimpses we got of Trump from behind while wearing a MAGA hat. Spoiler, it looks weird and offputting.

Sometimes Trump's red cap can really bring out the expressions in his facial features. This is especially true when photographers get close enough to catch the former president in an awkward light. This shot from Bedminster with Yasir al-Rumayyan, the head of Sadi Arabia's Foreign Wealth Fund is a good example.

Different event but the same awkward Trump at a golf course. This might be the single worst shot the former president has ever taken in a MAGA hat and it's been used relentlessly by the media to show their audiences just how unfit Trump has become for the presidency.

Trump likes to sport the same outfit when he's playing golf. His trusty red MAGA hat is always on his head. He also loves to give free hats away when the mood strikes him. It's an interesting way to keep pushing the myth of the MAGA cap as a means of political symbolism.

Trump in profile from far away with a MAGA cap on is just as bad as the former president from behind. Somebody on his team needs to let him know that he should only be photographed from the front when sporting his politically unpalatable hat.

Golf course Trump strikes again but this time his bright red cap is only working to accentuate the full girth that the former president had taken on in the years after he left office. Not that he wasn't a big boy before eating all that fast food and drinking all those sodas while in the Oval Office.

However, Trump actually can take a good picture in a MAGA hat. This example was taken in 2021 as Trump was returning to Trump Tower and it shows just how imposing and intimidating the former president can look when sporting his signature red cap.

The MAGA hat can also look really good while on campaign in the former president's post-White House days as this shot from 2022 can attest. Trump actually looked quite sharp at this rally in Florence, Arizona.

Sometimes Trump's MAGA hat can give the former president the air of a supervillain, as this downright scary shot of him at a rally in North Carolina in 2020 showed. The black gloves and red cap really work together to transform Trump into a Lex Luther-type.

The former president can even look downright presidential at times. But it is quite a clashing fashion statement to be wearing a red ballcap with his signature black overcoat.

Nevertheless, Trump's red MAGA hat is one that his core supporters love to showcase when in public or at one of his events. Take for example this couple who really seem to buy into the power of the former president.

If Trump's supporters are lucky, they might even get a signed hat from the former president, something that he loves to do for his adoring fans when his supporters bring one of his red MAGA hats to him.

You probably didn't know that Trump actually does wear hats that aren't in his signature red. On January 14th, 2024, Trump wore a white caucus hat, presumably in order to bring a little extra attention to his primary campaign while speaking at an event.

We couldn't end this list without showing you the greatest picture of Trump in a MAGA hat. There's something about this shot from behind that screams "Trump," and it's not the fact that his name is emblazoned on the back of the hat. It's the combination of hat, hair, and suit color that is quintessential Donald Trump.