Mens Hat Styles: How to Find the Right Hat For Your Face Shape

Ever tipped your hat to a stranger? It's not just fabric on your head—it's a nod to who you are. And let’s face it, picking the right designer mens hat styles is like choosing words for a first impression.

Picture this: You're at an open-air jazz festival; what crowns your style? A Panama hat, fedora crown hat or maybe that suave trilby?

Sure, any cap can shield you from the sun but when did we settle for just practicality over panache?

I’ll tell ya—never! Whether you've got an oval mug or a square jawline, there's more than just shade at play here.

Stick around and I'll show you how to top off that look with confidence. We’re about to match hats not only to occasions but also make them sing in harmony with your facial symphony. Ready?

The Occasion 

Before you purchase a hat, have a clear idea of where you will be wearing it and when.  Weather is another consideration so you know what materials you want in your hat . Although many designer men's hats can be worn interchangeably for casual and semi-formal occasions, others are not appropriate for all settings.  Here are the traditional views of which cap is appropriate for the suitable event. 

Casual Mens Hat Styles

These are everyday designer men's hats that you can wear in a laid-back setting where anything goes. You can wear them for most settings. These are perfect for men who want the most bang for his buck.

Panama 

A stylish Panama hat, often light in weight and color, is your best friend in warm weather and a sign that you're ready to have fun. Originating in Ecuador, many in Panama are made by plaiting the leaves of a toquilla palm plant). Because of this, the hat is strong, lightweight, and breathable. 

Bucket 

The bucket hat is back and more stylish than ever. This is an excellent hat for men who want to dress up in casual clothes. The bucket hat looks just like a bucket, which is what its name means. You can dress up or dress down this stylish piece. Most of the time, this depends on the brand of bucket you want to show off. The downward-sloping brim is suitable for people with fair skin who easily burn, and the sturdy construction means you don't need to be delicate with it. 

Boonie 

The Boonie hat, also called a "booney," is a slouch hat. The military used these lids, especially soldiers that served in hot places like the tropics and deserts. The Boonie and the bucket are both made similarly, but this hat has a few extra features. This one's for men who need extra storage. This is because Boonie hats have a web that goes around the crown and sometimes to the brim. 

Visor 

Visitors are becoming popular again now that athleisure and activewear are becoming more popular. The visor is both functional, and the modern designs are stylish. Newer styles are made of a unique man made straw material called Squishee that protects you from the sun. These men's designer straw hats can be fashionably worn off the tennis court.

Baseball 

The all-American hat lasted for a long time because it could be worn with almost anything. This men's hat is probably the most commonly worn because it is easy to wear daily.

Straw 

The straw hat has evolved in the fashion world. Straw men's hats come in various shapes, sizes, and styles. Traditionally known for summer wear because of the excellent sun protection, but are becoming an increasingly popular choice all year. The newer designs are stylish and functional.

Casual/Semi-Formal Mens Hat Styles

These hats have a bit more versatility in wear.  These are great because you can style them for most events and use it as your daily hat. 

Pork Pie

The pork pie hat is an excellent hat for men to add to their list of choices. As a close relative of the fedora, these small, round men's hats have creases along the inside top edge, flat crowns, and brims that curl up slightly. When pork pie hats and suits go together, they are usually part of the smart casual dress code. Imagine a navy blue blazer, a button-down shirt, khaki pants, a pocket square, and a felt pork pie hat, and you're on the right track. 

Tilby

The trilby has a little spot in men's hats, having a low-angled brim and a retro look. It's possibly the most stylish hat for men. You might think that trying to wear a trilby is risky, but it has become one of the most fantastic hats for men and one of the more socially acceptable pieces of headwear. When a trilby is the right size, shape, and fit, it looks pretty good. 

Fedora 

Once upon a time, everyone in business wore a fedora with a suit. But over its long history, the fedora has become more popular with a broader range of people. To find these designer men's hats, look for an indented crown with a crease running lengthwise near the front on both sides and a soft brim at least 2.5 inches wide. The fedora is a popular men's fashion hat because it can be worn in many ways. 

Journalist 

The newsboy hat, which was very popular at the turn of the 20th century, is now worn by both men and women with good taste. A newsboy hat has an angled brim, eight panels, and a button at the top. The cap is practical and stylish for cold weather because it is made of wool and other warm materials. You can dress down in this one. Just pair it with a casual outfit, and you're ready to go. 

Formal Hats

These hats are suitable for formal events such as holidays, weddings, funerals, and the horse races.  It's always good etiquette to ensure you follow the required dress code.

Derby 

Men's derby hats are also known as bowler hats and billycocks. This formal hat is usually stiff-felt and has a short brim and round crown. In the past, both blue-collar workers and wealthy people wore these men's dress hats. The derby hat could never be left out of a list of hats to wear with suits. 

An All-Occasion Mens Hats

This is a versatile hat that can be dressed down or spruced up for more formal events. You can wear this hat anywhere if you match it with the appropriate attire. It's a great hat for those who only want to add one hat to their wardrobe.

