9 Best Trilby Hats for Men in 2021 – Buyer’s Guide & Reviews

best trilby hats

Trilby hats are quite popular with men, particularly among the hipster crowd. Those seeking a vintage, classic style along the lines of Frank Sinatra often seek it out as well.

The name came from George du Maurier, British – French writer, in his late 1800 novel “Trilby.” When it became a play in England, the main actress wore a narrow brimmed hat. Henceforth the hat style became known as the “Trilby hat.”

I’ll explain more about the Trilby hat, its closest relative, and what are the best Trilby hats available in this buyer’s guide, so keep on scrolling!

What Is a Trilby Hat?

Trilbies are a short-brimmed hat that was once considered the rich man’s hat. It is often referred to as the “brown trilby” by the British and was a prominent staple at horse races. You can easily spot one by its lowered and somewhat pinched brim in the front that gradually goes upwards nearing the back. The crown is hollow and creates a teardrop effect.

This hat style gets frequently mispronounced as “tribly” or “triby.” The correct pronunciation is “tril-bee.” For individuals who are not accustomed to wearing hats, this is a fantastic choice with its discrete design, elegant style, modern shape, and small size.

The unique structure of the Trilby hat is the core of its appeal. It achieves a structured look with the lowered visor and adds a subtle hint of modern boldness to your form. If you want to appear more confident, this is the hat to bring your desire into reality.

A Trilby hat is a cool headpiece with impressive transformative properties. It is stylish and beguiling, setting it in a class all its own.

Fedora Hat vs Trilby

Fedora and Trilby hats are cousins that are often mistaken for one another. There is a lot of controversy and confusion surrounding the two. It gets fueled by a lack of understanding regarding the defining characteristics of each style.

Fedora Hat

The Fedora hat got first mentioned during the 19th century. It was popular from its beginnings and remains a classic style still heavily worn today. These hats are easily dressed up or down for casual and formal affairs. They can get found in fur, wool, and straw materials, with the felt Fedora being most popular. Sometimes you can even find raffia Fedoras for those steamy summer days.

A Fedora hat needs to get well constructed with high-quality materials. The crown is typically over 4 in, with a subtle front pinch. The top has a teardrop shape that is indented one or two inches. A classic fedora will have a brim that is two or more inches. Traditional Fedoras always have a snap brim, which means it can get snapped up in the front or back for styling versatility.

Trilby Hat

Trilbies are more casual than the Fedora style, which enables them to get constructed with lower-cost materials like straw, cotton, wool, and raffia. Unlike its relative, the Trilby hat has a fixed stingy brim that does not snap or move. Its most notable feature is the inward angle from the brim toward the crown. Speaking of crowns, a Trilby usually has a much shorter one than a Fedora.

Similar to its cousin, the Trilby hat also has a pinch and center dent with a teardrop shape. Those features are more prominent on a Trilby and sometimes so subtle on a Fedora that they are barely noticeable.

Trilby Fedora Hat Debate

What truly separates the two hat styles are how they are worn. That is also a source of confusion and controversy among hat aficionados. Fedoras are more versatile in that they can get paired with everyday attire or more formal stylings. Trilbies are generally casual wear only. Both have a great look that is distinctly their own.

What to Look for When Buying a Trilby Hat

Now that we have laid the Trilby Fedora hat debate to rest, here are some tips to help you shop for the best Trilby hat for your style.

Crown Shape

The Trilby hat is pointier with more significantly defined features like the pinching and teardrop indentation. The height is typically very short, with its Fedora relative being much taller.

Brim Size

The short brim is the defining feature of a Trilby hat. With the stingiest of stingy brims, the Trilby hat is the Grinch of the hat world.

How to Wear a Trilby Hat

A Trilby hat is typically worn for fashion and not function. They get frequently worn like a halo on the back of the head instead of level above the eyebrows. The short brim gives the illusion that it is too small when, in fact, that is just the style. 

Choosing to wear this style of hat will cause you to stand out in a crowd. It will dramatically change your silhouette more than any other article of clothing or accessory. People will get drawn to look at you in this hat. That is what a proper hat does, get attention.

Embrace the youthful vibe of the Trilby hat by pairing it with modern designs and current styles. For a smart-casual style, combine a fitted shirt, slim trousers, loafers, and a Trilby. In the summer, grab a light-colored raffia or straw Trilby. When winter sets in, go for a wool Trilby in a dark or jewel tone.

