The pillbox is an iconic hat style that evolved out of Roman military attire and grew into a fashion item worn as part of an everyday outfit.

Military

The the Roman Empire’s military soldiers wore a pillbox-style hat that’s now seen as a predecessor to the modern version. That design was used through the 19th century as military wear by members of the British Army.

Photography: Flickr

Construction

During the 1930s, a modernized version of the pillbox started to rise in popularity. It was normally crafted from wool, velvet or fur. Rumor has it that this pillbox hat was originally created for actress Greta Garbo.

Photography: Amazon

Beyond The Military

The 1950s ushered in another fashionable era for the pillbox hat as they became part of the flight attendant uniform for airlines. The outfit normally included a pillbox hat, a skirt, a blazer and a collared shirt.

Photography: Flickr

Celebrities

Of all the pop culture figures to wear a pillbox hat, the most notable was United States’ First Lady and 1960s style icon, Jacqueline Kennedy. Famous actresses Doris Day and Audrey Hepburn were also well known for their stylish pillbox hats.

Photography: Wikimedia Commons

The Pink Hat

Kennedy’s hat was the most popular design —it was pink with a matching suit and white gloves. Many of her hats are now archived at the John F. Kennedy Presidential library and museum.

Photography: Wikimedia Commons

Modern Age

These days, pillbox hats are still very much alive in certain fashion circles. You’ll find hats made for black-tie events, with veils for weddings and made in countless colors and fabrics. Some brands have even expanded on the pillbox hat by exploring looks that aren’t round or circular like the originals.

Photography: Etsy