Flat Cap 

The flat cap has a round top and a small, stiff brim in front, like a newsboy hat. These hats for men can be made of tweed or other materials. Even though flat caps were worn by working-class people for a long time, younger men are now wearing them on the weekends to look more put-together. Combine it with a tweed jacket, a nice sweater, or even a nice blazer and khakis for a picnic in the country. Or you can do brunch if that's easier. If a man wears a cap with a suit, he should choose a flat cap. 

Hat Styles to Suit Your Face Shape

Choosing the wrong size and style of hat concerning your face shape may negatively exaggerate certain facial features. Instead, you want a perfect fit and form to highlight or minimize certain traits. Don't forget to account for your beard because it changes the appearance of your face shape. For example, a full beard makes a thin face look rounder and fuller. At the same time, a mustache and goatee will elongate and rounder the face. 

These are the best hat styles to compliment your face shape.

Oval 

The length of this face type is generally one and a half times the breadth of the face. The brow is more prominent than the rounded jawline. Often, it's considered to be the ideal face shape.  

Almost any hat will look great on you if you have an oval face. So, use your face shape to your advantage and browse the men's designer hat collection until you find one you like. However, since oval faces can sometimes look long, it's best to avoid hats with tall crowns, like a cowboy hat, which will likely make your face look even longer. 

Round 

The length and breadth are frequently the same, with a rounded jawline and prominent cheeks.  

 It's best to look for hats with sharp, defined angles that will add some contrast to make up for a round face's delicate features. Fedoras are a top pick for you, especially when worn with a slight tilt. Avoid hats with a rounded silhouette and instead consider hats that add height, asymmetry, or angular details. The Mr. Squishee Classic Fedora worn with the back brim flipped up is an excellent choice to add some definition to your face.

Heart-shaped 

This is a relatively common facial shape. It features a pointed chin and is rounded at the top of the face. A prominent forehead and cheekbones distinguish this face type. 

If you have a heart-shaped face, a hat with a small to medium brim that cuts across the forehead is flattering. Men's fedora hats will look best on you. The Tyler from the Eric Javits men's fedora collection will compliment your bone structure. 

Another style of men's designer hats that will balance your facial features is a beret. This is for the soldier, artist, or someone who wants an edgy look. The Guardian Beret Hat perfectly balances out the width of your forehead. Slant the hat to one side to slim your face and draw attention to the eyes. 

Square 

Square faces have the same length and breadth between the nose and forehead and between the nose and chin.

Similar to those with a heart-shaped face, you should look for a hat with more soft curves and edges and less structure to soften the sharp angles of a square face. The Kaden Beret Hat has a bit more fabric on the top, which makes it less of a straight line and more of a curve toward the face. A beret cap is a round, flat-topped hat made from wool, felt, or acrylic. The beret style is an old favorite.

In the same way, something like the Mr. Georgia's Fedora will work because of its circular shape and rounded brim, which hangs just over the edge of the forehead and lets the strong facial features show through. 

Triangle

Triangle-shaped faces, also called pear-shaped, have a broad jawline, smaller cheekbones, and forehead. If you have a triangular-shaped face, you have a wide jawline with a smaller forehead and cheekbones.

A wide-brim fedora, like the Pike, is the best hat for pear-shaped faces. It has a wide enough brim to balance out your jawline. This is a rocker hat with a western style mixed with bluegrass, making this perfect for music festivals. 

Personal Taste 

Your style reveals a lot about you. Because of this, fashion is one of the best ways to express your style. You get to decide what the world sees, and since there are so many ways to mix and match, there are a lot of choices. A well-fitted hat is an often-overlooked accessory that can boost your style. They are beneficial and can give your wardrobe that little bit of style you've desired. 

How Hats Became to Reflect Personal Style

People have worn hats throughout history. They gave good protection from the sun and other harsh elements and were looked at as a symbol of status. Some hats were usually only worn by the wealthy or those in higher social classes. 

As history went on, so did the styles of hats. Even though many people still wore hats for practical reasons, people started to wear hats for their style and not so much according to their social class. Today, people wear hats more for fashion and personal expression. 

Choosing the perfect hat for you comes down to personal taste and what you want your hat to say about you. Most importantly, you should feel confident.

If you need help finding the perfect designer men's hat, contact Eric Javits today, and we will be happy to help you. 

Conclusion

Picking the perfect hat style is a craft. It's about style and occasion, face shape, and personal flair. We dove into designer men’s hat styles to give you the know-how.

Remember this: casual days call for Panama or bucket hats; semi-formals get spiced up with pork pies; formals shine with derbies on top.

Think of your face as a canvas—ovals can sport almost anything while angles define rounder faces. Soft curves suit squares, and triangles rock those wide brims.

Your style? That's all you. Men`s Hats have journeyed from need-based to statement pieces—so make yours count!

So whether it’s sunny festivals or grand ballrooms, let your chosen headwear be bold but true—a reflection of both moment and man.