Comparison Table

Product

Material

Brim

Price

belfry straw trilby hat

Material: Straw

Straw

Brim: 1 1/2”

1 1/2”

9 Best Trilby Hats for Men in 2021 – Buyer's Guide & Reviews 1

Material: Wool blend

Wool blend

Brim: 1 3/4”

1 3/4”

Bailey of Hollywood Tino Wool Felt Trilby Hat

Material: Wool Litefelt

Wool Litefelt

Brim: 1 3/4”

1 3/4”

Stetson Radcliff Leather Trilby Hat

Material: Leather

Leather

Brim: 1 5/8”

1 5/8”

Lipodo Smooth Trilby Leather Hat

Material: Leather

Leather

Brim: 1 7/8”

1 7/8”

stetson reidton toyo trilby straw hat

Material: Leather

Leather

Brim: 1 7/8”

1 7/8”

Borsalino Finissimo Fur Felt Trilby

Material: Fur felt

Fur felt

Brim: 2”

2”

Ultrafino Wool Felt Trilby

Material: Wool felt

Wool felt

Brim: 2”

2”

Mayser Classico Trilby Hat

Material: Wool felt

Wool felt

Brim: 2”

2”

The 9 Best Trilby Hats for Men of 2021

1. Belfry Straw Trilby Hat

FEATURES

  • Straw hat
  • Flexible
  • Versatile brim
  • Multi-tonal Toyo straw
  • Unlined
  • Multiple color options

Here is a Cuban-inspired straw Trilby hat with versatility and a timeless silhouette. The neutral color and multi-tonal weave of the Toyo straw is a fashionable choice for the summer months. The short brim can get styled up or down depending on your mood. If you are a guy with larger head size, you are in luck! Hats in the Belfry offers sizes from small through XXL.

PROS

CONS

2. Kangol Wool Player Hat

FEATURES

  • Wool blend
  • Hand wash only
  • Unlined
  • Elasticized sweatband
  • Available in four colors

Kangol has become an easily recognizable staple in the hat industry. Its iconic styles can get seen atop the heads of many celebrities and Hollywood stars.

With a clean look, stingy brim, and seamless construction, it is a popular Trilby shape. The brim can get adjusted to fit your style by flipping it up like a Fedora, down, or a little bit of both like a traditional Trilby.

PROS

CONS

3. Bailey of Hollywood Tino Wool Felt Trilby Hat

FEATURES

  • 100% Wool Litefelt
  • Crushable
  • Water-resistant
  • Removable feather
  • Comfortable sweatband

Bailey of Hollywood has constructed this special Trilby with its famous Litefelt process. The revolutionary system uses a premium felt hat made with natural unstiffened wool and makes the shape retentive and the entire hat water repellent. That is one of the best selling features for this Trilby option. It is strong and nearly indestructible.

No doubt Bailey has brought us one of the best Trilby hats for men. It is a best-seller every year for a good reason!

PROS

CONS

4. Stetson Radcliff Leather Trilby Hat

FEATURES

  • 100% leather
  • Waterproof
  • 100% cotton lining

Stetson has been making high-quality hats since 1865. It is rich in history and full of the American spirit. Stetson is a timeless brand that never fails to bring you a hat made of premium materials, high-quality construction, and beautiful design.

PROS

CONS

5. Lipodo Smooth Trilby Leather Hat

FEATURES

  • 100% pigskin leather
  • Leather trim
  • Heavy materials

It won’t take long to win you over with this all-leather Trilby hat from Lipodo. It has the perfect materials and style to take your look to the next level. The pigskin leather is smooth and sturdy with a rustic yet classically elegant appearance. The leather trim blends seamlessly with the rest of the hat for a polished finish.

The Lipodo leather Trilby will quickly become the number one hat in your collection. The hat size for this runs large, so I recommend ordering a size down.

PROS

CONS

6. Stetson Reidton Toyo Trilby Straw Hat

FEATURES

  • 100% Toyo straw (viscose)
  • Lightweight hat
  • Stetson quality

Keep your sophisticated cool style going during the summer with this elegant straw hat from Stetson. Woven with Toyo straw for a lightweight and smooth appearance, this men’s Trilby hat brings a hip look to a retro style. Elevate your warm-weather ensembles with modern class.

