Swashbuckling Pirate Hairstyles for Men: Conquer Halloween with High-Seas Style
Set sail for a Halloween adventure with these rugged, authentic pirate-inspired hairstyles. Whether channeling the notorious Blackbeard or the charming Jack Sparrow, these seafaring styles will complete your transformation into a fearsome buccaneer.
From weathered dreadlocks to roguish ponytails, we’ve gathered pirate hairstyles that balance historical authenticity with modern styling techniques.
The Weathered Captain
The Style: Medium-length hair tousled and textured to look windblown, with subtle layers and a slightly unkempt appearance.
How to Achieve It: Apply sea salt spray to damp hair and scrunch while air-drying or use a diffuser. Finish with a light pomade rubbed between fingers and applied haphazardly for piece-y texture.
Best for: Men with straight to wavy hair of medium thickness. It complements oval, square, and rectangular face shapes.
Sparrow-Inspired Beaded Dreadlocks
The Style: Shoulder-length partial dreadlocks with colorful beads, coins, and trinkets woven throughout, inspired by the infamous Caribbean pirate.
How to Achieve It: For temporary Halloween wear, use dreadlock extensions or create faux locs with wool roving and hair wax. Add beads to the ends and secure with elastic bands.
Best For: Men with medium to long hair who can incorporate extensions. Works well with all face shapes, particularly oval and heart.
The First Mate’s Slick-Back
The Style: Hair slicked straight back with visible comb marks, giving a wet, just-emerged-from-the-sea appearance.
How to Achieve It: Apply strong-hold pomade to damp hair and comb straight back from the forehead. Don’t worry about making it perfect—pirates aren’t known for their tidiness.
Best For: Short to medium-length straight or wavy hair. Particularly flattering for round and square faces, as it adds height.
Blackbeard’s Wild Mane
The Style: A voluminous, untamed style with hair sticking out in various directions, paired with a matching wild beard.
How to Achieve It: Tease hair thoroughly at the roots, then apply hairspray liberally. For extra authenticity, lightly dust with baby powder or temporary white hairspray for a weathered, aged look.
Best For: Medium-length, thick hair with natural wave or curl. Works with most face shapes, especially those that can carry visual weight around the face.
The Bandana Hawk
The Style: Hair shaved or trimmed short on the sides with longer length on top, partially covered by a patterned bandana tied at the back.
How to Achieve It: Ask your barber for an undercut or high fade with 3-4 inches left on top. Style the top with texturizing paste and secure a bandana around the head, letting the top hair peek through.
Best For: Works with most hair types and adds structure to round or oval face shapes.
The Castaway Shag
The Style: A medium to long layered cut with pieces falling around the face and neck, giving the impression of months stranded on a deserted island.
How to Achieve It: Ask for long layers throughout and use fingers to apply styling cream to damp hair. Allow to air dry for maximum texture and separation.
Best For: Medium to thick hair with natural wave or curl. Softens angular face shapes like squares and rectangles.
The Buccaneer’s Ponytail
The Style: A simple low ponytail, slightly messy with strands pulled out around the face, secured with a leather cord instead of a modern elastic.
How to Achieve It: Gather hair at the nape and secure with a thin leather strip. Pull out a few face-framing pieces and rough up the top with fingers for an authentically disheveled look.
Best For: Medium to long straight or wavy hair. Universally flattering for most face shapes.
The Quartermaster’s Queue
The Style: Hair pulled back tightly and braided into a single plait down the back, historically worn by many seafarers for practicality.
How to Achieve It: Apply styling gel at the roots for a slick look, then create a tight three-strand braid. Secure with twine or leather cord and fray the end slightly.
Best For: Medium to long hair of any texture. Particularly complements diamond and heart-shaped faces.
The Marooned Mullet
The Style: Short on top and sides with length at the back—the original practical pirate cut, keeping hair out of the eyes while protecting the neck from the sun.
How to Achieve It: Ask your barber for a modern mullet with textured top. Apply sea salt spray and tousle for an authentic shipwrecked look.
Best For: Straight to wavy hair of medium thickness. Works well for oval and rectangular face shapes.
The Privateer’s Pompadour
The Style: A higher volume front with sides slicked back, reminiscent of 18th-century gentlemen who turned to piracy.
How to Achieve It: Apply pomade to damp hair and blow dry while brushing the front up and back. Use more product to slick the sides close to the head.
Best For: Medium-length straight or wavy hair. Adds height to round face shapes and balances longer faces.
The Rum Runner Ringlets
The Style: Natural or enhanced curls left untamed and chaotic, perhaps with a thin braid or two hidden within.
How to Achieve It: Enhance natural curls with curl-defining cream and scrunch while drying. For straight hair, create curls with a small-barrel iron, then separate and tousle thoroughly.
Best For: Naturally curly or wavy hair, though it can be achieved with styling tools on straight hair. Complements most face shapes, especially oval and heart shapes.
The Navigator’s Top Knot
The Style: Hair pulled into a half-up knot or bun at the crown, with the remainder hanging loose—practical for keeping hair out of eyes while navigating.
