As fall approaches, it’s about time that we talked about this classic piece of headwear. Apparently, going from an almost-full on rejection to a newfound appreciation is the theme of this blog!

For a vintage-inspired menswear guy/blogger, it seems that I’ve tried my hardest to distance myself from the fedora. It’s probably due to the fact that I’ve never been super comfortable wearing them, thanks to all the neckbeard/cosplay connotations that come with them. As you guys know, I’ve never been one to dress in full period-accurate wear (other than vintage events and the occasional dapper day), so it never really made sense for me to wear a fedora often (even though I actually own a few). They “worked” for vintage stuff, but I couldn’t take myself seriously in them. It was too much of a costume.

2013 Ethan was very unsure of his place in the menswear world.

With that said, I’ve always envied guys who are able to pull it off despite it being a bit of an anachronistic Ethan Newton and Cody Wellema come to mind; both of these gents have a vintage-meets-modern aesthetic that really tickle my fancy. There’s something authentic about these guys that I couldn’t achieve for myself when I wore fedoras. It’s that essence of style that marks it different than the “kid in the domo shirt and stetson fedora”.

I love headwear, but there was something intimidating about the fedora. That’s why I always preferred berets and bucket hats since they always add something “extra” to an outfit while maintaining a slouchy, almost irreverent elevant vibe. However, this fedora-shunning attitude began to change as I started to hang out more with Cody Wellema. I’m a freelance/hobbyist photographer and I occasionally do some shoots with Cody; we even did a podcast/blog post about him! Some of the work has been paid, but most are just a couple of shots during friend conversations. Cody was gracious enough to gift me two hats, the latest of which was featured in a small hangout-turned-editorial in our town of Pasadena.

I really loved the hat he made me and it actually made me start to think that perhaps fedoras aren’t bad after all. I mean, like the other headwear pieces before them, they are a functional item, providing protection from the elements. They also provide instant style points, and help frame intentionally, separating it from the floppy beret and bucket hat. Intrigued by how well my latest Wellema fedora came out, I decided to take the deep plunge and write a bit on the subject.

Vintage Fedoras

I actually wrote about hats for Styleforum a couple of months ago, but felt the need to revisit them for the sake of this article. Now, it was pretty much commonplace for a man to be wearing a hat during the 1900s-1960s. Homburgs, derbies, bowlers, and top hats were the name of the game until the felt fedora changed things up in the 1910s and later. The fedora was worn with a variety of outfits during the Golden Era (1920s-1940s), whether it was workwear, casual, separates, or full suits.

Like lapel styles, the details of the fedora changed throughout the decades. For starters, a pinched crown with defined ridges, and a downturned (on all sides) semi-wide brim was common for the 1920s. Tall/narrow crowns with a center crease remained in the 30s, but the brims got shorter and featured the snap front and the upturned back. Things mellowed out in the 1940s-1950s with a more “whole” look with C/teardrop crowns becoming more popular, until getting really small in the 1960s and then large again in the 1970s. These always carry over each decade so don’t take what I said as law; even things like ribbon width and crown pinch vary. As a whole, most fedoras made today are a mix between the 1940s-1950s styles and the 1970s proportions. The following pictures help illustrate these details I hope.

Say what you will about fedoras, but they certainly look really good on those old guys. There’s something about the cocked hat and a sharp suit that really looks cool. I’m a little obsessed with how cool a hat looks when its turned, providing shape to the top of the head through a crown and an upward angle, from the snapped brim and upturned back.

Wearing Them Today

The main issue when people wear fedoras today is that it tends to look like a costume. By that I mean that people choose fedoras and flat caps because they’re intentionally trying to go after a certain look and they think that the hat will get them there. Obviously I’m guilty of “menswear cosplay” since a lot of my outfits are directly lifted from Fellows illustrations to what F.E Castleberry captures for Drake’s, but I think that natural authenticity plays a big role.

I’m drawn to my contemporary inspirations because of how natural (and slouchy) they make tailoring look. They don’t have the neckbeard attitude of superiority when it comes to suiting. I can’t count how many times I’ve seen a guy think he’s all that when he’s wearing as suit and a fedora, saying that class is better than swag (I’m looking at you, youtubers). My guys wear a DB bespoke suit like a regular dude wears a denim jacket: lived in and natural. And that’s how you should approach it.

Looking at the vintage pictures made me realize that these guys are wearing fedoras like we would wear a bucket hat, beret, or knit cap. Sometimes it’s perfectly put on, others it’s lazily cocked back. That’s the biggest draw of the Golden Era and it’s right temperament to have when wearing a fedora.

This was also the theme I had when I wrote about fedoras for Styleforum.

You’ll also notice that a fedora “fills out the head” due to the brim and crown. Sure a bucket hat might be slightly similar in that regard, but it’s floppy and can change shape; a fedora has a very defined crown (with ridges, pinches, and creases) and a slightly stiff brim that snaps down in front and turns up in the back. When you wear it with most modern clothing, it results in being top (head?) heavy. I guess that’s why a brimmed hat works best with vintage and full-cut classic menswear, since the hat offsets the slightly bulkier silhouette. It’s also why hats seem to call for heavy fabrics and layers to help add to that fuller size.

