Vintage Black Pillbox Hat

The right vintage or designer hat can transform a look. This humble accessory is your reliable pièce de résistance, boosting confidence and lending an air of sophistication to any ensemble.

Functional and a widely renowned, versatile finishing touch when heading out for a night on the town, hats have long been a part of the history of fashion. Wealthy Egyptians, for example, wore hats to keep them cool in the blazing sun.

In the early 1800s, the wide-brimmed bonnets that women wore became increasingly elaborate. The brims broadened and many were embellished with colorful floral decorations. Legendary fashion designer Gabrielle “Coco” Chanel’s career began in millinery, a term that stems from Milan, Italy, as it was the city best known for producing quality hats during the 16th century. That was before she would set the fashion world alight with comfortable and practical jackets and skirts, encouraging women to leave extravagant clothes behind. Halston, who defined the spare, body-conscious style of the so-called Studio 54 era, was the hat designer for Bergdorf Goodman when he first moved to New York City. He had his first encounter with fame in 1961 when Jackie Kennedy wore a pillbox hat he designed.

From fascinators at a prestigious derby to a baseball cap for a walk in the park, there’s a hat for every occasion. When shopping for the right hat, you’ll want to pick one you feel confident in. Think about size too — you don’t want a wide-brimmed headpiece that will hog the spotlight on every occasion (or maybe you do). If you’ve got a petite face, an oversize hat might be too overbearing.

On 1stDibs find an expansive assortment of vintage and designer hats today. You can search for hats by style, designer or color.