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Every Jake Gyllenhaal Haircut To Try In 2025

Every Jake Gyllenhaal Haircut To Try In 2025
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Interview: Miles Joyner | Crime Fiction Lover
Interview: Miles Joyner | Crime Fiction Lover
Published on 20 March 2025


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In Hollywood, it’s not uncommon for leading men to change their hair like they can’t decide what to have for dinner. Jake Gyllenhaal, however, is the exception.

Unlike his silver screen rivals, the California native has kept his locks fairly constant throughout his career. Sure, it’s been short and severe for his role as a bruiser boxer in Southpaw, and long-locked for a turn as the adopted son of a king in Prince of Persia. But for the most part, the classic Gyllenhaal cut revolves around a soft, mid-length cut swept back, perfectly designed for his oval face shape.

It’s a classic hairstyle, one that will work well in the office, but isn’t too boardroom stiff to stop it looking cool when cutting shapes on the dance-floor at the weekend.

To help you make like Jake on the hair front, we spoke to Stevie Warwicker, a top stylist and manager of Ruffians barbers in London to find out how.

Boy Next Door

Let’s face it, Gyllenhaal is a good looking guy, but this is truly a case of a haircut working overtime for its wearer. Framing his face to perfection, the softer finish balances out his chiselled and well-defined features, including that cut-from-granite jawline.

So how do you copy the look? “Ask your barber for a medium-length scissor cut and keep the softness around the ears,” says Warwicker. “Make sure you maintain length on top so that you’re able to push it back when styling. Then, when getting ready in the mornings, just blow dry the hair backwards using a vent brush and a nozzle to maintain the smoothness and allow the hair cuticles to lay flat.”

Jake Gyllenhaal Hairstyles

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Ready In Five

Men’s hair has been getting progressively longer in recent years, buoyed no doubt by the cherub good looks of Timothée Chalamet and a general loosening of workplace regulations. However, getting in on the act does mean committing to taking longer to get ready and less time in bed. So if you’re not a get-up-and-go kinda guy, consider a classic short but smart cut instead.

“A haircut with a textured top allows for the length to be kept without staying too soft,” says Warkwicker. “Ask for a clipper back and sides around a grade three and for it to be cut shorter and textured on top. When styling, just give it a quick rough dry with the hairdryer and a light bit of product such as styling paste to finish.”

Jake Gyllenhaal Hairstyles

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That Job Is Mine

Got a big job interview coming up and want to impress? Grab a pen and paper, because you’ll want to take notes. This is a polished cut that works with pretty much any face shape and will let the interviewee know exactly who’s the boss.

“This is a simple scissor cut with a side parting that you can’t go wrong with,” says Warwicker. “Ask to keep the back and sides squared to create a more pronounced look and just blow dry the hair backwards, using a vent brush and a nozzle to maintain the smoothness while creating volume and allowing the hair to set in one direction.”

Jake Gyllenhaal Hairstyles

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Freshly Slicked Back

Slicked-back hair has a bad rep thanks to big money Gordon Gecko types who’ve made it their calling card. But for every Eric Trump, there’s a Gyllenhaal showing you how to bring the look back from its 1980s transgressions.

When in the barber’s chair, Warwicker says to ask for a simple, “square medium-to-long scissor cut.” Styling wise, it’s a hard one to get wrong. “This is a wet look and not too difficult to style. Towel dry the hair once out of the shower and add a styling paste or pomade while still wet.” Add a neat beard for some much-needed ruggedness and you’re good to go.

Jake Gyllenhaal Hairstyles

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The Knockout Cut

Gyllenhaal’s signature mid-length cut would never have worked for his gritty role as boxer Billy ‘The Great’ Hope in Southpaw. Instead, this harsher buzz cut works to accentuate the actor’s angular features, so is one to steal if you too have cheekbones you could hang a coat on.

“Ask for a grade three on top and a mid fade between a 1 or 0.5 on the sides,” says Warwicker. “No styling is necessary, however, if you do want some definition a small amount of styling paste will work. For the beard, use a trimmer between a 0.5 and a 1 on to keep with the rugged look and give some shape to the face.”

Jake Gyllenhaal Hairstyles

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