Many men consider the bow tie a wardrobe staple. It’s both an eye-catcher and a statement piece, often serving as the focal point of many looks. As such, bow ties are often paired with formalwear; ...

bow tie cuffilinks

Unleash Your Fashion Sense with Cufflinks: When and How to Wear Them

At Hisdern, we pay attention to detail. The quality of the fabric, the complexity of the pattern and the clever combination of accessories. All of these elements come together to create a sophistic...

Hats Off: How to Avoid Faux Pas with Modern Hat Etiquette

Hisdern Yang June 12, 2025

While hats are no longer an everyday accessory for most gentlemen, many still enjoy wearing them regularly. Some wear them exclusively for special occasions. So what about modern hat etiquette? Do the hat rules we see in old movies and period dramas apply today?

Let's take a look at the history of hats to learn when you should wear a hat (and when you shouldn't), how to style specific hats, and answer your questions about when it's best not to wear a hat.

A Brief History of Hats

We can assume that humans have been wearing hats for basically forever. Initially, hats were worn for warmth and protection. Later, they became a sign of identity and loyalty, such as in sports and the military.

In the context of modern gentlemen, the hats we think of include flat caps, Panama hats, top hats, and fedoras. Of course, there are many other hats that were once popular, such as bowler hats (known as "derbies" in the United States) and straw hats, but here we will focus on those that are still popular today.

Flat Caps

In the 16th century, the British Parliament required boys over the age of six to wear woolen flat caps on holy days.

Since then, a certain style of flat-brimmed hat has become a must-have item in men’s fashion. The simple and versatile design of the hat—a flat, rounded crown with a small, stiff brim—has long been a practical choice for men of all social classes who value tradition, functionality, and style.

How to Style a Flat Hat

Between the flat hat and all its handsome cousins – including the newsboy, ivy, skelly, gatsby, golf, chauffeur and higdon – there’s probably a similarly shaped hat that works for everyone!

The flat hat pairs well with a variety of looks, from casual to more styled, like with a sweater vest or tweed.

Panama Hat

The Panama hat, despite its name, originated in Ecuador. It dates back to the 17th century, but it wasn’t until the 19th century that it became popular among workers on the Panama Canal, earning it international recognition. Over time, the Panama hat became associated with both sophistication and casualness.

Panama Hat Style Guide

Lightweight and breathable, Panama hats have long been a must-have accessory for hot weather, pairing beautifully with fabrics like seersucker, linen, and madras. They are perfect for summer weddings, outdoor events, and casual vacation looks.

Top Hat

Originating in 18th-century England, the top hat is an iconic symbol of formal dress and sophistication.

The top hat’s towering cylindrical shape and stiff structure made it stand out from other headwear of the time, becoming a status symbol revered by the nobility and upper class. It was the standard formal wear for daytime and evening occasions in the 19th century, but as fashion evolved, it gradually faded out of people’s daily life.

Top hat outfitting tips

Today, top hats are reserved for special occasions that require a white tie dress code, such as weddings, horse races, and ceremonies. A white tie look should also be paired with other white accessories, such as a white bow tie, white pocket square, and even white gloves.

The Fedora

Originally worn by women, the fedora was popularized by the heroine in Victorien Sardou's play Fédora. The hat rose in popularity in the 1920s and 1930s, primarily favored by Hollywood male stars, politicians, and gangsters.

Its wide brim and pleated crown combine practicality and fashion, providing protection from the elements while creating a unique look.

A Guide to Wearing a Fedora Hat

Perhaps a more appropriate question is, what can’t you wear with a fedora?

Fedoras and similar hats such as fedoras, homburgs, borsalinos, pork pie hats, and havanas are unisex choices. These hats reflect personal style and taste, can be dressed up or down, and any color is acceptable.

Rules for When to Wear or Not to Wear a Hat

Modern hat etiquette is much more relaxed than in the past, but the rules still exist. Today, hat wearers are expected to respect social norms and display their personal style sensibly and considerately in a variety of settings. Let’s look at some widely accepted etiquette rules and answer some common etiquette questions.

Hat Wearing Dos:

When deciding whether it's appropriate to wear a hat, consider the occasion and location. If in doubt, contact the event organizer or venue to ask if a hat is appropriate. In general, men should feel comfortable wearing hats in the following situations:

Outdoors
Sporting events
Indoor public places, such as post offices, airports, building lobbies, elevators,
hallways
On public transportation
If the organizer has indicated that hats are acceptable

Hat Wearing Don’ts:

Men should remove their hats in many other situations, some of which feel outdated. People who wear hats tend to have their own set of etiquette - usually a blend of social expectations and their parents!

When entering private indoor spaces, such as homes, restaurants, schools, churches
When eating
When the national anthem and the oath of allegiance are played
When the American flag flies, such as in parades
When introducing yourself
When performing indoors