How to choose a Fedora that suits you

Fedoras will always get a bad rap, despite being a fully functional and stylish accessory. It’s probably due to the infamous status of “vintage hat”, gracing the heads of Golden Era illustrations, period films, and your latest Gatsby party (it should be noted that the story takes place in the early 1920s, and the fedora hat reached the peak in popularity in the mid-to-late 20s). The stigma is hard to shake, and I’ll even admit that a fedora hat is one of the few things I can’t really bring myself to wear often, despite being a vintage enthusiast. But that’s changed in recent history.

In my free time, I’ve hung out and shot with Cody Wellema, a hatmaker the California suburb of Pasadena. He is completely self-taught and has gone from fulfilling orders in his apartment to opening up a storefront in a building that has existed since the 1920s. Our friendship led him to develop more of an appreciation for classic menswear, while he has shown me a different side to fedoras. When looking at the old pictures of Jimmy Stewart or even candid pictures of regular Golden Era people, he noted that these people wore their clothes (and hats) naturally. They weren’t trying to put on a certain look, as some guys do today. Wearing a fedora at the time was the same as wearing a bucket hat or a beanie today; you sport it with a suit on a hot day or with a chambray shirt when working. Back in the day, there wasn’t a concern about being dapper.

Black felt Wellema. Works well with minimal outfits.

A couple of guys follow this same mantra. The guys at Bryceland’s are one great example. As I’ve noted before, they have a vintage-meets-modern sartorial/workwear style where the fedora comes in perfectly. Both their personal hats and RTW stock are made by Wellema, which you can see them wear across their social media. They really wear them with everything, from tailoring to rayon shirts to 1950’s pin-up print tees. It might be a bit too bold for some, but it’s definitely miles ahead of any gangster cosplay. Seeing them do it well, in addition to my many conversations and pictures with Cody, really inspired me to get some made for myself. I currently own two Wellemas, a dressy grey and my own take on the brown fedora; they have seen more wear in recent history.  

Yet Bryceland’s isn’t the only ones who wear it. You can see a bunch of people do it during the F/W Pitti. Drake’s featured a floppy brimmed one a few seasons ago. Like pleats, established gentlemen continue to wear it while the like-minded younger generation is seeing the appeal. At no point does it look like a costume or something affected. With the tucked tie before it, it simply takes confidence in your look. But even before that, it takes careful consideration to find the one that suits you.

Like with shoulder styles, lapel width, and jacket length, you need to pay attention to your proportions.

Fedoras vary widely in terms of crown height/shape and brim width, with some combined details bringing specific eras to mind. You don’t always have to play to your facial structure, but at least be conscious of the look you’re projecting. Once the shape of your hat has been determined, you should also decide on the ribbon width: wider ribbons with a bow are more formal whereas thin ones are more “western” and casual. The same can be said for brim treatment; a snap front and upturned back are more traditional and having it up all around is more dressed down.

Color is personal preference, but you really can’t go wrong with a grey or brown, with the latter as my personal favorite despite the ever-present imagined Indiana Jones archetype. Contrasting your hat with your outfit is definitely needed, as to not appear matchy-matchy. A grey fedora works well with a brown suit or navy suit, while brown works especially well with grey or green. For me, I think that grey becomes a bit too formal; brown tends to work better with denim as well as a flannel suit. I’ve also seen the tan/silverbelly one grow increasingly popular since it subverts a lot of people’s expectations over the fedora. You’ll see that in the album I’ll include below.

Lastly, it just stands to say that fedoras are more of a fall/winter item. Due to the “structure”, it creates for your head, it really works best with a fuller cut suit. I don’t mean that you have to wear a 1940’s draped suit, but keep in mind that a close hugging jacket and skinny pants won’t cut it. The idea is to be relaxed in your clothing. Adding coats, sweaters, and scarves also help add to this proportion building, as to not make your head/hat appear too wide.  


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Here are a couple of places that I think have some great fedoras other than getting a vintage one from eBay or vintage store.  

Wellema Hat Co. 

Cody Wellema makes each hat by hand, making him one of the few bespoke hatmakers in the US. He doesn’t have a house style, which means that you can ask him to do anything you want, whether it’s something period authentic or original. He is a wealth of knowledge and a perfect gentleman, who is dedicated to making the hat you want thanks to his enormous collection of hat blocks and vintage ribbons. It is a bespoke service, so it works best if you go in person to get measured (with late 1800s equipment) and consult on the details. He’s done things as crazy as burn distressing to indigo dyed felt! The lead time is a 6-8 weeks since they are done by hand, but it’s completely worth it to have a hat that’s entirely custom and made with the highest quality.

The Armoury 

The Armoury fedora is similar to the Stoffa one, in that the crown is unblocked, allowing it to be styled to its owner’s preference. The brim is 3”, which is a bit too much for my taste (I prefer a sub 2.5” at most), but that just means it looks especially rakish and is sure to protect you from the elements.  The ribbon is thin, which makes it easy to wear casually.

Borsalino / Stetson

I would be remiss if I didn’t mention Borsalino and Stetson, who are perhaps the biggest brand name hatmakers in the world.  I will admit that I have no real experience with these apart from true vintage models (which even then were some of the highest quality on the market), but I’m sure that there are many out there who are pleased with their modern hats.  The Borsalino Traveller and the Stratoliner are probably my picks of the bunch, though the colors available aren’t the most versatile. I’d also suggest leaving the feather at home.



The Stoffa hats are like a combination of a fedora and the original panama hats: they can actually be rolled up! The brand is all about making things more accessible and natural, so these soft felt fedoras lack a ribbon in order to help them float the line between casual and formal. The felt is extremely pliable, so you can style the brim and crown anyway you like. It’s a great one for guys unsure of wearing the traditional fedora, but still want to don one.

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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!