Jack Gyllenhaal has always been one of Hollywood’s most stylish celebs, but he’s pushing his passion for fashion to an obsessive degree and becoming known far and wide as a bona fide clothes obsessor. An insider exclusively reveals to Life & Style, “On the doorstep of middle age, the funny thing you notice about Jake is how materialistic he has become about his fashion choices and options, like he’s putting way too much thought and effort into it. His favorite pastime is looking at himself in the mirror in a cutting-edge new outfit. He has the right to have a hobby but he’s gone way too deep into it!”

The Road House actor, 43, kicked off 2024 at Milan Fashion Week and made a rare appearance with girlfriend Jeanne Cadieu at the Prada fashion show. Jake has a close relationship with the brand as he was the face of Prada’s fragrance line in 2022.

“His weakness for extreme luxury fashion is a little bit of a joke among the people who have known him since he was in his twenties, when he was happy to roll out of bed in his sweatpants for a lunch meeting. Twenty-five years later and Jake really doesn’t leave his house without checking with his stylist that he’s wearing the latest and the greatest fashions,” the insider adds. “This isn’t about getting his picture taken, either. He’s worn lavish outfits, especially during the pandemic, and never even got seen in them [by publications].”

While it may be materialistic, the insider insists that “Jake’s fashion addiction is purely for himself, not his fans and not his public image. He gets off on wearing the coolest, newest stuff – especially if he gets it for free! It’s a little sad, but this is how Jake blows off steam these days.”

Jack Gyllenhaal ‘Materialistic’ About His ‘Fashion Choices'

The Brothers actor even brought his passion for fashion to Saturday Night Live when he hosted the sketch comedy series in May. One of the skits was a commercial spoof for fast fashion brands. Jake and SNL comedians Ego Nwodim, Chloe Fineman and Marcello Hernandez, portrayed models for the fictional brand, while a narrator described the clothes.

“Modern styles, designer dupes, no prisoners involved,” the narrator said as Jake posed in a jacket and vest combo.

“Why bring that up?” he replied.

In 2021, the Hollywood star took fans along his wardrobe over the span of his career during an interview with GQ.

“Style is self-expression; it’s a representation of your mind. Choosing an idea; choosing a mindset with which you align. Wearing an artist or designer’s work on your body is an expression of your taste and a choice,” he told the outlet, noting, “Style is about the balance between allowing yourself to come through and expressing an idea that you want to reach out to and become.”

The Spider-Man star also explained how his “style has changed” because “with age there comes a different representation of self.”

“I don’t think I take big enough risks when it comes to clothing. I want to look back on my outfits and regret more,” Jake admitted. “I think regretting things you’ve worn in the past is a big part of self-expression, which to me is vital in being human. That leads to you being better today, whether personality-wise or with your clothes.”