My Custom 1930’s Style Fedora


 Thanks to neckbeards and the internets, fedoras have probably been ruined for everyone.  It doesn’t matter if its actually a fedora (not a trilby); you will be ridiculed for wearing one.  However, all of the stigma in the world didn’t stop me from getting one custom made.

Even though this is a technically a review, I paid for this fedora myself.  This is not a sponsored post.  

Fedoras today can be seen in four places: Gatsby parties (fedoras caught in in the late 20s, making them inaccurate for a roaring 20s event), films, Pitti Uomo, and true vintage events.  They are obviously anachronistic, since men seldom wear hats apart from caps.  It was this very reason that I only wore my fedoras with my true Golden Era vintage clothing instead of more modern pieces (anything after 1960).  Even though Spencer wears more “true vintage” than I do, we keep our use of it to special events like hanging out with Benny or Dapper Day.




I don’t deny that a fedora can look cool.  In fact, tailors like Angel Ramos and Dan Trepanier can definitely pull it off.  However these guys have a decidedly more contemporary style and wear their hats in the same way.  Spencer and I have the bolder choice of going straight 30s/40s (or very close) and that makes it more of a challenge to wear everyday.  I find myself taking off my fedora whenever I have it with me, even if I’m in full vintage (I bring it as a commitment to the look) or at an event.  It also didn’t help that I have a large head (7 3/8, wide sides) which makes it hard to find headwear to begin with.  As a result, I would simply buy fedoras that fit my head with the least resistance.  All the fedoras you saw on my lid were stretched out as far as they could and even then they were a hassle to put on.  Perhaps the reason I didn’t wear my fedoras often was because I haven’t found one that fit!  Coming to that conclusion, I decided to look around for a custom hat maker.

Now a good modern fedora can cost anywhere from $200-$800 depending on the manufacturer (Stetson and Lock & Co come highly recommended) or the seller (J.J’s Hat Center), but a majority of the price comes from the fabric.  Fur-Felt is the main way to go, since wool-felt is lower quality and can be cheap; the latter also is prone to shrinking.   Fur-Felt then comes down to the type of fur, with beaver being the premium fabric (and most expensive) and rabbit being the most common.  Texture of these felts can come to play, whether you want smooth, soft, or “hairy”.

When looking around for a hatter, I decided to visit Joyride:  Vintage for Men, one of my favorite vintage stores in Southern California.   In recent years, they have been able to expand their hat repair and cleaning station into a full-blown custom hat shop, using real vintage hat blocks.    They did great work on cleaning my vintage fedoras and even stretched a lot of them to the hats’ limit because of my big head.  Joyride agreed that getting a custom fedora was the best option for me.


Joyride’s collection of vintage hat blocks.


A custom western fedora for a client.


Hat stretcher! I’ve made use of these for my wide noggin.


Hat steamer, which is used to stretch the hats!

Rob, the owner, told me that their beaver felt hats started at $350 while rabbit felt started at $250.  I decided on rabbit felt since it was more affordable and I had built up store credit thanks to trading in old vintage pieces I didn’t wear anymore and some thrifted finds.   Our conversation then shifted to the color and overall styling of the hat.  Which color would be most versatile?  Brown or gray? If brown, what shade? Something like dark like whiskey or red-ish like rust? Should the back brim be turned down like the 1920’s? Will the crown be short and tapered like the 60s (with accompanying short brim)?


A variety of true  vintage fedoras from multiple decades.

In the end I went with the rust color, since it was the closest to the 1940’s wide brimmed fedora I wore to the first Street x Sprezza Dapper Day (that is unfortunately too small no matter how much stretching was done).  In terms of styling, I went for a 1930’s look!  This meant a medium-short brim (2″) and tall crown with a center “bash” instead of a C variation. The ribbon was going to be in a dark brown with a bow and triple pleated knot!  These details are ones people seldom think of when purchasing a hat; they make all the difference!


Rust, my chosen fabric, sitting atop the other options.

Why 1930’s fedora style you ask? I just felt that the 1930’s had the best shape of fedora.  Wide brims and shorter, pointy crowns can be pretty cool but they aren’t my aesthetic nor do they frame my face well.  Here’s some of the inspiration pictures for my hat (all 30’s style)

We measured my head (which again was a wide 7 3/8) and put the order in for the felt!  A couple of weeks later the fedora was blocked and shaped!  It looked quite good for simply missing the lining, sweat band, and ribbon!


Rob said he could have the band done in only a few days, so I was back by the weekend to pick up my finished hat.



Note the triple  pleating on the bow.  



Hats made by an established brand (like a vintage one) will have the manufacturer’s logo and seal on the sweatband and lining.  It would be cool if Joyride had one! 

