I believe in balance as it relates to men’s accessories — both in business attire and casual attire.
What applies to men’s clothing also applies to men’s hat styles.
Here’s one example:
If you’re 6’2 and above and your shoe size is 10-½ and above, you shouldn’t be wearing a 1-½” disco cuff or a plain hem on your trousers or suit pants.
That is not balance! You need not exaggerate your already elongated body. (The one exception is a plain hem on formal dress pants — that is perfectly fine.)
Here’s another example:
If you’re 5’8 265 lbs. then plaid is not your friend.
You need not exaggerate your girth!
You should apply those same principles to when choosing mens hats.
The Best Men’s Hat Styles Based On Face Shape
If you have a full face / round head…
You should be wearing one of these hat styles:
A fedora is a felt hat with a soft brim and indented crown. It is typically creased lengthwise down the crown and “pinched” near the front on both sides. Fedoras can also be creased with teardrop crowns, diamond crowns, center dents, and others, and the positioning of pinches can vary. The typical crown height is 4.5 inches. Source
Notable men who often wore a fedora hat:
- Frank Sinatra
- Michael Jackson
- Humphrey Bogart
- Al Capone
- Johnny Depp
#2 – Newsboy 8-panel cap
The newsboy cap or newsy cap is a casual-wear cap similar in style to the flat cap. Sometimes also referred to as the: Baker Boy, Bandit Cap, Apple Cap, Eight Piece Cap, Eight Panel, Cabbie, Jay Gatsby (from The Great Gatsby), Fisherman’s Cap, Pageboy, Applejack Hat, Lundberg Stetson, Chiz Hat, and the Poor Boy Cap. It has the same overall shape and stiff peak in front as a flat cap, but the body of the cap is rounder, fuller, and paneled with a button on top, and often with a button attaching the front to the brim (as the flat cap sometimes has). Source
Notable men who often wore a newsboy hat:
- Brad Pitt
- Paul Newman
- Samuel L. Jackson
#3 – Safari hat
Although similar to the classic Australian outback hat, safari hats are actually fedoras with the brimmed turn down. Often constructed from durable yet slouchy materials like straw, cotton or canvas, the classic safari hat is generally distinguished by its center dent or teardrop crown and 2.5-inch to 3-inch long brim. Source
Notable men who often wore a safari hat:
- Indiana Jones
#4 – Panama straw hat
The Panama hat is one of the more beautiful and timeless styles around. Technically Panama hats come from Ecuador, not Panama, but the widespread use of these hats during the construction of the Panama Canal granted them the name we all use today. Panama hats are not one style. Instead, they are characterized only by their material, Toquila Straw. A panama hat can be made into any shape or style using its distinctive straw and depending on the fineness of the fibers used can be priced up to tens of thousands of dollars. All that said, when people talk about the Panama hat they tend to think of the wide-brimmed plantation or fedora style that is most common. Source
Notable men who often wore a panama straw hat:
- Sean Connery
- Mick Jagger
- Tom Brady
- Prince Charles
Must read: A Guide To Mens Hat Styles
If you have a thin face / narrow head…
You should be wearing one of these hat styles:
The difference between a fedora and a trilby: Traditionally a fedora has a wide brim and a wide ribbon band and bow. A trilby has a narrow brim and narrow ribbon, although there are some American trilbies that still have the wide ribbon. Source
Notable men who often wore a narrow brim fedora hat:
- Bruno Mars
- Colin Farrell
- Ne Yo
- Lebron James
#2 – Pork pie hat
It has a narrower brim than a Fedora and a flat top with a circular indent. Usually the brim is worn up. It is often worn with a goatee, soul patch, and/or toothpick. Source
Notable men who often wore a porkpie hat:
- Rocky Balboa / Sylvester Stallone
- Buster Keaton
- Elvis Costello
- Arsenio Hall
The bowler hat, also known as a bob hat, bombín or derby hat, is a hard felt hat with a rounded crown, created originally during 1849. The bowler, a protective and durable hat style, was popular with the British and American working classes during the remaining 19th century, and later with the middle and upper classes in the United Kingdom and the eastern United States. Source
Notable men who often wore a bowler hat / derby hat:
- Winston Churchill
- Billy the Kid
- Butch Cassidy
- Stan Laurel & Oliver Hardy
- Lou Costello
#4 – Flat cap
A flat cap is a rounded cap with a small stiff brim in front. The hat is also known as a cabbie cap, longshoreman’s cap, cloth cap, scally cap, Wigens cap, ivy cap, derby hat, jeff cap, duffer cap, duckbill cap, driving cap, bicycle cap, Irish cap, Newsboy cap, Crook cap, Joao’s hat, Sixpence, or a Paddy cap. Source
Notable men who often wore a flat cap:
- David Beckham
- Spike Lee
- Matthew McConaughey
- Leonardo DiCaprio
- Justin Timberlake
- Idris Elba
Must read: Newsboy Caps vs Flat Caps
The above examples are simply guidelines to consider when choosing mens hat styles based on your face size and face shape.
If you’re a gentleman who enjoys fashion and wants to throw caution to the wind, then by all means wear whatever makes you feel good!
I’ve been in the men’s clothing business since 1991. My specialty is custom-tailored suits and shirts, as well as men’s accessories.