man laughing wearing a formal vest and dress hat

A Visual Guide to Men’s Dress Hats The 10 caps that will instantly make a statement

When looking for some protection from the weather, one of the first things most of us reach for is a hat.

Whether it’s a baseball cap for summer or a knitted beanie in the colder months, your casual staples may seem like enough.

However, there’s a whole world of men’s accessories that have taken the back seat in recent decades.

Whether you have an affinity for vintage style or just want to stand out, adding a dress hat to your ensemble is a seamless way to make a statement.

Not sure what’s out there? Check out our guide to learn more.

The Bowler

Black Bowler Hat

Thomas and William Bowler invented the bowler hat in London in the late 19th century.


Kangaroo Black Derby Hat

Bowler Hat Fits Older Kids

Kangaroo Black Derby Hat

A Classic derby hat that fits to adults and children

Also known as a men’s derby hat in the United States, Charlie Chaplin made it famous

Today the bowler hat will add an eccentric touch to your formal get-up.

We recommend choosing a different hat if you have a rounder face, as this silhouette is more flattering when paired with an angular jaw.

The Flat Cap 

Mens Flat Cap
Flatcap2 1

The Flat Cap is known by more names than we care to count — some of the most common alternatives being the ivy cap, cabbie cap, or driving cap.


2Pack Adjustable Newsboy Hats for Men
Flat Cap Mens Irish Cabbie Gatsby Tweed Ivy

Flat Cap for Men

Flat Cap

Anyone looking for a classic style with a twist of modern refinement will fall in love with the flat cap.

This style is categorized by a rounded cap that sits close to the head and the short, stiff brim.

It’s usually made from cold-weather fabrics such as wool, tweed, and cotton.

This style is a step up from the baseball hat but can still be worn with your casual wardrobe.

We suggest you choose a fabric that’s different from your overcoat —matching isn’t always a good thing.

For an updated look, go for the same shape in a suede or herringbone fabric. This little change goes a long way.

The Ascot

Plaid Ascot Mens Hat

The ascot cap looks like a cousin to the flat cap. However, instead of being made from a soft material that sits closer to the head, the ascot is made from a hard round felt material.


Belfry Ascot Molded Wool Ivy Cap
Black Grey Navy Pecan

This classic ascot cap


The sturdy construction of this ascot ensures that it’ll always look good.

Men with hats, This style looks good with both casual and more formal attire.

If you’re wearing a suit in an unconventional fabric or like tweed or plaid, consider adding an ascot for a vintage touch.

The Fedora

Black Fedora

The fedora is probably the best-known hat on this list, but not always for the right reasons.


Men’s Classic Manhattan Structured
Trilby Fedora Hat for Women

This fedora trilby is a classic hat


Perfect classy looking hat that’s practical for keeping your head warm & for looking extra stylish.

A fedora is a brimmed hat with an indented crown. The biggest variations in this style come from the fabric it’s made from and the size of the brim.  

A particularly polarizing style, the fedora is notoriously difficult to pull off.

For an updated look that’s more fashion-forward than dad on vacation, we recommend a felt or wool style paired with a lightweight scarf 

If you’re serious about looking good in one of these, go to a hatmaker and get sized.

Like with most articles of clothing, you can’t go wrong with quality materials and good fit.

The Boater

Boater Hat with Red and Black Ribbon
Boater Hat2

The boater hat is a summer style characterized by its straw weave and wide, round brim.


Boater Hats for Men Women Straw Skimmer Hat
Wide Brim Halloween Christmas Costume

This Truly Iconic Boater Hat


The Boater Hat Fit Most People Head Well.

It has Ivy-Leaguer connotations and is most recognizable as the style worn by barbershop quartets. Today they’re still worn at major boating or horse races. 

More recently it has become popular as a way to dress down a more formal look in the summer months.

Pairing it with a knit tie to achieve a pulled-together look. However tread lightly — with its wide brim, this hat certainly makes a bold statement.

The Trilby

Trilby Mens Hat in Black
Trilby1 1

This hat is similar in shape and make to the fedora, but is characterized by a narrower brim and shorter crown design.


Classic Trilby Short Brim 100% Cotton Twill
Fedora Hat with Band

The classic fedora hats for men


classic men’s fashion gem with the classic fedora hats for men.

The 1960s style was popular as a driving hat when men were looking for something with a shallower top to deal with the shorter ceilings of American vehicles.

This style hasn’t seen much of a resurgence — most people favor the fedora.

However, if you have a smaller face, this hat could be right for you. It won’t overpower your features with its shorter brim. 

The Pork Pie

Gray Pork Pie Hat by Kangol

The pork pie hat has gone through several revamps to get to the style that’s worn today.


The Hat Depot Unisex Light Weight Classic
Soft Cool Mesh Pork Pie hat

Light Weight Classic Soft Pork Pie Hat

Pork Pie

Lightweight Breathable Material is Perfect for any occasions to add on any outfit.

Made of both straw and felt, this hat has a shorter round crown, narrow brim, and associations with the jazz and blues culture.

This hat is easy to pull off and worn year-round — opt for felt in the winter months and straw when it’s warmer out.

This style doesn’t have to look dated if you pair it with updated classics and a pocket square.

The Panama

White Panama Hat with Black Ribbon
Panama2 1

The Panama hat is a wide-brimmed, straw style. It’s sometimes worn with a ribbon around the crown and has roots in South America.


Livingston Fashionable Wide Brim Straw
Panama Hat for Men & Women

Panama Hat for Men


Foldable design makes it easy to store & carry for travels

Try out this style in the summer months. They look great when they’re paired with light-colored or linen suits or other summer styles.

The Homburg

Homburg Hat with Feather

The homburg is a formal hat with a tall, indented crown and wide brim. Less recognizable than the top hat, the Homburg was worn throughout the 20th century but has seen a dip in popularity in recent years.


Levine Hats 9th Street Charles Firm Felt
Homburg Godfather Hat 100% Wool

Bowler Hat Fits Older Kids


High quality, 100% wool homburg hat with deep curl bound brim and grosgrain ribbon bow band trim.

The larger proportions of the hat lends itself well to bold statement, but this isn’t a style you’ll see too often.

The Top Hat

Men's Black Top Hat

If you’ve ever played Monopoly, you’re familiar with the top hat. This classic dress hat is categorized by its tall, flat crown and wide brim.


GEMVIE Men 100% Wool Mad Hatter
Satin Lined Black Low Top Hats

Traditional Black Top Hat

Top Hat

A Classic design with belt will make you so fashion

You’ve probably seen it worn by historical figures from Abraham Lincoln to Winston Churchill.

This may be the dressiest of the hats listed here and today they are a touch too formal for most events. Unless you’re going to a royal wedding, we suggest leaving this style to the board game.

Top it Off

Pitti Peacocks By Beforeeesunrise

Rocking a dress hat may seem like a lofty style goal. But, if you do it with confidence, you’ll be getting those double-takes for the right reasons.

Ease into it with an easy-to-wear hat like the trilby or flat cap. Once you’re comfortable with those, the bolder styles won’t seem so daunting.

You May Also Like