PROS

CONS

7. Borsalino Finissimo Fur Felt Trilby

FEATURES

  • 100% animal hair
  • Made in Italy
  • Grosgrain band
  • Stingy brim

Borsalino uses unique materials in this narrow brimmed Trilby hat. It gets constructed with the finest hare fur felt to provide your head with warmth throughout the winter. It features the traditional crown dent and a grosgrain ribbon trim around the hat that ends with a bow. Golden brand lettering accent this charming felt Trilby.

PROS

CONS

8. Ultrafino Wool Felt Trilby

FEATURES

  • 100% Genuine wool 
  • 2″ Snap brim
  • Traditional dents
  • Water-resistant

While a wool Fedora has a wide, flat brim, this Trilby boasts a short snap brim. That means the brim has been snapped down in the front and raises as it goes towards the back. This sturdy Trilby can withstand moderate crushing and is water-resistant to light rainfall.

With the classic pinch and teardrop crown, this well-loved Trilby style will look great on you. This design could get dressed up for social occasions as well.

PROS

CONS

9. Mayser Classico Trilby Hat

FEATURES

  • 100% Wool felt
  • Grosgrain band
  • Handmade
  • Soft and dirt repellant
  • Corded lining band

Mayser brings a handsome Trilby made with exceptional quality. It is a soft hat that is temperature regulating and dirt repellent thanks to the wool felt. It is a light headpiece that features the classic teardrop crown and a ribbon hatband to complete the look of any stylish outfit.

PROS

CONS

Frequently Asked Questions

Are Trilby Hats Fashionable?

Hats in general are a fashionable way to complete any outfit. Not every hat is going to A Trilby has a stylish brim and sophisticated appearance that cannot get passed up. It is a sleek and smart head covering with a vintage style that has been around for many years, and rightfully so.

Women have also hopped on the Trilby hat train. Many opt for different fabric or material than some of the men’s products, wearing more street and dress fashion hats. A Trilby is just as fashionable for women as it is for men.

If you are looking to bring your sexy back, get the Trilby! give you a great look though. That’s why you want a Trilby.

How Should a Trilby Hat Fit?

A Trilby, like any hat, should fit snug to the head, but not so tight that it leaves marks on your skin or feels tight. If you can place a single finger between your head and the hat, it is the right fit.

Trilbies can get worn about a finger’s width above the eyebrows and ears. However, it is more common and fashionable for men to wear a Trilby on the back of the head, similar to a halo.

Is a Trilby a Type of Fedora?

Actually, yes. A Trilby gets classified as a type of Fedora. Many manufacturers will advertise the Trilby as a Trilby Fedora. Some people also refer to a Trilby hat as a short-brimmed Fedora, although Trilby is the correct term.

Regardless of the hat style, the crucial thing you must do is choose a brim that is proportionate to your shoulders. Choosing the wrong hat for your body can ruin the most banging outfits and take you from sleek to geek in a matter of seconds.

What's the Difference Between a Trilby and a Pork Pie Hat?

Well, you can’t eat a Trilby (but post pics if you try!). It is the crown, of course. The pork pie hat has a distinctive round but flat crown with a crease. Trilbies have a pinch in the front with a tapered crown. A pork pie is a casual hat, while the Trilby is a step above it but still below a Fedora.

Final Thoughts!

You can see the Trilby hat atop heads in many places, if you aren’t in lockdown that is. They can come in a variety of vintage styles with traditional materials as well as modern designs with a wide array of construction options. A Trilby is not worn the same way a typical hat is worn, making it a unique headpiece that easily draws attention to the wearer.

Throughout the last century, Trilbies are seen on the heads of many characters like Inspector Clouseau and Inspector Gadget (now, if we could just convert Sherlock Holmes from a Trapper to Trilby….).

Whatever your fashion style is, there is a Trilby out there for you. Take a chance and add one to your snazzy wardrobe collection today!


Christi Lee

Christi Lee

Christi Lee has been a freelance writer for the past 27 years. She began her career writing for numerous organizations, churches, and charities as a volunteer. Christi has a passion for fashion and loves to write about the latest trends, designs and brands on the market today. She currently lives in the midwest with her six children and an incredibly sweet Guinea pig. If you would like to learn more about Christi, you can visit her website here.

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