Women's hats and bonnets were produced by a specialized worker known as a milliner. The word 'milliner' was first recorded in 1529, when the term referred to the products for which Milan and the north of Italy were well known, i.e. ribbons, gloves and straws. Those who imported these highly popular straws were called "Millaners" from which the word was eventually derived. The products of a milliner represented the labors of many specialists, such as flower makers, feather dyers, straw braid or bonnet makers, felt makers, ribbon and trimming makers, and even embroiderers as well as the manufacturers of lace, linen, cotton, and silk goods.

In the 1770’s, (when huge wigs and hairstyles were fashionable) the ‘calash’ bonnet was worn to protect the high hairstyles from the weather. These collapsible bonnets were made of strips of wood or whalebone sewn into channels of a silk hood. A long ribbon attached to the top front of the hood, held firmly in the hand, allowed the wearer to hold the calash securely, while walking in the wind.

By 1780, the wide, flattened shepherdess hat came into fashion, as the Romantic longing for a simpler life was extolled in poetry and prose. It was a simple hat made of straw or chip. Straw was generally leghorn, an Italian wheat straw. Chip bonnets were actually made from thin strips of shaved wood. Chip was used by hat-makers in a similar way to braided straw, and so was sometimes called “chip straw” or “chip braid”. But it was still actually wood. It could be plaited or woven, just like straw. Once formed into whatever shape was currently fashionable, it could be bleached or colored, then trimmed with silk, lace, velvet, and feathers. Silk bonnets sometimes had chip and wire sewn into the seams, creating a framework to give them shape. Chip braid is generally created from White pine, Lombardy poplar, or English willow. To make chip a young tree is split into sections and planed smooth. A special plane of knife blades is then drawn lengthwise down the boards, scoring long, fine narrow cuts. A smooth plane takes these fine strips off, which then can be woven.

The late 1780's saw women's hats influenced by the tall, felt French Directorate style. These tall, tapering crowned hats were sometimes called a Postilion after the riders who guided a post chaise coach, by riding one of the horses pulling the carriage, who favored them. The best felt was derived from felted beaver fur. Less expensive felt hats might be made of half beaver fur and some other material such as rabbit fur or wool.

From 1795-1810, the simple high-waisted white muslin dresses and helmet like bonnets inspired by ancient Roman and Greek motifs became fashionable. Empire motiffs were inspired by the wall painting and sculpture revealed during excavations of the lost Roman city of Pompeii, in Italy and books printed on the subject. Thomas Hope's 1809 book, Costume of the Ancients, influenced clothing styles, popularizing Roman and Greek designs.

Turbans became popular after Napoleon's 1802 invasion of Egypt. They were meant to appear exotic. Turbans often included silk and expensive metallic embroidery or brooches.

Women's hats were frequently influenced by men's fashions. A version of a jockey cap, with a slightly larger crown, was popular in the Regency period. The hat was generally made of silk, like a jockey's racing silks. Riding hats, with a lower crown than a man's top hat, were also popular. The postilion hat (shown above) would also fall into this women's hats influenced by men's wear category.

A "Poke" bonnet was a hood-shaped hat that tied under the chin, with a small crown at the back and a wide projecting front brim that shaded the face. The word "poke" refers to the fact that there is room at the back for the hair to be poked up inside the bonnet so that the hairdo was completely covered. It became fashionable at the beginning of the 19th century. The size of the poke bonnet increased until, in 1830, a woman’s face could not be seen except from directly in front.