Men’s Hats Throughout the Years

As much as people like to say that headwear is a functional accessory, the truth is that it was always a fashion piece first.  As a conscious choice, hats always seem to add a little extra punch to an outfit, even if they are a sort of anachronistic accessory.  Hats have been largely absent from menswear from the 1980s to the 2000s, but if you take a look at recent editions of Pitti Uomo, or even just at your local mall, you’ll see they’re coming back. The fact that they have seen a slight resurgence inspired this article, where I briefly talk about how hats have changed through classic menswear.

Back in the early 1900s, stylish clothing was a privilege reserved for the wealthy. The rich had not only different outfits for different occasions, but different hats as well. Top hats were reserved for white tie, while homburgs and bowlers rounded out the pieces appropriate for suits. In fact, the homburg and derby really reigned supreme until the 1910s. Most hats of this period went for an elegant aesthetic, being stiff and made of fur felt, silk ribbons, and leather sweatbands. Crown shape/height and brim width certainly varied throughout the years, but hats pre-1920s were typically moderate all around. The pinch-front felt hat with the curved, upturned brim was an especially popular model. The straw boater was also quite popular during this period and would remain relatively unchanged in shape until the 1950s, when brims were shortened. Wool caps were a “sporty” alternative, a quality that seems to have stuck with this type of hat ever since. Early caps were pretty utilitarian, made with pleats, belts, and flaps to keep the wearer comfortable, warm, and stylish.

1900s -1930s

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While these wool caps have stood the test of time (currently serving as the “vintage hat of choice” for many), no other hat is as iconic as the soft felt fedora. It was first introduced in the 1890s but didn’t catch on until the 1910s. Like suits, fedoras definitely went through changes with each era as tastes evolved. Early fedoras had a tall crown (mainly with a center crease) and either was upturned or downturned all around; again, varieties were always present. In general, the fedora was certainly a contrast to the narrow-brimmed, stiff homburg of preceding years.

The evolution of the fedora

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By the 1920s and 1930s, the fedora was the hat of choice for almost all men. Homburgs were only reserved for formal men, while the top hat was starting to fade from men’s wardrobes. It probably helped that fashion was finally getting into the hands of the everyday man, who wanted a hat that was stylish and functional at the same time. A high crown fedora was still in vogue for this period, with 2-inch brims and a semi-wide ribbon (narrow ribbons were reserved for casual or western themed hats). One of the main differences between these fedoras and the older ones was the fact that the brim “snapped down” in the front. While boaters were still worn, the panama hat was the smart piece of choice for the warm season, with the optimo model (featuring a center ridge) being the most popular.

Short rounded porkpie hats grew slightly in popularity in the late 1940s with creative types, and at the same time, fedoras got a bit wider. The newly lowered crowns started to have more of a teardrop top and prominent pinch, instead of the simple center crease; eventually, a fully circular top would become fashionable in the 1950s. Straw hats were increasingly popular in the post-war era, with colorful bandana-esque ribbons. Not all of them were designed like the optimo, with most being most similar to fedoras; the actual weave would vary from model to model.

During the ivy movement of the late 1950s and early 1960s, suits became more minimal. Lapels got smaller, darts were lost, and trousers became flat front. In order to match this “slim look”, fedoras went through some changes. Crowns became short and tapered and the brims were heavily reduced. You can see a lot of this style in early Bond films or period productions like Mad Men. Personally, I don’t think this shape is as flattering as the other decades before it.

1940s – 1960s

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Unfortunately, hats (and other formal pieces) were discarded moving forward into the 1960s. As a whole, men were dressing up less and the new ivy/continental look seldom incorporated hats. It didn’t help that cars were getting smaller, so men couldn’t drive while wearing a hat. Soon, headwear became just another fashion accessory that wasn’t needed in the world. By the late 1960s and early 1970s, men wore ball caps, bucket hats (from the recent war), and flat caps if the weather called for it. The fedora did make a brief comeback in the 1970s and the early 2000s, but those two models couldn’t be more different than each other. The disco era one was reminiscent of 1940s ones, though they were often made of wool (rather than felt) and had a wide brim; by contrast, the fedoras of the millennium were clearly modeled after the short, tapered 1960s ones except embroidered cotton was now the fabric of choice.

Today, hats seem to be coming back, worn by stylish men who want to add something extra to their sartorial style. It’s usually for vintage-inspired outfits, but I really do enjoy it. While floppy fedoras (sans ribbon) seem to be the most popular, you can still see western ones frequented by Americana-workwear enthusiasts, as well as beanies, berets, and caps in other circles.

1970s – Modern times

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Personally, as much as I like vintage style, I still can’t bring myself to wear hats too often. However, the fact that more guys seem to rock headwear with their tailoring might change my mind. Perhaps the stigma against the hat within classic menswear can finally go away!

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Ethan Wong
Ethan Wong lives right in the middle: he’s too modern for the vintage scene and yet too vintage for classic menswear. When not at work, he spends his time writing and taking pictures for his blog, Street x Sprezza, which is all about bringing vintage style into the modern day. With a large collection of thrifted vintage and contemporary clothing, he often wonders when his closet will finally implode.


  1. Max Alexander

    March 27, 2018

    The trouble with dress hats today is we no longer have any hat infrastructure. There is no place to put them, in restaurants, on airplanes, anywhere. I bring my handmade premium Montecristi to Europe every year, and I spend most of the flight worried that some douchebag will toss his backpack on top of it. As I am self-employed I fly steerage and do not intend to buy a business-class seat solely for the protection of my hat. But that’s what it has come to.

  2. Matthias

    April 1, 2018

    I second the lack of infrastructure! I love finding places with practical coat and hat hooks, which are increasingly rare as it’s either coat check or throw your stuff in a pile.

    For both style and practical reasons, I hate going out without a hat or a cap and look forward to the day when I’m not in the minority.

  3. Alan

    April 2, 2018

    It’s much easier (and causes less comment) to wear a hat or cap for practical rather than stylistic reasons. So, wear a trilby/fedora with an overcoat or raincoat against the cold and/or wet, or a straw hat in strong sunshine, and it’s entirely justified. “Suit-and-fedora”, however, without the outer coat, looks affected to me. Caps look great with tweed overcoats and simple raincoats of the style Americans call Balmacaan, and also with tweed jackets.

  4. Fábio Venhorst

    May 14, 2018

    Nice article. I do wear hats every day, I have fedoras, homburgs, bowlers and a top hat.

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