Vintage fashion continues to captivate style enthusiasts like me, blending nostalgia with timeless elegance. Among vintage accessories, hats are particularly iconic, reflecting the essence of different eras while adding a unique touch to any outfit…and it’s much more likely that a vintage hat will fit you than a vintage dress or shirt (as I’ve found from experience as a modern Viking)!
This guide explores the coolest vintage hats every fashionista should know about, from the Roaring Twenties to the Nifty Nineties. We’ll dive into the history, modern appeal, and styling tips for each of these fun, timeless treasures. Let’s go!
Cool Vintage Hats By Era
The Roaring Twenties - Cloche Hats
Hat Description:
Cloche hats are bell-shaped, closely fitting headwear that became a defining accessory of the 1920s. The name “cloche” comes from the French word for bell, and the hat’s shape reflects this inspiration. Cloche hats were often adorned with ribbons, feathers, or even brooches, making them both versatile and stylish.
History:
The cloche hat was a favorite among flappers, the rebellious young women of the 1920s who challenged societal norms with their bold fashion choices, including shorter skirts and bobbed hair. The cloche perfectly complemented this new, daring look, emphasizing the wearer’s silhouette while maintaining a chic, modern appearance.
Modern Appeal:
Today, cloche hats can be styled with modern outfits to add a retro touch. Pair a cloche hat with a simple dress or a tailored coat for a cool vintage-inspired look that’s perfect for a day out or a special occasion. Cloche hats have made a comeback in recent years, especially in autumn and winter collections, offering both warmth and style.
Personally, the cloche is one of my absolute fave go-tos for any outfit. It’s great for days when you don’t want to style your hair (or your hair WON’T cooperate), but you still need to leave the house looking clean and fashionable.
The Sophisticated Thirties- fedora Hats
Hat Description:
Fedora hats are characterized by their soft brim and indented crown, typically creased lengthwise down the middle and pinched near the front on both sides. While often associated with menswear today, fedoras have been worn by women throughout the decades.
History:
The fedora gained popularity in the 1930s and 1940s, becoming a symbol of both elegance and mystery. This hat style was closely associated with Hollywood stars like Humphrey Bogart, who popularized the fedora in film noir. The fedora’s association with gangsters and detectives further cemented its place in popular culture.
Although originally worn by men, the fedora was also embraced by women, particularly in the 1950s and 60s, as celebrities like Lauren Hutton redefined it as a unisex accessory. Think Ingrid Bergman in Casablanca (1942) where she meets Humphrey Bogart’s character at the airport – the fedora added to her elegant yet understated look, making it a memorable part of her on-screen style. Katherine Hepburn is another Hollywood star who was famous for her “masculine-inspired” wardrobe. She was ahead of her time by wearing slacks in the 1940s, but by adding a fedora, she kept it classy and sassy!
Modern Appeal:
The fedora remains a timeless accessory, suitable for both casual and formal occasions. Modern fashionistas can style a fedora with a leather jacket and jeans for an effortlessly cool look or pair it with a tailored suit or dress for a more polished appearance. Despite changes in fashion over the decades, the fedora has never truly gone out of style, making it a must-have in any cool vintage hat collection!
The Fabulous Forties- Pillbox Hats
Hat Description:
Pillbox hats are small, brimless hats with a flat crown and straight sides. They are typically worn perched on the head, often adorned with veils, bows, or other decorative elements. The pillbox hat is best known for its simplicity and elegance.
History:
Its design was initially introduced by Gilbert Adrian for Greta Garbo in the 1932 film As You Desire Me, and later gained widespread popularity when Halston designed a version for Jackie Kennedy. This little but mighty hat was Jackie Kennedy’s signature hallmark in the early 1960s. The pillbox hat became synonymous with the refined, understated style of these eras, often worn at formal events or religious services.
Did you know that some fashionistas in the 60s started adding a dimple to the top of their pillbox hats after seeing Jackie O’s dimpled hat at her husband’s presidential inauguration? Halston – a hat designer (milliner) who would become famous in the 1970s for clothes – spent hours shaping the hat to be a perfect, simple dome. Unfortunately for Halston, but luckily for fashion history, high winds were blowing at the inauguration, so when Jackie held the hat to her head to keep it safe, it ever so slightly dimpled. Ever since, it’s been fashionable to add a little dimple or dent to a pillbox hat for styling.
Modern Appeal:
Pillbox hats continue to be a popular choice for formal occasions, such as weddings and church services. They add a touch of vintage sophistication to any outfit and are particularly well-suited for those who prefer minimalist, elegant accessories. The pillbox hat’s timeless appeal makes it a versatile addition to any wardrobe – from yours to an English princess’s.
My only complaint about pillbox hats is that they can be hard to style with very short or thin hair. The solution for me? I put on a long, natural-looking wig so I can pin the pillbox hat to keep it from moving.
The Swinging Sixties - Bucket Hats
Hat Description:
Bucket hats have a downward-sloping brim and are usually made from soft, durable fabrics like cotton or denim. Originally designed for outdoor activities like fishing, bucket hats became a fashion statement in the 1960s.
History:
The bucket hat’s transition from functional outdoor wear to a fashion icon happened during the 1960s when it was adopted by the mod subculture. Its casual, laid-back style made it a favorite among the youth, symbolizing a break from the more structured fashions of previous decades. The bucket hat’s resurgence in popularity during the 1990s hip-hop scene solidified its status as a staple of streetwear fashion.
Modern Appeal:
In recent years, bucket hats have made a significant comeback, embraced by designers and streetwear enthusiasts alike. They are often seen in bold colors and patterns, adding a playful, retro touch to casual outfits. Whether you’re attending a music festival or just looking to protect yourself from the sun, the bucket hat is a versatile and stylish choice.
