12 Old Hat Styles Due for a Comeback

One thing our ancestors knew how to do well was rock a stylish piece of headwear. From squat caps to towering toppers, history has produced a hat for every occasion. Here are 12 old styles that, with a healthy dose of fashion and confidence, could still look just as fabulous today.

1. THE CLOCHE

The sleek, head-hugging cloche was the perfect companion to the bobbed hairstyle worn by flappers in the 1920s. The hats were typically left plain to emphasize their bell-shaped silhouette, though they also offered a blank canvas for embellishment. The cloche was most popular during the Jazz Age but it’s occasionally incorporated into retro fashion styles today.

2. THE OTTOMAN HEADDRESS

In Ottoman ceremonial costumes, hats played a starring role. The headgear often featured bright colors, feathery ornamentations, and elaborate designs that signified status. The wearer’s class, religion, gender, and clan could all be gleaned from the way the fabric in their headdress was layered.

3. THE BOWLER HAT

The top hat was popular in the 19th century but it wasn’t always the most practical choice for outdoor activities. When looking for a way to protect the heads of horseback riders from branches, brothers Thomas and William Bowler came up with their namesake cap. The bowler hat was sturdy, compact, and appropriate for most any occasion. Though the bowler hat largely fizzled out by the 1980s, the item’s original London manufacturers Lock & Co. still sell thousands each year.

4. THE PILLBOX HAT

Unlike some hats from history, this one was prized for its simplicity. It could be easily identified by its brimless, round shape evoking that of a pillbox. It began gaining steam in the 1930s before reaching peak popularity with First Lady Jackie Kennedy in the 1960s.

5. THE FASCINATOR

Depending on the look you’re going for, a fascinator can be worn as a subtle accent item or a show-stealing statement piece. The hat is defined as an ornamental headpiece that’s secured to the crown using a headband or comb. Once they fit that criteria, fascinators can take the form of flowers, feathers, fabric, or whatever else the wearer can engineer to stay on their head. And though they’re still popular in the U.K., Americans don’t tend to utilize fascinators outside of Derby Day attire.

6. THE TRI-CORNER HAT

In 17th century Europe and America, tri-cornered hats gave men the opportunity to show off their lustrous wigs poking out from beneath the upturned brim. It’s no surprise then that the hat style died out with the powdered wig fad, but that doesn’t mean it isn’t fit for a comeback. Even if wearers don’t have wigs to flaunt, they could take a page from our forefathers’ book and upgrade the hat itself with feathers, brocades, and fabrics.

7. THE DEERSTALKER HAT

If you’ve seen this hat anywhere, it was most likely on the head of someone portraying Sherlock Holmes. The headpiece has been tied to the character since the books were published in the 19th century (it was the illustrations—not the story—that did it, as Sir Arthur Conan Doyle never mentions the cap in the text). It’s peculiar that an urban detective would be wearing a deerstalker hat in the first place, considering they were designed for hunting game and not tracking clues, but the smartly styled hat’s comeback should be … elementary.

8. THE HENNIN

These striking hats were a clear sign of royalty in the medieval era. Reinforced with wire or padding and draped in fine fabric, the cone-shaped hennin is still synonymous with the stereotypical princess today. English hennins were fairly modest in height, but the French version reached up to to three feet and the hat’s Mongolian predecessor towered five to seven feet high.

9. THE NEWSBOY CAP

This hat goes by many names (the big apple, the eight panel, the Gatsby), but its strongest association is with newsboys at the turn of the 20th century. The floppy, brimmed cap wasn’t just popular with the younger working class. It was worn by men across the social ladder and was a common sight on the golf course.

10. THE PEACH BASKET HAT

The origin of this hat name isn’t too hard to figure out: It resembles a bulky, over-turned fruit basket. The peach basket hat first appeared at the start of the 20th century, but it was shunned by many for being an “unpatriotic” display of vanity during the first world war. It was revived in the 1930s and experienced a popularity streak until the 1950s.

11. THE PORK PIE HAT

This hat is known for having a domed crown inside a pinched rim, creating a shape similar to that of a certain savory pastry. The style was originally worn by women in the 19th century and was later embraced by men’s fashion in the early 1900s (thanks in part to Buster Keaton). It’s not as popular as it was in the 1920s but it recently enjoyed a brief return to the spotlight by way of the Heisenberg character on Breaking Bad.

12. THE CARTWHEEL HAT

Out of context, a cartwheel hat could be mistaken for an hor d’oeuvres platter or a tiny landing pad. The hat was worn slightly askew for an eye-catching look and was often crafted from luxurious materials. But after catching on in the 1930s, the broad hats have since fallen out of fashion.