How to Achieve It: Gather the top section of hair and twist into a messy knot. Secure with pins and rough up the remaining hair with sea salt spray.
Best For: Medium to long hair with any texture. Creates nice proportions for oval, round, and heart-shaped faces.
The Cutthroat’s Crop
The Style: A short, rugged cut with uneven texturing and a deliberately rough finish, like it was cut with a dull blade.
How to Achieve It: Ask your barber for a textured crop with point cutting to create deliberate unevenness. Style with matte clay applied with fingers for a choppy effect.
Best For: Men with fine to medium straight hair. Works well for all face shapes, particularly softer ones that benefit from added texture.
The Cannon Master’s Cornrows
The Style: Multiple tight braids running back from the forehead, keeping hair secure during battle and cannon operation.
How to Achieve It: Section hair neatly and create traditional cornrows or French braids running back. Add small metal beads or cuffs to the ends.
Best For: Curly, coiled, or textured hair with enough length to braid. Flattering for most face shapes.
The Smuggler’s Side Part
The Style: A deeper side part with the heavier side slicked down and the other side showing more volume—rakish yet with a hint of former respectability.
How to Achieve It: Create a deep side part when hair is wet, apply pomade, and comb the heavier side close to the head. Allow the thinner side to have more texture and volume.
Best For: Short to medium straight or wavy hair. Particularly good for round and square faces.
The Lookout’s Long Layers
The Style: Long, straight hair with minimal layering, often tied back for practical purposes when in the crow’s nest.
How to Achieve It: Grow hair to at least shoulder length and keep layers minimal. Apply a light oil for shine and tie back with a leather cord when needed.
Best For: Straight to slightly wavy hair of medium thickness. Frames oval and heart-shaped faces well.
The Island Chief Twisted Locs
The Style: Thick, rope-like twisted locks adorned with wooden beads, shells, or coins—inspired by Caribbean and Pacific island styles.
How to Achieve It: For temporary wear, create twisted extensions or attach pre-made synthetic locs. Decorate with nautical-themed beads and trinkets.
Best For: Men with thick, textured hair or those willing to use extensions. Works with most face shapes.
The Boatswain’s Buzzcut
The Style: A practical, very short all-over cut with slight length variation on top—perfect for the working pirate responsible for the ship’s maintenance.
How to Achieve It: Ask for a #2 or #3 guard on the sides and slightly longer on top. For Halloween authenticity, consider adding a fake scar or two.
Best For: Any hair type, particularly good for those with thinning hair. Emphasizes facial features and suits oval, diamond, and square faces.
The Treasure Hunter’s Tussle
The Style: Medium-length layers cut to enhance natural wave and movement, giving a windswept, adventurous look.
How to Achieve It: Ask for choppy, textured layers throughout. Apply mousse to damp hair and allow to air dry, occasionally scrunching with hands.
Best For: Wavy or curly hair with medium thickness. Softens angular faces and adds dimension to round shapes.
The Sea Dog’s Silver Streaks
The Style: Natural hair color with temporary gray or white streaks added to indicate age and experience on the high seas.
How to Achieve It: Use temporary hair color spray or chalk in silver or white on small sections, concentrated at the temples and throughout the hair.
Best For: Works with any hairstyle and face shape, adding instant character and age to your pirate persona.
The Captain’s Tricorn Tailored Cut
The Style: A versatile cut specifically shaped to work with a traditional pirate’s tricorn hat—shorter on the sides with controllable length on top.
How to Achieve It: Get a cut that’s shorter around the ears and nape but leaves enough length on top to style either forward or back, depending on hat placement.
Best For: All hair types and most face shapes. Practical for those who plan to wear an authentic pirate hat as part of their costume.
Anchoring Your Look: Maintenance Tips for Pirate Hairstyles
Before you set sail for your Halloween adventures, consider these practical tips for maintaining your buccaneer appearance:
- Embrace authenticity: Historical pirates didn’t have access to modern hair products—a slightly greasy, lived-in look is perfect for authenticity.
- Consider temporary options: For more extreme styles like dreadlocks or color changes, look for clip-ins, temporary sprays, or washable products.
- Coordinate with facial hair: Most pirates sported some form of facial hair—consider how your hairstyle works with a beard, mustache, or sideburns.
- Weather-proof your style: Use strong-hold products if you’ll be outdoors—authentic pirate hair should look like it can withstand sea winds!
- Remember your hat: If your costume includes a tricorn hat or bandana, practice wearing it with your hairstyle before the big night.
- Add authentic accessories: Small braids with beads, coins tied with thread, or even a small (fake) bone can elevate a simple style to true pirate territory.
- Dirty it up: For the most authentic look, consider adding a spray of dry shampoo powder to dull the shine and give hair that unwashed, seafaring appearance.
With these swashbuckling styles and practical tips, you’ll be ready to command respect on the high seas—or at least at your Halloween gathering. Remember, the most fearsome pirates wear their rugged looks with complete confidence, so whatever style you choose, own it like you’ve just seized a merchant vessel full of Spanish gold!
