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Chillin' in Neutrals: How Jake Gyllenhaal Owns His Style

Writer's picture: Tom GoedhartTom Goedhart

Before we dive into Jake Gyllenhaal’s fashion choices, let’s take a moment to acknowledge his incredible talent as an actor. He’s not just one of my favorites - he’s undeniably gifted. From his breakout role as the awkward teen in Donnie Darko to portraying a gay cowboy in Brokeback Mountain, and the gritty boxer in Southpaw to the morally ambiguous journalist in Nightcrawler, Gyllenhaal has showcased remarkable range. Most recently, he wowed audiences as Mysterio in Spider-Man: Far From Home.


Just as diverse as his filmography is his personal style. Jake has experimented with a myriad of looks, from minimalist basics - which he favors - to unexpected accessories that keep his wardrobe fresh and engaging. Yet, no matter how adventurous he becomes, his smart color choices ensure he never misses the mark. 

Basic outfits and minimalist colors remain a favorite and daily dressing habit of Jake Gyllenhaal. The classic combination of white and navy blue continues to be a timeless duo for men. Basic doesn’t mean boring; pay attention to the harmony achieved by combining pinstripe patterns on a blazer with the distinctive texture of linen from a T-shirt. 

Just by wearing what you love, confidence will come naturally without needing anyone to push you.


Still keeping the spirit of simplicity, but when you need to dress up a bit more, it looks like this.


Jake understands the versatility of a plain white T-shirt perfectly.


It’s still a white shirt and a navy blazer, but the button-up shirt adds a level of seriousness that a T-shirt doesn’t provide.


Frequently donning neutral colors, Jake lets the accessories take center stage, showcased here with the Cartier Santos watch.


All-black!


Once again, the focus is on accessories, highlighted by the eye-catching gold necklace.


Switching to a workwear style with a looser, more comfortable fit, featuring a white jacket, gray chinos, and black work boots.


Then he suits up in elegance. When it comes to suits, Jake has plenty of tricks up his sleeve. Here, he sports a gray suit paired with a crisp shirt and a perfectly tied tie.


Then one day, he decides to mix it up by pairing a suit with a turtleneck sweater.


Then he adds some personality with bold patterns like this. The white T-shirt plays a balancing role, ensuring nothing goes overboard.


This is perhaps the moment when Jake Gyllenhaal surprised everyone by wearing a glossy silk pajama underneath a coat.


With numerous experiences and combinations, one common trait in Jake's outfits is the lack of excess; he simplifies every detail.


These images summarize Jake's style over the years. And if you’re wondering how Jake looks now, here he is during the recent lockdown.


Still looking very "on fire," right?

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