The 1920s mens hats era was one of elegance, confidence, and personality. During the Roaring Twenties, hats weren’t just an accessory — they were a symbol of status and style. Whether a man was heading to work, out for a night on the town, or attending a social event, the right hat completed his look.
From the classic fedora and bowler hat to the charming newsboy cap and boater, the 1920s brought a variety of iconic headwear that continues to influence fashion today. In this complete guide, we’ll explore the history, types, and modern revival of 1920s mens hats, along with styling tips to help you wear these vintage pieces with a modern twist.
The History of 1920s Mens Hats
The 1920s was a period of transformation — socially, culturally, and stylistically. Following World War I, men’s fashion shifted toward more relaxed and expressive designs. Hats became a daily essential for protection, formality, and individuality.
Cultural Influence
- Social Status: A man’s hat often reflected his profession or wealth.
- Hollywood’s Impact: Film stars like Cary Grant and Clark Gable made fedoras and trilbies fashion icons.
- Urbanization: As cities grew, hats became an identity marker for men across social classes.
Fun Fact: Nearly 90% of men in the 1920s wore a hat when outdoors — it was considered improper to be seen without one.
Popular Types of 1920s Mens Hats
Let’s explore the most recognizable hat styles that defined the 1920s gentleman.
1. The Fedora
Perhaps the most famous of all 1920s mens hats, the fedora featured a medium brim, indented crown, and a sleek ribbon band.
- Material: Felt or wool
- Style: Smart and sophisticated
- Worn By: Businessmen, detectives, and fashionable urban men
- Modern Tip: Pair with a tailored suit or trench coat for timeless appeal.
Example: Think of classic 1920s film noir icons — the fedora was their signature look.
2. The Trilby
Often mistaken for the fedora, the trilby had a shorter brim and a sharper crown crease.
- Material: Tweed or straw
- Style: Sleek and modern for its time
- Worn By: Younger, trendier men of the jazz scene
- Modern Tip: Works great with blazers or smart-casual outfits.
3. The Bowler Hat (Derby Hat)
With its rounded crown and short brim, the bowler hat was the definition of refinement.
- Material: Stiff felt
- Style: Formal and traditional
- Worn By: Bankers, professionals, and upper-class gentlemen
- Modern Tip: Perfect for vintage-inspired events or costume parties.
4. The Newsboy Cap
Casual, comfortable, and working-class chic — the newsboy cap (also called a “flat cap” or “baker boy hat”) became an icon of 1920s streetwear.
- Material: Wool or tweed
- Style: Round and soft with a short brim
- Worn By: Workers, newspaper boys, and young men
- Modern Tip: Combine with jeans, suspenders, and boots for a Peaky Blinders-inspired outfit.
Fun Fact: The newsboy cap surged back into popularity thanks to modern TV shows like Peaky Blinders, which glamorized 1920s men’s fashion.
5. The Boater Hat
Perfect for summer, the boater hat featured a flat crown and brim made of stiff straw, often paired with a ribbon band.
- Material: Straw
- Style: Light and preppy
- Worn By: Sailors, vacationers, and stylish young men
- Modern Tip: Ideal for outdoor weddings, cruises, and retro garden parties.
6. The Homburg Hat
A favorite of politicians and well-dressed aristocrats, the Homburg was a formal felt hat with a center dent and upturned brim.
- Material: Stiff felt
- Style: Distinguished and elegant
- Worn By: Business elites and statesmen (famously Winston Churchill)
- Modern Tip: Pair with long overcoats or tuxedos for classic flair.
7. The Panama Hat
While not originally from Panama, this lightweight straw hat became popular during warm-weather months.
- Material: Straw (Toquilla palm)
- Style: Breezy, comfortable, and travel-friendly
- Worn By: Wealthy travelers and resort-goers
- Modern Tip: Perfect for summer or vacation styling.
How to Style 1920s Mens Hats Today
Though nearly a century has passed, 1920s mens hats remain relevant thanks to their timeless silhouettes and ability to elevate modern outfits.
