The Shackles enjoys an ample supply of designs and textiles from all corners of Golarion, lending its ports eclectic fashion. On a vessel, the need for cool, breathable clothing which won't trip up a sailor limits expression somewhat, but freebooters have a need to convey some level of wealth and experience through their style. The following lists garments most common in the Shackles, but any outfit from Avistan to Tian Xia wouldn't be out of place.
Most sailors, even far out at sea, have at least some modesty, so if nothing else they will don legwear. Most popular are knee breeches, a baggy type of pants which extend to just below the knees and may be worn open or tied off. Skirts fill the same role as open breeches but are less popular even among female sailors. Thin trousers are very common, drab or striped, sometimes with leather pockets. Petticoat breeches are a rugged garment which may be worn on their own or over other types of legwear; the name comes from the fact that they are so baggy and voluminous that they resemble a lady's skirt. These types of legwear are unfitted, whereas pantaloons closely hug the leg and are generally ankle-length. Impractical for a typical seaman, they are favoured by captains.
It isn't unusual to see a sailor on deck without footwear of any kind, but most prefer to wear low, simple rounded shoes of cheap black leather, perhaps with a brass buckle. With these, one might wear white knee-high socks or hose, or wear no socks at all. Free Captains have some reputation for wearing tall leather boots with high heels, though these are more appropriate for a cavalier rather than a sailor, and the leather tends to degrade quickly in saltwater.
Freebooters, when they aren't shirtless, prefer baggy full shirts of bleached linen. The extra length is tucked into one's breeches to act as an undergarment. Collars and cuffs, if they haven't been removed, are narrow, and they may be worn unbuttoned and even slashed for additional airflow. Among landswomen of the Shackles, very low-cut blouses which bare the shoulders are in fashion. A captain might have a shirt with a large collar, lace trim, and complex embroidery. It is often practical on cooler days to wear a coarse waistcoat or jerkin over one's shirt, and most freebooters prefer a long, colourful sash around the waist or over the shoulder. Around the neck or collar, some type of kerchief is nearly ubiquitous. Belts and bandoliers tend to be of black or brown leather with small brass buckles.
For watches in inclement weather, a sailor might don a peacoat, also known as a jackanape coat or monkey jacket. In a storm, they may wear a watch coat, which is a very large overcoat sometimes painted with tar to keep it waterproof. A longer peacoat common among naval officers is known as a bridge coat. Common freebooters might wear a frock coat, which is a thin coat worn by servants and workers. A captain might wear a richly trimmed bridge coat, a fine leather frock, a thick Chelish doublet, or a long cape.
Sailors throughout the Inner Sea wear warm knit caps, typically of wool, but seamen working in the hot sun prefer to wear their kerchiefs as bandanas. Round hats with short brims are practical for keeping the sun out of the eyes, and less practical freebooters like to don wide-brimmed hats, especially if they are duelists. These wide-brimmed hats can be pinned up on one or more sides, and if pinned up on three sides can be worn as a tricorne, which is popular among captains. Feathers and pipes are typically worn in the bands of hats. Expensive, voluminous wigs are sometimes worn by pirate captains.
Practically every sailor carries a brass knife, and many carry a small hatchet as well. Freebooters prefer one-handed thrusting or curved swords such as cutlasses, rapiers, scimitars, kukri, and machetes. Firearms, mainly pistols and muskets, are very popular in the Shackles. Heavy armour is never worn - freebooters might wear a secrete, which is a steel skullcap under one's hat, and perhaps an armored coat, but most will go unarmoured. Officers might wear expensive spider-silk bodysuits or mithril chain shirts, or they may equip themselves in the style of the Chelish navy with steel breastplate.
Across Avistan, many cultures believe that piercings and trinkets of precious metals and jewels will pay one's way to the next life. In Garund, it is largely held that material possessions will not be brought with you, but scars and tattoos will give you power. Freebooters, being a highly superstitious lot, subscribe to all philosophies with enthusiasm. They are known to decorate themselves with every type of jewelry and piercing, scars, tattoos, dyes, paints, and exotic trinkets. Their pieces tend to symbolize their values and experiences, or act as fetishes to bring them luck.