Jake Gyllenhaal is an attractive American actor known for his incredibly dynamic performances in films like Jarhead, Zodiac, Donnie Darko, End of Watch, Southpaw, Prisoners and The Guilty. The classically handsome celebrity is not only recognized for his acting skills on the silver screen but also for his stylish and ever-changing hairstyles, which have come to symbolize his masculine energy and fascinate fans.
From a military-inspired short high and tight fade to a modern long flow, Gyllenhaal has rocked several stylish and edgy cuts to suit his personality and look, turning him into a style icon. In this piece, we will explore some of Jake Gyllenhaal’s greatest haircuts, discovering his most memorable and iconic styles.
Jake Gyllenhaal’s Iconic Haircuts
Classic Buzz Cut
In his early years, Jake Gyllenhall showcased a classic buzz cut, a fresh military-inspired style that became a hit in Jarhead. The film may have been the first time the world saw him with a very short haircut, but then he rocked a similar look when filming End of Watch in 2011.
The buzzed masculine cut perfectly suits his facial shape and features, making him look like a true badass. Because his hair is so thick, it likely gets out of hand quickly. If you want to maintain a buzz with thick hair, you’ll need to visit your barber every three to four weeks for a fresh trim.
Undercut
The undercut is a striking hairstyle that complements Gyllenhaal’s thick, longer hair on top. The undercut slick back gave him a mature, dark and attractively rugged appearance in Prisoners, perfect for his role as Detective Loki. His hair is long and brushed straight back on top while the short undercut provides contrast and dimension, delivering a low-maintenance look. The cut is polished but not too refined, making it an excellent choice for no-nonsense men who prefer slightly longer styles.
Long Slick Back
Jake appeared on The Morning Show in 2015 sporting a handsome 50s-inspired slicked back. His medium-length hair featured a barely-there side part with the classic “greaser” texture, a hint of curl at the nape, and the quintessential single strand of hair falling over his forehead, which added to his boyishly handsome look.
The cut is easy enough for guys with relatively straight hair; liberally apply styling gel to damp hair, then brush it straight back while creating the illusion of a side part.
Short Crew Cut with Tapered Sides
In 2010, Jake visited London for a series of media interviews at the Claridges Hotel. He stepped out into public dressed to impress in an impeccable light gray suit and sporting a short crew cut with tapered sides and lots of texture. This low-maintenance cut was perfect for Jake that year, one of the busiest of his career. It’s also ideal for men who want to look like superstars without devoting hours to styling in the morning.
Ask a barber or stylist for a mid-length crew with a close taper down the sides and back. Apply pomade, pull a comb through the top from front to back, then gently lay the hair back down. You can even mimic Jake’s “flip” in the front with a quick comb and a shot of hair spray.
Prisoners Slicked Back Undercut
In Prisoners, Gyllenhaal sports a relaxed and trendy slick back with a clean undercut on the sides and back, creating a rebellious and moody appearance to reflect the film’s dark storyline. His messy slicked-back style rarely looked the same from one major scene to the next and spawned an entire series of masculine looks. Jake’s once-immaculate undercut is clearly disheveled and demonstrates Detective Loki’s frazzled state. Though he looks fresh from the shower, he uses a high-shine pomade or styling gel to achieve the wet look. Some even say he channeled Joaquin Phoenix’s role and appearance as Johnny Cash in this scene.
Southpaw Buzz Cut Fade
Jake Gyllenhaal’s preparation for his role as Billy “The Great” Hope in Southpaw (a role originally intended for Eminem) was intense. He did 2,000 press-ups daily for months leading up to filming to achieve his buff and built appearance, perfectly highlighted with a traditional buzz cut fade. The top section looks like a slightly grown-out buzz, and the fade starts high on the head to reveal a simple tattoo behind the ear. It’s a simple and iconic look that is easily duplicated – except for the muscles. Good luck with the press-ups.
Long Flow
In 2020, Gyllenhaal’s Oscars afterparty look featured naturally flowing long hair and a full beard. He was a heartthrob sporting a classic black suit and glorious long hair with textured ends for a feathered finish. Once again, it’s easy to see just how thick his dark tresses are. He likely applied a light styling cream on damp hair, then used a round brush and blow dryer to achieve the sleek locks on top and the wavy finish in the back. The full and slightly rugged beard was the perfect accouterment.
Jarhead Military High and Tight
Although Jarhead came out way back in 2005, when Jake was much younger, there’s something about the military high and tight and a clean-shaven face that can take years off your appearance. When he played Anthony Swafford, he looked like a teen, but he was 23. Because his hair is so dark and full, you can still see his widow’s peak at the hairline, and the skin fade puts all the attention on Jake’s captivating blue eyes.
Ask a stylist or barber for advice before diving in with the clippers. Facial features and head shape are individual considerations that can play a major role in how the finished cut looks.
Textured Medium Brush Back
At the Spider-Man: Far From Home screening, Jake arrived rocking a charming medium-length brush back with a textured finish to complement his striking blue suit jacket over a green tee. His stylist layered his thick, dark brown hair and then used a blow dryer to sculpt the perfect brushed-back style. He likely used a hair spray with a matte finish to keep the look in place, although sculpting clay could be an excellent alternative.
