There was a time when a man would never go out in public without a hat – and by “hat,” I mean a real hat, not a baseball cap with a beer logo on it. But dare I say it? Men (not where I live, but in other parts of the country) are once again starting to pay attention to how they look, re-purposing timeless styles, wearing a jacket with a pocket square, and starting a collection of hats.
The term “collection” is key here, and once you start wearing hats, you’ll quickly discover that one is never enough. You’ll start with a basic black Fedora, then get a Panama hat for more casual occasions, and then you’ll binge-watch Mad Men on Netflix and decide you have to have a short-brimmed Trilby because Don Draper looked so good in it.
English guys know their hats, so I asked Patrick Morrison, founder of luxury British accessories brand Furious Goose, his opinion. “In old photographs every man, from the banker to the street urchin, would be wearing a hat,” said Morrison. “Sadly, this is no longer the case, so when you do wear a hat you really make a statement. People are definitely going to notice so make sure your headgear is worth noticing. As a rule of thumb, you get what you pay for. A quality hat will look sharp, make you feel special and most importantly, last. And you don’t need hundreds of hats, perhaps one summer Panama and a Fedora or Trilby for the colder seasons.”
According to Gath D’Silva, head of design at The Jacket Maker, who makes bespoke ready-to-wear leather jackets, “Men’s hats have made a comeback in a big and multi-faceted way, with a particular style of hat for practically every personal style, outfit and mood. Hats to one’s wardrobe is what throw pillows are to a living room sofa. It adds that oomph and style that is a small element having a major impact.”
D’Silva touts the flexibility of the Fedora, saying “A Fedora would be perfect for a dandy style gent, a maverick or creative individual. This hat is THAT versatile. It goes really well with anything from a sports jacket, shirt and trousers combo to a more relaxed style that may involve a Henley tee, vest and denims or chinos.”
While a hat can be part of a more formal outfit, it can be paired with almost anything. “The Trilby and the Driver are the most versatile hats,” said personal fashion consultant Vanessa Valiente. “These can be paired with anything from t-shirt and shorts to a stylish suit and works for night and day. They also flatter most head sizes, whereas a fedora can make a head look too big or too small very easily.”
Have a big head? Still have your seventies hair? Sizing isn’t an issue. Lamood Big Hats has you covered, literally, with an impressive selection of large size hats, including Stetsons, Fedoras, Panamas, boaters and even a top hat. Located in my home state of Indiana, Lamood creates comfortable hats that are stylish and well-crafted, and in larger sizes than you’re likely to find in your local men’s store.
It’s been so many years since hats were a regular part of a man’s wardrobe, that we have forgotten the etiquette involved when we do wear one. D’Silva is probably one of the few men I know who still tips his hat to a lady (and a tip o’ the hat to you Gath, for doing so!), and he says “This also applies as a polite response to a military salute.” He advises that “Hats are to be removed completely when inside a house, building, church, restaurant, etc. Exceptions are lobbies, lanes, elevators, parking lots, alleys, etc., as they are considered public spaces.” He also says it’s important to remember to remove one’s hat when the national anthem is being played, whether indoors or outdoors, and to remove it for a funeral procession.
Valiente adds that “You don’t want to wear a fedora, Panama hat or any larger brim accessory anywhere that will block someone’s view behind you. This means sporting events, the theatre, a conference, a sit-down concert, etc.”
So what kind of hat should I wear?
If you’re not familiar with hats, picking the right one can be a little intimidating. Catherine Bachelier Smith, founder of California-based event, wedding and wardrobe styling business CBS Lifestylist, adds a California perspective to the hat discussion. “Men’s hats are a funny thing,” she says. ‘They are worn all the time but for some reason, it’s a tad different than a baseball cap, then it suddenly becomes intimidating. Here’s how not to get panicked. Texture is cool. Most men wear two pieces, a t-shirt and jeans or a button down and khakis. That’s fine and good if they are well tailored, but if you add another piece, say a hat, it elevates your one-dimensional look to a third dimensional look! Hats allow you to pop off the page and get you noticed. The great thing about hats is that they are easy to add to your ensemble, they make your outfit way more visually interesting, and they protect you from the sun! Huge!”
Those who are unfamiliar with men’s hat styles will refer to any hat with a brim as a Fedora, but this isn’t the case. “Most people get the Trilby and the Fedora confused,” says Patrick Kenger at PIVOT Men’s Image Consulting. “The Fedora is a bit more classic and has a wider brim. The Trilby has a smaller brim and usually sits at the back or side of the head, so it has less actual functionality. I usually go for a Fedora as it’s a more timeless look.”
Bachelier Smith had this to say about Fedoras – “Fedoras are awesome, but stick to a solid. My husband has a black treated denim hat that he wears at night with a suit or just jeans and a v-neck t-shirt. Very chic. I also think a solid black straw fedora is awesome for daytime. It’s similar to a Panama hat but less of a brim.”
Kenger says the Panama hat is similar to the fedora in shape, but is lighter in color and often made from lightweight straw, making it the perfect summer hat.
Pimp your trilby
When I lived in San Francisco I really did wear a flower in my hair from time to time, but more often, I wore one in the band of my hat. It’s been many years since I strolled down Haight Street like that, but Patrick Morrison gave me a great idea.
Morrison offered a great tip for adding a little variety. “Don’t worry about getting bored with your Trilby,” he said. “You can always pimp your millinery by repurposing your collection of designer pocket squares. Roll the silk square into a thin strip and press on a low heat with plenty of steam. Then wrap the design round the hat covering the existing ribbon. This way you can make the same hat look different every time and add a splash of color.”
Dan Blacharski is editor-in-chief of TheVivant.com.