EXCLUSIVE: Secrets of Brad Pitt's 'Midlife Crisis' Makeover Revealed — After He Makes Shock Admissions About Alcoholism and Gay Sex

Brad Pitt saw the question coming as he and girlfriend Ines de Ramon made a rare red carpet appearance together at the June 16 premiere of his movie F1 in NYC's Times Square, RadarOnline.com can reveal.

"You've been rocking some really cool outfits, and we're GQ," a reporter from the men's fashion bible began.

The 61-year-old smiled knowingly as the reporter asked him the inspiration behind his new look. "I just feel like, you gotta have fun," Pitt replied while waving to the crowd. "I mean, let's have fun. There's so much turmoil in the world, let's have fun when we can."

For days, the actor, with a newly shaved head, had been stepping out in uncharacteristically garish outfits: a silky lilac Taverniti shirt and loose pajama pants printed to look like whiskered jeans for a double date with Bradley Cooper and Gigi Hadid at NYC's trendy Cote Korean Steakhouse; a Willy Chavarria crushed velvet jacket and oversized jeans for dinner with de Ramon, 36, at the Greenwich Village hotspot Carbone June 14. The looks prompted one news outlet to ponder: "Is Brad Pitt Having a Midlife Crisis?"

He has every reason to be.

As RadarOnline.com has previously reported, the actor has virtually no relationship with the six children he shares with ex Angelina Jolie after the former couple's yearslong, bitter divorce. His movie F1 has a reported budget of $300million – one of the most expensive films ever made – putting him in the hot seat in terms of getting audiences to theaters.

Add to that a decades-younger girlfriend – no wonder the guy wants to have some fun.

"It's common knowledge how devastated Brad is to be estranged from his kids right now, and there's a lot of pressure on him for this movie to be a success," an insider told RadarOnline.com. "A lot of people think he's just doing whatever he can to appear cool and relevant."

For starters, that meant working with, among others, the stylist who duded up none other than Timothée Chalamet for his eye-catching promo tour for last year's A Complete Unknown.

Taylor McNeill, the stylist, was also responsible for putting Kendrick Lamar in flared jeans for his Super Bowl halftime show.

But what might work for a 29-year-old doesn't necessarily translate to a man twice his age.

That lilac top veers close to "puffy shirt" territory. "Brad feels younger and more hip wearing these things," said our insider. "To a lot of people, though, this reeks of a midlife crisis, like he's trying to overcompensate, and he's making himself look pretty lame in the process."

As for his shorn locks, the star told another reporter it was for a role. "I just finished a job, a character I did," he explained, apparently referring to House of the Beast, his only project in post-production. But an insider told RadarOnline.com he may be dealing with yet another midlife concern.

"Brad is obsessed with keeping his hair in its best possible condition," said the insider, noting it was trimmed and its color touched up twice weekly during the long F1 shoot.

Added a second insider: "His hair was put through the wringer and he wanted a fresh start."

With de Ramon, a jewelry company exec, taking on a more public role in his life, there is widespread speculation about whether Pitt will put a ring on it. Certainly, the twice-divorced star couldn't be blamed if he soured on marriage altogether.

Yet he seemed unemotional when discussing the drama of his nearly 10-year legal battle with Jolie over custody of the kids, including accusations of abuse, which he has denied, as well as ownership of the French winery Château Miraval.

Asked if he felt any relief after the divorce was at last being finalized, he was nonchalant. "No, I don't think it was that major of a thing," he told GQ. "Just something coming to fruition legally."

He also told the mag he was content.

"My life is fairly contained," he said. "It feels pretty warm and secure with my friends, with my loves, with my fam."

At the same time, however, he's never been more distant from his kids. Maddox, 23, has virtually disowned him, Zahara, 20, and Shiloh, 19, have dropped 'Pitt' from their last name and Pax, 21, who was recently spotted looking worse for wear while partying with friends, called him a "world-class a**hole" in a since-deleted 2020 Father's Day post.

That leaves his minor children, twins Vivienne and Knox, 16, as the only kids legally required to see him.

"It's a pivotal moment," said an insider. "He knows this may be his last real chance to rebuild a connection."