Times Trump Tried (& Failed) To Hide Botched Makeup & Signs Of Aging With Tacky MAGA Hats

When he took office, President Donald Trump made it clear that he lives by his own rules. This includes sartorial ones. Presidents traditionally aren't supposed to wear hats in public, yet Trump does so anyway — and often. It was understandable he would wear tacky self-promoting baseball caps during his campaign; ever the marketer, Trump often gave out samples to supporters at rallies. Yet, even after taking office, Trump has continued not only to wear the hats but also push others to do the same. To mark his 100th day in office, he held a cabinet meeting in which every member was given a "Gulf of America" cap. And, following a critical conference about the war in Ukraine, Trump forced European leaders to tour the MAGA gift shop he had installed in the White House. (No, we don't know whether Volodymyr Zelenskyy went home with a "4 More Years" hat.)

Apart from sending a "na-na-na-na-na-na-LEADER!" message (thank you, "Simpsons"), Trump's hats have a practical purpose. By hiding the top half of his head, Trump can fight his losing battle against balding a little longer, and his makeup fails are a little harder to see. Note we said "a little." There have been plenty of occasions during which the president's headgear wasn't enough to cover up the signs that he's approaching his ninth decade. We offer just a few of the examples here.

For Donald Trump, a casual day consists of going without a tie or makeup and shading his eyes with one of his narcissistic caps. It's a look he adopts most often when he goes golfing, but he's been known to sport the style at press conferences, as well. In his case, the attempt at looking relaxed just makes the president look fatigued and older. As illustrated in the photo shown here, the huge MAGA message only goes so far to take the eye away from Trump's visible pores and dreaded turkey-neck bands.

Attending the opening of his eponymous golf course in Scotland, the president popped on a "USA" cap (just in case anyone might be confused about where he comes from). The topper disguised almost all of Trump's thinning coif, except for the very visible strands over his neck. Alas, Trump didn't use his gold shears to give himself a trim after cutting the ceremonial ribbon. He also appeared once again to do without the pancake coverage, making him appear, as the Scots say, pure done in. 

Speaking to reporters on August 22, 2025, Trump appeared to have enjoyed some late summer sun. A closer examination, however, shows his golden glow is just another makeup smear job. Note the paler patches on his upper cheeks and the outer edge of his neck, and, as usual, he skipped the ears altogether. He does look somewhat more youthful with the foundation on, but the inexpert application destroys the entire effect. The baseball cap may have disguised some of the errors, but Trump made the mistake of looking upward and revealing the truth.

A closer look at Trump's August 22 appearance reveals something even more off-putting about his face. The top of his nose, along with the visible portions of his forehead and eyelids, are considerably darker than the rest of his face. Is this attributable to the remnants of a sunburn he got on the back nine, or did he just apply more of his foundation to that area? Whatever the case, it looks sloppy, and definitely disproves the "right about everything" message on his cap. 

Following his meeting with the Ukrainian president and other foreign leaders in February 2025, Donald Trump appeared before reporters in a hat commemorating both his terms in office. As usual, the low brim couldn't conceal the very visible difference between the bronze shade of his cheeks and the pallor of the rest of his face. We're still trying to figure out the reason behind this common Trump makeup fail. Maybe he just doesn't like the extra effort it would take to rub a makeup wipe over his ears?

The president never admits to being embarrassed, but in this pic, he's certainly red-faced. In a rare makeup-free moment from April 2024, Trump attempted to shade his blotchy complexion with one of his caps, but a low brim can only do so much. Despite his insistence that he's in fantastic shape, Trump's health has seemed to be in decline in recent years, with his bruised hand being the most obvious example. His red patches, however, are nothing new; back in 2016, his medical report revealed he has rosacea, a chronic but harmless skin condition. 

President Trump is seen here speaking to reporters from his golf cart during a summer 2023 outing. Normally, he forgoes the bronzer when he's on the links, but looking closely, it appears he dabbed some foundation just on his rosacea-prone areas, leaving the rest of his skin slightly ruddy. The effect is just about as subtle as a teen wearing acne patches on prom night, but perhaps Trump thought people would be too awed by his signature hat to notice.

Right after attending Pope Francis' funeral in April 2025, the president went to New Jersey for a round of golf before heading back to the White House. Trump's jarring makeup-free look put his true age on blast; without bronzer, his drooping chin and neck become more prominent. On closer examination, the area below his chin appears paler than the one above; it's as white as his ever-present cap. It wouldn't surprise us if Trump uses foundation to give himself a faux jawline and take attention away from the sagging areas.

Most recently, Trump looked every bit his age in late August 2025, when he entered his motorcade with grandchildren Kai and Spencer Trump for a golf outing. The president hadn't been seen in public for several days, sparking theories about his health, but his reappearance made him look to many like a housebound grandpa being taken for a drive. As one commenter on X put it, "Trump walking around with a gaping mouth, obvious rapid hair loss, and eyes damn near swollen shut is certainly not 'prime form'."

It's alive. pic.twitter.com/Ch7T8QQzpa

— Molly Ploofkins (@Mollyploofkins) August 30, 2025