What Donald Trump Jr. Looks Like Without His Signature Slicked Back 'Do
There are benefits to having a trademark hairstyle, such as making a person instantly recognizable. It's why we can probably pick out Donald Trump Jr. from a crowd, even among Wall Street finance bros. He has sported the same slicked back do since the mid-2000s, and though it's aging Don Jr. just as much as his patchy salt-and-pepper beard, this likely won't change anytime soon. It's his go-to look for red carpets and political events, including his father Donald Trump's presidential inaugurations. However, he apparently can't stop slicking back his brunette locks with what looks like an entire bottle's worth of hair gel, even when he's spending quality time with his kids at home.
Instagram photos of Don Jr. celebrating Thanksgiving, the New Year, and birthdays with his five children from ex-wife Vanessa Trump gave major "business meeting" vibes due to his signature ultra-groomed look. Thus, we almost couldn't recognize the Trump Organization executive when, in a rare moment, he decided to figuratively let his hair down (and literally mess it up) for a getaway with his kids and his girlfriend, Bettina Anderson.
In March 2025, Don Jr. took to Instagram to share photos and videos of himself and four of his children — Donald III, Tristan, Spencer, and Chloe — enjoying one of their favorite activities: fishing. "Spring break spearfishing crush fest with the little (and not so little) people," the father-of-five wrote as the caption to snaps and clips of him, the kids, and Anderson goofing around on a boat, swimming in the ocean, and showing off what they caught. Instead of his usual perfectly groomed hair, a smiling Don Jr. sported wet, tousled curls, finally looking like a regular dad doing regular dad things instead of his usual business elite persona.
Don Jr. once let his youngest daughter Chloe give him new hairstyles
Donald Trump Jr.'s 2025 fishing trip wasn't the only time he disrupted his slicked-back do. In 2023, he posted photos and clips to his Instagram showing his youngest daughter, Chloe Trump, acting as his hairstylist and giving him some cool new looks. In the first clip, Chloe used her hands, and likely copious amounts of hair gel, to style her dad's locks into long spikes. When Chloe asked if he "like[d] his new haircut," the father of five gave his punk makeover a nod of approval, saying, "It's a good look, really." In the following snap, Don Jr. continued to show off his spiky hair while giving the camera his best supermodel pout (above left).
However, Chloe apparently didn't stop there, also giving her father a '90s-style middle part that reminded us of the Backstreet Boys' Nick Carter. Don Jr. also sported what looked like a severe case of bed head (above right) and more artfully tousled locks in the other pictures. "Great weekend with the smurfs," Don Jr. captioned the post, tagging his then-girlfriend Kimberly Guilfoyle. He added, "Chloe was working on my newest hairstyle so I can complete my Blue Steel look once and for all. ... Thoughts on the look???"
It's unclear if Guilfoyle loved these hairstyles on him or not, but they were definitely a step up from some of the terrible looks he sported in the past. Long before he started exclusively slicking back his hair, Don Jr. used to wear his locks long and wet, making his head look like a greasy nightmare. We'll take the boy band hair over the Severus Snape cosplay any day.