Long Ponytail
Somehow, Jake looks rugged and polished in a sleek, long ponytail. The different hues in his hair – including dark honey and caramel highlights – stand out against his naturally dark roots. Paired with the dark tortoiseshell shades, a thick, enviable beard, and a simple gray sweatshirt, he looks downright cozy and well-groomed.
Create this style by pulling your hair back into a low ponytail, double looping, wrapping the ends around, and tucking them in to hide the band. Use a small amount of pomade or styling gel to smooth down flyaways.
Textured Short Hair with Cropped Sides
Jake looks impressive in every hairstyle, but many agree that textured short hair suits him the best. The top section of hair flows up and over from a hidden side part, and it blends perfectly into the cropped sides. The quirky texture and fun brush-up in the front give the star a playful look that highlights his personality. Worn with a stubbly beard, it’s a masculine and raw look that is easy to maintain.
Side Swept Ivy League
A sophisticated side-swept Ivy League is a classy men’s hairstyle that takes Gyllenhaal from bohemian and beachy to Wall Street, making him look classically handsome on the red carpet. His caramel-colored tresses are parted on the side and swept up and back at the front. A few stray hairs add some boyish charm. The cropped sides are sophisticated and neat, and the short beard is masculine and sexy.
To achieve this polished and preppy look, ask your barber or stylist for a soft side part, then leave the front section of your hair slightly longer than the rest. After adding a classic taper on the sides and in the back, use some hair gel to sweep the front of the hair up and over to the side.
High Volume Classic Slick Back with Full Beard
The dapper, high-volume slick back is a classic hairstyle for Gyllenhaal when he wants to balance his thick, short beard with a timeless approach. This look requires longer hair in the front and on the sides and slightly shorter hair in the back, offering easy maintenance and styling.
Apply a generous amount of pomade or styling gel to damp hair, then use a comb to move it up and back while creating the signature texture. The versatile cut suits a wide range of face shapes and hair types when worn with a full beard and sideburns.
Long Buzz Cut
Jake Gyllenhall looks incredibly masculine and sexy with a long buzz cut, a style that uniquely suits his full stubble beard and chiseled jawline. After Jarhead, the actor went through the awkward grow-out phase just like anyone else, but his enviable hairline made it much more manageable. The widow’s peak is prominent in his touchably soft and textured hair.
Ask your barber for a clipper cut with a number five length or longer, and feel free to go shorter on the sides or in the back to make it your own. Styling is effortless; apply a dime-sized dollop of pomade to slightly damp hair, then use a standard comb for texture.
The Covenant’s Brushed Back Style with Beard
Jake played Master Sergeant John Kinley in Guy Ritchie’s The Covenant and sported a brushed-back style that became an icon. His medium-length hair sweeps back and away from his face, and a few waves at the nape paired with a full beard add masculinity and character to his look. It’s a simple, casual, and relaxed style for guys with thick hair.
Military High and Tight Fade
Jake’s military high and tight fade involves a buzzed top with short skin faded sides to complement the cut. The style shows off his hairline and focuses on his beautiful brows. Here, he’s wearing it with a slight hint of stubble for a baby-faced look that is still sharp and masculine.
Young Gyllenhaal without Beard
You’ll rarely see Jake Gyllenhaal without a beard, but he often sported a clean-shaven face when he was young. He wore a dapper gentleman’s cut that’s swept up and back with scissored sides, and along with his crinkle-eyed, dimpled smile, he became one of Hollywood’s hottest up-and-coming actors. Times have certainly changed and while the celeb is in his mid-40s, the iconic and textured haircut lives on.
Layered Pull Back with A Thick Beard
A sleek and slightly tousled layered pull back is signature Jake Gyllenhaal, blending sleek sophistication with tousled masculinity. His hair flows straight back and slightly off to the side, and the scissored sides lend the cut fullness. The hair at the nape curls slightly under, and a bit of messiness at the sideburns blends beautifully into the thick beard.
Ask a stylist for longer layers in the front and a layered scissor-cut taper at the sides. Then, apply a high-shine pomade, tuck the sides back behind the ears, and brush the front portion straight back, allowing some strands to fall to the side naturally.
Thick Buzz Cut with Mid Taper and Stubble Beard
Jake’s thick buzz cut is growing out from his early years. Similar but longer, the mid taper seems shorter at the side than in the back. The result is a shapely buzz cut that looks phenomenal on 30-something Jake, especially when he wears it with thick stubble and a beaming smile. He likely applied a texturizing pomade and used a comb to stand his hair up in the front and on top.
Textured Medium Flow
The difference between a textured medium flow and a brush-up lies in the texture and movement. Jake’s layered locks are longer in the front than in the back or on the sides, and his barber likely used a razor to achieve the beautiful movement in the cut. A tiny bit of sideburns just in front of the ear balances the look, and the stubbly facial hair adds visual contrast that pulls everything together.
Bald Shaved Head
Believe it or not, Jake even fooled the LAPD into thinking he was a real police officer when filming End of Watch. He donned a completely bald, shaved head, and according to his co-stars, he wasn’t apprehensive at all. A fully shaved head involves a razor, but you can get close with clippers. Stylists and barbers agree you’ll want to stock up on some supplies if you plan to maintain the cut, including a cloak and a razor for finishing off any bumpy spots the clippers miss.