1. Smart-Casual Look
Combine a trilby or fedora with chinos, a fitted shirt, and loafers for a contemporary twist on vintage sophistication.
2. Formal or Business Attire
Opt for a Homburg or bowler hat when wearing suits or long coats. The structured form complements professional settings.
3. Vintage Streetwear
Recreate a Peaky Blinders vibe with a newsboy cap, suspenders, and rolled-up sleeves.
4. Summer Elegance
Match a boater or Panama hat with linen shirts and light trousers for outdoor events.
Style Tip: Confidence is key — the best accessory to any vintage hat is the attitude that comes with it.
Hat Etiquette in the 1920s
Hats in the 1920s weren’t just fashion; they followed social rules.
| Situation | Hat Etiquette Rule |
|---|---|
| Entering Indoors | Always remove your hat |
| Greeting a Lady | Tip your hat politely |
| Dining | Hats off at the table |
| National Anthem | Remove hat and hold it over your chest |
Vintage Manners: These etiquette traditions still influence hat-wearing culture today, especially in formal settings.
Materials & Craftsmanship: Why 1920s Hats Lasted
The secret behind the longevity of 1920s mens hats lies in their construction. Unlike modern mass-produced hats, these were crafted by skilled milliners.
- High-quality felt and wool: Durable yet breathable materials.
- Leather sweatbands: Ensured comfort and structure.
- Hand stitching and blocking: Produced sharp lines and perfect shapes.
- Natural dyes: Offered deep, lasting color without chemical fading.
Pro Insight: Investing in handmade or vintage-inspired hats today provides similar quality and authenticity.
Where to Buy Authentic or Reproduction 1920s Mens Hats
If you’re inspired to own a vintage-style hat, there are plenty of sources:
1. Vintage Stores & Antique Markets
Explore local vintage shops or flea markets for authentic 1920s pieces.
2. Online Vintage Retailers
- Etsy – Great for handmade reproductions.
- Hat Club – Carries modern vintage-inspired designs.
- Village Hat Shop – Offers premium 1920s-style hats.
3. Custom Milliners
Commission a custom piece for accurate size, fit, and fabric based on 1920s designs.
Buying Tip: When shopping vintage, check the lining, material condition, and band quality — true 1920s hats were made to last.
Frequently Asked Questions (FAQs)
Q1. What was the most popular hat in the 1920s?
The fedora dominated men’s fashion, worn by everyone from businessmen to celebrities.
Q2. Did every man wear a hat in the 1920s?
Yes. Hats were an essential part of a man’s attire — leaving home without one was considered improper.
Q3. What materials were 1920s mens hats made from?
Mostly felt, wool, and straw, depending on the season and hat type.
Q4. Can I wear 1920s-style hats with modern outfits?
Absolutely! Pairing vintage hats with contemporary clothing creates a fashionable blend of old and new.
Q5. What size hat should I buy?
Measure your head circumference just above the ears — most hat sizes range from 55–61 cm (S–XL).
Why 1920s Mens Hats Are Making a Comeback
Vintage fashion is cyclical — and the sophistication of 1920s mens hats fits perfectly into today’s retro revival. Shows like Peaky Blinders and The Great Gatsby have reintroduced old-world charm to modern wardrobes.
These hats represent more than nostalgia; they symbolize confidence, craftsmanship, and individuality — values that never go out of style.
Fashion Fact: According to Google Trends, searches for “vintage hats” and “1920s fashion” have surged over 40% in the past three years.
Conclusion: Timeless Style, Modern Appeal
The enduring charm of 1920s mens hats lies in their ability to bridge generations. From fedoras and trilbies to bowler hats and newsboy caps, each style tells a story of elegance, innovation, and character.
Wearing one today isn’t about costume — it’s about confidence. Whether you’re dressing for a formal event, adding flair to casual wear, or simply embracing vintage fashion, these hats remain the ultimate symbol of classic masculinity and taste.