The Dapper Gent’s Guide to Choosing a Hat

Sweet looks for the stylish set.

Wearing a hat speaks of confidence and style. Whether you’re donning a ballcap for the game or a ride with the top down, dressing up with a pork pie or out for a stroll with the missus in your new Panama hat, what’s on your head says a lot for what’s inside it. Many dapper gents gather a collection of hats and knowing which one to choose for which occasion can make all the difference. It’s an honorable mention in the category of celebrity swag that can instantly make you look and feel attractive, though it can be a bit more involved than choosing a new watch.

The Right Size

Start with choosing the right size of your hat. A headpiece that’s too small will make you look like your mother dresses you funny, a too-big hat makes you downright meme-worthy. Visit a local tailor shop (or the place where you buy suits), and ask for a brow measurement for hats. Take three separate measurements. The first should be on the brow where you will most likely wear a hat. Take another a half-inch below for when you pull your hat down to cover your eyes and another for when you raise the brim of your hat (this one located a half-inch to an inch above the eyes). You do raise the brim when you meet someone new, don’t you?

Casey at the Bat

The ballcap is a staple of hat-wearing men the world over. It pairs nicely with a pair of faded jeans and a light jacket. In some places, it’s an essential part of showing team support or proudly displaying pride in one or more accomplishments. In others, it’s a great way to keep heads cool and unburnt when working long hours. Most ballcaps are adjustable, but please make sure that you choose the right fit. Match the hat to your outfit (or vice versa), and don’t wear one if you aren’t outdoors or driving with the top down (possible exception for actual truckers). There’s almost always a better choice when you’re not at the game or other outdoor events, and making the right choice is an important life skill.

Country Folk Will Survive

The blue jeans and t-shirt crowd doesn’t have to give up hats entirely. If you’ve got a pair of leather boots to strap on and a sleek cowboy hat, you’re already ahead of the style game. Remember, white hats for the good guys, black for the bad … unless you’re Nat Love, Rooster Cogburn or Boss Hog. You probably aren’t the one of first, and you don’t want to look like the last. Match the color of your hat to your boots and your belt, and you’ll really be in style. Throw on an unbuttoned plaid shirt over that t-shirt and now it’s a night on the town with the boot-scooting bandwagon.

Fedoras and Pork Pies

Are flat-front or pleated slacks more your style? Did you shudder at the thought of wearing a ballcap anywhere outside of a baseball game? Fedoras may get a bad rap due to the number of men acting poorly while wearing them or donning them inappropriately. Be the exception. Fedoras and pork pies are more than appropriate when you’ve slipped into suit pants or slacks, and they say that you’re a man of style and business. Ties are optional, but you’ll want a sharp collar. Know when to tip your hat, when to lift the brim and when to remove it entirely. If you’ve got a wide face, go with a pork pie. A long face looks best under a fedora. This is your chance to be the ladies’ man you’ve always had inside. Act like it.

Gamblers and Panamas

Do you have a suit of a different color? If you have a leisure suit, and it’s not polyester, get a gambler or Panama hat to match. If it’s a polyester leisure suit, burn it as a tribute to your new self. In this instance, the hat can match the suit and pants instead of the belt and shoes, though those need to complement the overall colors. Gambler’s hats are great for posing for eye-catching selfies at social events with close friends. Panama hats look good at the beach when you’ve got your strolling suit on or at open bars almost anywhere. Just remember to take both hats off when you’re indoors unless you’re actually gambling. Gambler’s hats indoors are for the gambling table, after all.


Three-piece suit and tie? Ready to meet the Queen? A night on the town with the droogies? The bowler is a hat of refinement and sophistication. It requires a suit (or the opposite of a suit, if you’re lampooning the look like a fiend from “A Clockwork Orange” by wearing white suspenders and a codpiece). Real Horrorshow. Bowlers come in many colors, but unless you’re wearing a green suit for St. Patrick’s Day, supporting a cancer drive in pink or secretly Willy Wonka, go for black. Grey and navy blue are also acceptable if they match the suit.

The Right Color

“Hat matches belt and shoes, almost always.” This is a mantra. It also applies to watches. There are exceptions, as noted above, but you can’t go wrong with this pairing. Strangely colored hats are fun, but they’re only attractive when they’re worn as a specific statement. That might just mean “look at me” at a carnival or holiday event, but that emerald green suit and bowler shouldn’t be daily attire unless you’re a leprechaun. Use these tips to determine which hats to wear (and when to wear them), and dress to impress. You never know whose eye you might just turn.

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