Growing up in the late 80s into late 90s, I remember my first bucket hat – a cotton, light denim hat with a denim flower. My classmates had all kinds of wild patterns on theirs – from marijuana leaves (ooh, so edgy) to large, bold floral patterns. To this day, I credit my first bucket hats for steering me toward cloche hats – the comfort of a bucket hat, with the style and elegance of an earlier era!
The Glamorous Seventies - wide-brimmed Hats
Hat Description:
Wide-brimmed hats are known for their large, dramatic brims that provide both sun protection and a bold fashion statement. These hats are typically made from felt, straw, or wool and are associated with the bohemian and disco styles of the 1970s.
History:
The 1970s were a time of fashion experimentation, and wide-brimmed hats became a symbol of the era’s free-spirited, glamorous style. Worn by fashion icons like Brigitte Bardot, these hats were often paired with flowing dresses and oversized sunglasses, embodying the bohemian chic aesthetic. The wide-brimmed hat was also a popular choice for summer wear, providing both style and practicality
Modern Appeal:
Today, wide-brimmed hats are a favorite for summer outings, beach trips, and music festivals. They add a touch of drama to any outfit and are perfect for creating a bohemian-inspired look. Pair a wide-brimmed hat with a maxi dress or a swimsuit cover-up for an effortlessly chic ensemble.
I usually bring at least 1-2 wide-brimmed hats when I travel on a cruise, as they’re perfect for keeping the sun off my shoulders and neck while on an excursion or at the beach. How do I travel with multiple hats? Easy – I stack them all on top of my head as I go through security!
The Edgy Eighties - NewsBoy Caps & Edwardian Picture Hats
Hat Description:
Newsboy caps, also known as baker boy hats, feature a rounded crown and a small stiff brim. Typically made from wool, tweed, or cotton, these caps were originally associated with working-class men in the early 20th century.
Edwardian picture hats also made a brief comeback as well in the 1980s. The hats are large, wide-brimmed and often adorned with extravagant decorations such as feathers, flowers, ribbons, and tulle. Designed to complement the high-necked, voluminous dresses of the Edwardian era, the hats made a bold statement and framed the face beautifully. The wide brim served not only as a fashion statement but also as a symbol of social status, as it emphasized the wearer’s place in society through its luxurious materials and intricate designs.
History:
The newsboy cap’s resurgence in the 1980s was part of a broader trend of vintage-inspired fashion. It was popularized by celebrities and designers who embraced its rugged, yet stylish look. The cap became a symbol of casual, everyday fashion, often worn with jeans and a jacket for an effortlessly cool appearance.
The picture hat became popular during the Edwardian era (approximately 1901-1910), named after King Edward VII of the United Kingdom. The fashion of the time favored a more feminine, romantic silhouette, and the picture hat played a significant role in achieving this look. These hats were often worn by women of high social standing and were featured in fashion magazines and on the stage, further popularizing them.
With 1980s period tv series like “Anne of Green Gables”, and films like “A Room With a View” and “Out of Africa”, people became nostalgic for the elegance and formality of that long-ago time. This led to a short resurgence in popularity of the Edwardian picture hat – one that caught my fancy growing up in the 80s.
Modern Appeal:
Newsboy caps have continued to be a popular accessory in both men’s and women’s fashion. They can be worn with casual outfits or paired with more formal attire for a vintage-inspired look. The newsboy cap’s versatility and timeless appeal make it a staple in any wardrobe, as I can attest to. My favorite casual hat is a wool tartan Irish newsboy cap – I pair that with any outfit in any weather and I don’t have to worry about styling my hair!
Today, picture hats are often worn at events that call for vintage or formal attire, such as horse races, weddings, and themed parties. They continue to appeal to those who appreciate vintage fashion and the timeless elegance it represents. Modern designers still draw inspiration from Edwardian picture hats, reinterpreting them with contemporary materials and styles, making them a versatile accessory that can add a touch of glamor to any outfit.
I own a couple of these cool vintage picture hats – they are beautiful in photography sessions, especially with long hair (or wigs).
The Nifty Nineties - Berets
Hat Description:
Berets are soft, round caps typically made from wool, felt, or cotton. They are often associated with French culture and historically worn by artists, intellectuals, and fashion enthusiasts.
History:
While berets have been around for centuries (does anyone recall Audrey Hepburn wearing a beret in the 60s?), their popularity peaked in the 1990s when the grunge and alternative fashion scenes embraced them. The beret’s simple, yet stylish design made it a versatile accessory that could be worn in various ways, from slouchy and casual to structured and formal.
In the late 80s to early 90s, I had a red beret. It felt too bold a color at the time, and it was hard to style with my mostly straight hair, so I didn’t rock it like I could today. Once again, confidence is key to pulling off the look of a cool vintage hat!
Modern Appeal:
Berets remain a popular accessory today, often worn with everything from casual outfits to more formal attire. They add a touch of European chic and can be styled in numerous ways, depending on the desired look. Whether you prefer a classic black beret or a bold, colorful version like my now-vintage red beret, this hat is a timeless addition to any fashionista’s collection.
Summary
These cool vintage hats are more than just accessories; they are pieces of history that bring character, elegance, and a touch of nostalgia to any wardrobe. From the rebellious spirit of the 1920s cloche to the sophisticated flair of the 1940s fedora, each hat tells a story of the era from which it originated. Incorporating these timeless pieces into modern fashion not only honors the past but also adds style to today’s often bland outfits.
By understanding the historical context and modern appeal of these hats, you can make informed choices that align with your personal style. Whether you’re attending a formal event, exploring street fashion, or simply looking to stand out, there’s a vintage hat for every occasion. Remember, the key to wearing vintage hats is confidence—wear them proudly, and let your style speak for itself!
