14 Timeless Hats From The Past That Deserve A Comeback
Fashion trends come and go, but some accessories leave a lasting impression that transcends time. Hats, once a staple in everyday wardrobes, have faded from mainstream fashion despite their practical and stylish qualities.
From protecting us from the elements to making bold fashion statements, these 14 historical headpieces deserve another moment in the spotlight for their unique charm and functionality.
1. The Mysterious Cloche
Bell-shaped and snug, the cloche hat defined the flapper era of the 1920s. Women wore these close-fitting caps pulled down almost to their eyebrows, creating an air of mystery and sophistication that perfectly complemented the liberated spirit of the Jazz Age.
Walking through an antique store last summer, I stumbled upon a beaded cloche that transported me straight to a speakeasy.
The hat’s ability to frame the face while making a bold fashion statement explains why modern designers occasionally revive this feminine classic.
2. The Dashing Trilby
Frank Sinatra elevated the narrow-brimmed trilby to mid-20th-century stardom. Worn high on the crown, this fedora variant exudes a playful elegance.
My grandfather’s cherished collection, each paired with a suit for his jazz gigs, showed its versatility for formal and casual settings, adding vintage sophistication to any ensemble.
3. The Regal Top Hat
Nothing screams sophistication quite like the tall, cylindrical top hat that dominated formal menswear throughout the 19th century. Abraham Lincoln famously added several inches to his already impressive height by sporting this statement piece.
I once wore a replica to a costume party and instantly felt ten times more distinguished! The dramatic silhouette transforms any outfit into something extraordinary.
While perhaps too formal for everyday wear, this iconic hat deserves special occasion revivals beyond magicians and steampunk enthusiasts.
4. The Practical Newsboy Cap
With its baggy, eight-panel design, the newsboy cap, once worn by paperboys, blends rugged appeal with timeless style. A purchase during a rainy London trip proved its rain protection and rakish vibe.
Crossing gender lines, this versatile piece pairs effortlessly with jeans or dresses, evoking working-class roots.
5. The Elegant Picture Hat
Wide-brimmed and often adorned with feathers, flowers, or ribbons, the Edwardian picture hat earned its name by framing the wearer’s face like a portrait. Society women of the early 1900s wouldn’t dream of attending a garden party without this statement piece.
The first time I saw “My Fair Lady,” I couldn’t take my eyes off Audrey Hepburn’s magnificent picture hat at the races. These dramatic accessories not only provide excellent sun protection but create an instant air of refinement.
6. The Rugged Cowboy Hat
Born for ranch life, the high-crowned cowboy hat guards against sun and rain, its creases reflecting regional flair. My first one, a Texas childhood milestone, felt like a badge of independence.
Beyond Western ties, its bold silhouette and weather resistance make it a standout for outdoor festivals or casual outings.
7. The Sophisticated Homburg
Formal yet less rigid than the top hat, the Homburg features a center dent running the length of the crown and a curled brim. Winston Churchill and Edward VII made this German-originated hat a symbol of statesmanship and refinement.
The Homburg occupies that perfect middle ground between casual and formal headwear. When my father wore his to my sister’s wedding, several guests mistook him for the ambassador he certainly resembled!
8. The Playful Beret
Soft, round, and flat-crowned, the beret has bounced between military uniform, artistic statement, and fashion accessory throughout its long history. Its Basque origins evolved into a symbol of French culture and revolutionary spirit worldwide.
During my semester abroad in Paris, I couldn’t resist buying a classic black wool version. The beauty of the beret lies in its versatility as it can be worn slouched to one side, pulled forward, or centered on the crown.
Its ability to convey both artistic flair and military precision makes it endlessly adaptable.
9. The Dramatic Pillbox Hat
Jackie Kennedy cemented this small, cylindrical hat with flat crown and straight sides into fashion history. The pillbox sits perched atop the head rather than pulled down, creating a striking architectural silhouette that photographers adored.
Last Halloween, I channeled Jackie O with a pink pillbox, and the transformation was remarkable! Something about its structured minimalism immediately evokes the early 1960s while still feeling timelessly elegant.
10. The Adventurous Pith Helmet
Designed for British soldiers in the tropics, the lightweight pith helmet’s rounded shape and wide brim fend off harsh sun. Finding my grandfather’s sparked childhood adventures.
Despite colonial ties needing care, its sun protection and distinctive look suit gardening or outdoor pursuits with flair.
11. The Glamorous Turban
Hollywood’s Golden Age transformed the traditional wrapped headwear into a symbol of exotic glamour. Stars like Gloria Swanson and Lana Turner wore elaborate silk turbans poolside, creating an aura of mystery and sophistication that ordinary hats couldn’t match.
At a vintage-themed birthday party, my turban-wrapped updo stole the show! The beauty of the turban lies in its adaptability as it can conceal a bad hair day, add height to one’s silhouette, or introduce bold patterns to an otherwise simple outfit.
12. The Practical Boater
With stiff straw and a flat brim, the boater hat evokes late 19th-century leisure, from sailing to barbershop quartets. Trying one at a vintage boat show surprised me with its airy comfort.
Its clean lines and sun protection make it perfect for garden parties or seaside strolls.
13. The Protective Bonnet
Before sunscreen, women relied on bonnets, with extended brims tied under the chin, to shield their skin. The prairie bonnet’s tunnel-like design fascinated me during my niece’s school play.
Modern versions with UV-protective fabrics could blend historical charm with practical sun defense.
14. The Cozy Ushanka
Russian winters demanded serious headgear, and the ushanka delivered with its thick fur (or faux fur) construction and ear flaps that can be tied up or down. This practical hat keeps the entire head and ears thoroughly insulated in below-freezing temperatures.
During a particularly brutal Chicago winter, my ushanka was the envy of everyone waiting at frozen bus stops. What makes this hat special is its adaptability: ear flaps up for style, down for function.
The distinctive silhouette adds instant character to winter ensembles while providing unmatched warmth that modern synthetic hats struggle to achieve.