My only “complaint” is that the felt is slightly stiff, since it’s completely new! I’m biased toward vintage fedoras, which have had years of wear to soften up.  I’m confident that I’ll be wear this for years to come and even pass this onto my children, if they share my love of menswear!

Wearing the Fedora

I want to reiterate that it’s important to understand the look that you’re going for when wearing a fedora.  Honestly, it’s still hard for me to try and wear this one even though it’s sharp!  I’ll show you what I mean.  Remember that this fedora is much different than the regular one’s people wear.

With a Modern Suit


That’s the fedora worn with my Indochino Blue DB suit.  Even though the Indochino DB suit is classically styled, something (at least to me) seems off. It might be due to the slimmer pants (that are about 7.75″) or the non-drape cut of the suit jacket.   You guys might think other wise, but it’s still “meh” to me!  Note that the styling is still 30’s, with the striped spearpoint shirt, dot tie, and exploring pocket square.


This fedora doesn’t really work with the whole slouchy sprezzatura look.

Indochino DB Suit, custom spearpoint shirt, 1930’s tie, Zara Derbies

With a Vintage Suit


Doesn’t that look much better? Here it is worn with a vintage 1940’s suit.  Note the stronger shoulders, suppressed waist, and wide leg pants.  It also helps with the “fishmouth” peaks (droopy peaks) and wide set button placement.  As we’ve learned in my previous post, button placement makes a world of difference.


The outfit is very similar  to the previous one but it is the actual suit details that have changed.  In addition to the lapels and buttons, you can just tell that the fabrics are different. The Indochino one is a worsted wool, but it’s very fine and shiny; that’s an issue I have with a lot of “modern” fabrics.  The 40’s one is also worsted but much heavier and textured. It drapes differently and adds an extra dimension to the outfit.  Plus it also has a dope pattern.


Pattern mixing the way Ethan knows how.

1940’s Suit from Paper Moon Vintage, custom spearpoint shirt from Natty Shirts, 1940’s tie (ebay), Florsheim Imperials (thrifted)


Rob at Joyride: Vintage for Men did a fantastic job with this fedora and I’m proud to add it to my small hat collection!  He’s done great work stretching out my previous hats but we both knew the only way I’d be happy was if I got a custom one.  I’m definitely going to be wearing it to Dapper Day this weekend!

I don’t want to discourage you guys from wearing fedoras, but please be conscious of what you’re doing.   It really takes a mastery of style in order to pull one off, especially if yours is vintage.  I’m going to try and make more posts with the fedora in them, just so you guys can see how it works with my vintage-meets-modern style.  Based on this post, you’ll note that even a classically styled modern suit can be a bit odd with a fedora.

It could just be me though, so I’d love to hear your thoughts on fedoras! Feel free to comment your own interpretation of it! Does it work in both outfits? What could I do differently with my modern suit to make it work better?

Always a pleasure

Ethan W.

Street x Sprezza

Photography by Ethan’s tripod


  1. Thomas Henderson · April 18, 2017

    Nice hat! Very James Cagney style. If you want to see a guy who can really wear a fedora with contemporary suits, check out Andy Poupart #styleafter50.


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  3. Shea Robison · April 27, 2017

    As I have said before in a previous comment, even though vintage style is not my thing I keep checking out your blog because of your enthusiasm and your attention to detail which informs me about so many things I would have never noticed or been privy to otherwise. Your discussion of fedoras here, including your own doubts and reticence, was definitely another worthwhile read. Keep on keepin’ on.


  4. Hugh · April 29, 2017

    Questionable English aside, this assertion; “fedoras caught in in the late 20s, making them inaccurate for a roaring 20s event” is evidently false, with plenty of photographic evidence demonstrating the popularity of the fedora as a more casual alternative to “hard” felt hats from pretty much the 1890s onwards. A nice example can be seen in the photograph below, taken in 1921, where all the felt hats seen are fedoras.


    • Ethan W. · April 29, 2017

      I’m sorry, it should say “caught ON in” not “caught in in”.

      And while I know that fedoras have been around since the 1890s (not always referred to as fedoras), I personally wouldn’t use them in Gatsby events. This is also due to the fact that most of the time men dress like the 30s or 40s for most Gatsby/Gangster parties when style (and certainly the style of the fedora) differed greatly between eras.

      There are also plenty of pictures of the early stages of the depression where men are in fedoras and that certainly points to the use of fedoras in the early 1920s (or even late 1910s). I am simply not a fan of the use of fedoras in 1920s related events (Gatsby included) since I don’t feel like they are true to the era or even executed well.


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  9. Robert · October 20

    Hi. I always wear a fedora with modern suits. Summer or winter in a dayli bases, and that’s in the last 39 years. I’m 57 now. And always feel right. And fun. Best regards. I just love the hat. Great job.


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