31 Pirate Hairstyles for Men: Rugged and Authentic Looks for Halloween

Get ready to hoist the sails and embrace your inner swashbuckler! Whether you’re aiming to rule the Halloween party or set sail at a themed event, these 31 pirate hairstyles for men will add a perfect mix of danger, flair, and authenticity to your look.

From dreadlocks adorned with beads to slick modern fades under bandanas, there’s something here for every aspiring sea rogue. Let’s dive into the rugged world of pirate-inspired hairstyles that’ll have everyone shouting “Ahoy!”

1. Bandana Completely Covering the Top of Medium-Length Wavy Hair

A timeless pirate staple. Medium-length waves covered entirely by a bandana give off a seasoned, practical look. It suggests time spent on rough waters and adds a bit of mystery, as it keeps the hair controlled while still hinting at unruly texture underneath.

2. Bandana Over Medium-Length Hair Heavily Adorned with Beads

For pirates who love to flaunt their treasures, this look lets you showcase your flair. The bandana sits comfortably on medium-length hair decorated with wooden, metal, or seashell beads. It’s bold, festive, and perfect for embodying a charismatic pirate captain.

3. Beaded Dirty Blonde Long Hair with Two Low Braids and Face-Framing Braided Tendrils

This elegant yet wild hairstyle is perfect for embodying a thoughtful pirate with a weathered soul. The dirty blonde shade adds dimension, while the low braids and face-framing tendrils give a structured yet free-spirited look.

4. Bald with Beard and an Eyepatch

Sometimes, simplicity wins. A bald head paired with a thick, rugged beard and a signature eyepatch radiates menace and leadership. This look is ideal for portraying a high-ranking pirate villain.

5. Buzz Cut with Bandana

This neat and modern style combines the sleekness of a buzz cut with a classic bandana. It’s a low-maintenance look perfect for warm environments and portrays a sharp, combat-ready pirate.

6. Buzz Cut with Eyepatch

Another minimalist masterpiece. A buzz cut with an eyepatch evokes danger and mystery. This look screams enforcer or right-hand pirate who doesn’t tolerate mutiny.

7. Classic Dreadlocks with Beads Mixed with Free Hair and a Pirate Hat and Bandana

This bold and expressive style pays homage to iconic pirate looks. Dreadlocks interspersed with loose hair create volume and wildness. Add beads, a hat, and a bandana for full theatrical flair.

8. Classic Messy Long Hair

Nothing says “sea veteran” like messy long hair. Salt-kissed and tousled, this look gives you that untamed and unpredictable charm crucial for an adventuring pirate.

9. Cornrows

Tight and practical, cornrows allow pirates to keep their hair manageable on long sea journeys. This style works well with ornaments or gold thread for added pirate aesthetics.

10. Dark Dreadlocks with Dirty Blonde Highlights Adorned with Beads and Trinkets

Dark dreadlocks with blonde streaks add contrast and personality. Sprinkle in pirate trinkets like keys, coins, or shells for a weathered yet mystical vibe.

11. Evil Clown Pirate Tousled Red Hair with Black Highlights

For those looking to stand out with a more eccentric character, this tousled style with stark red and black contrasts turns heads and adds sinister fun.

12. High Ponytail with Fade Undercut

This edgy and modern pirate look is for the confident buccaneer. The high ponytail keeps hair away from the face, while the fade undercut adds structure and polish.

13. Long Half-Up Half-Down Bun with One Side Tucked Behind the Ear

This look strikes a balance between control and flow. It’s ideal for a thoughtful strategist pirate with a touch of elegance and authority.

14. Long Half-Up Half-Down Top Knot with Multiple Cascading Highlighted Braids

A high-impact style for those who want complexity and creativity. The top knot creates height, while cascading braids add motion and flair.

15. Long Half-Up Half-Down with Few Thin Decorated Braids

Understated yet stylish, this version introduces subtle decorated braids into a laid-back long hairstyle. It adds just enough detail without being too flashy.

16. Long Pushed Back with Beads

An excellent choice for a no-nonsense captain. The hair is kept back, controlled, and accented with a few beads to represent trophies or memories.

17. Low Ponytail

Classic and practical. The low ponytail works with nearly any pirate outfit and gives a mature, responsible air while still being battle ready.

18. Medium-Length Hair with Free Locks Flowing Over a Bandana

This style lets your hair do most of the talking. Medium locks flow naturally over a loosely tied bandana, giving a relaxed and carefree vibe.

19. Messy Half-Braided Long Tucked Hair with Beads

Combining mess and order, this look features a few strategic braids and beads for flavor while the rest of the hair tumbles naturally. It’s a great choice for creative or mysterious characters.

20. Messy Long Hair with Multiple Dutch Braids

Dutch braids add an unexpected element to a long pirate hairstyle. Keep the hair messy for contrast, giving a look that’s both artistic and dangerous.

21. Messy Slicked Back Hair with Wet Look

Perfect for a freshly emerged-from-the-sea pirate. This wet look adds mystery and a cinematic vibe, as if you’ve just won (or lost) a swordfight.

22. Pirate Subordinate Short Tousled Textured Hair

Ideal for background crew members or younger pirates, this short, tousled hairstyle is practical and requires minimal upkeep while still conveying that rebellious energy.

23. Pushed Back Medium Hair with Bandana

Control meets cool. Pushed-back strands stay out of the face while the bandana ties the look together great for strategic minds and stealthy roles.

24. Shaved Sides with Long Hair on Top Styled into High Ponytail

Rugged and warrior-like, this style adds tension and strength. Shaved sides offer a modern twist, while the ponytail maintains the classic pirate vibe.

25. Short Hair Styled into Spikes with Bandana

Add a punk edge to your pirate look. Spiky hair peeking out from a tied bandana gives your character unpredictability and high energy.

26. Simple Side-Swept Soft Wavy Hair with Bandana

Elegant and modest. Side swept waves add softness, while the bandana keeps the look grounded in pirate territory. Ideal for romantics and poets of the crew.

27. Soft Waves with Middle Part and Bandana

Middle parts bring symmetry, while soft waves provide movement. This style blends nobility and edge a refined pirate prince, perhaps.

28. Spiked-Up Mohawk

If you’re channeling a rebellious, rule-breaking pirate, a spiked-up mohawk brings the drama. Add piercings or tattoos to complete the look.

29. Tousled Soft Brown Hair with Dirty Blonde Highlights and Bandana

This earthy, approachable style brings natural charm to the table. Highlights suggest time in the sun, and the bandana finishes it with pirate swagger.

30. Wavy Bob Cut with a Pirate Hat

A rare and stylish cut in pirate lore, the wavy bob is striking and elegant. Top it with a traditional pirate hat to elevate your appearance.

31. Young Inexperienced Pirate Captain Long Fringe Undercut

Perfect for a rising star of the seas, this look features a dramatic long fringe paired with an undercut, showing potential, ambition, and rebellious charm.

Whether you’re aiming for legendary captain, chaotic first mate, or wide-eyed deckhand, these pirate hairstyles will help you embody the role in both style and attitude. Pick your favorite and complete the look with costumes, props, and, of course, the right pirate accent. Halloween is the perfect time to let your pirate persona shine!