When choosing or designing your fedora, brim and crown treatment is up to personal taste and depends on your face shape or desired era. Basically a taller crown is older, while most modern fedoras have shorter crowns. Ribbon width is up to you, but traditionally, thinner ones are more casual; best to keep that in mind if you want something versatile. I think there are three main types of fedoras (mainly just colors) that will get you through most styles. Remember to wear at your own risk; I’ll admit that I don’t always have the confidence to wear them out!

Grey

Grey is the conservative standard and will work for almost any sartorial look. It’s not dressy like black (which like a black suit is a hard one to wear outside of minimal/street outfits), but not as casual as brown which allows you some leeway to wear it as you please. I like to think of it as the equivalent of a grey flannel/fresco trouser, since it will get you out of almost any situation. The shade of grey is up to you, but I like a dark brownish-grey so its a bit more versatile; a light grey is nice, but much more suited for dressy looks.

Mine is a 1930s styled Wellema, with a thick black ribbon. It’s actually one of Cody’s RTW ones so it’s not custom made; it just so happened that it was my size. Originally, it had a center crease, but I had it adjusted to a tear drop and shortened the crown to better fit my round, wide face. I’m still not completely sold on it, but I will say that looks pretty great in these outfits.

Brown

Brown has to be my favorite one. The Indiana Jones connotations will be made, but I think it’s so much more than a costume hat. Like a brown suit, the brown fedora is the casual-yet-dressy alternative to the grey, able to slide easily between workwear and tailoring easily. I really love it with tailored layers like an blazer and military jacket, but the chambray shirt combo also gets me. Like most things, shades of brown depend on your personal style, but I will always prefer a dark brown. Personally, I wouldn’t wear it with a brown suit (since it’s too matchy) and would prefer it with navy or grey suits, though separates is always a good choice especially if your jacket has texture or pattern.

I actually have two brown fedoras! The first one was an early 1930’s silhouette (high crown, shorter brim) made from a rough, brown-red felt; I don’t wear it too much anymore. The second one is another Wellema (seen above), this time completely custom and designed by me. It’s similar to the Bryceland’s Bogart which is a 1940s tyle, but mine has a lower crown, less of a pinch, and a narrower brim, all of which fit my face better I think. It’s my newest acquisition, and I’ve been wearing it a lot this past August though I can’t wait to do it right in fall/winter.

The Tan/Silverbelly or Western Style

While I love my brown fedora, it’s really the tan/western style one that remains the most versatile and popular among the greater menswear world. It’s probably because it’s inherently casual due to it’s light color (providing great contrast), thin ribbon, and upturned brim. You can think of it like a bucket hat or knit cap, adding an extra touch to an already casual outfit or it act as a subversion to a traditional tailoring; mixing and matching is always preferred. You’ll see this mainly worn by vintage workwear/Americana enthusiasts at Inspiration LA, but suited-ish guys like Ethan Newton and David Coggins also rock it.

The one I wear is an 1940s-1950s Stetson that I got at Paper Moon Vintage, one of the first vintage stores I’ve been to. It’s got a shorter crown and a pretty wide brim compared to my other fedoras, so I always make sure that the brim is turned up so it doesn’t look like a zooting one. I don’t wear it too often as I think my bucket hat makes a better casual outfit than the fedora, but I do break it out every once in a while; you’ll probably see Spencer actually wear it a few times.

If you’re interested in one for yourself, the Stetson silverbelly or stratoliner are a good choice (which is what Ethan Newton owns or has made hats after). You could always just get Cody to make one for you!

Others

Besides the basic grey and brown, there are always other colors to choose from! Things like deep indigo to black are perfectly acceptable, as long as you’re confident to wear it. The only other color I own is a black 1930’s one, that I really never wear, since it’s such an odd color. However, the process of writing this post made me consider exploring it again and finding a good time to wear it.

When wearing hats outside the classic pieces, I think it’s best to keep your outfits fairly minimal or to lean in completely on the casual vibes. The important thing is let your hats accent the outfit, rather than it take the front of it. Minimal looks are a really good direction to go in.





At the beginning of quarantine, shortly after covering Holmes’s Bohemian- Victorian look, I eventually decided to commission a black model from Cody Wellema. I didn’t deviate from the blog, as I found it perfect for my faceshape; the only detail I changed (apart from the felt and ribbon color, obviously) was the style of ribbon knot.

You may be wondering why I got a black fedora, considering it’s rather unfortunate connotations; my only answer for you lies in the badass pictures of Ethan, Kenji, and the rest of the Bryceland’s team above. It just has an edgy, rock-and-roll aesthetic to it, which I genuinely enjoy doing in classic tailoring. Wearing it with a tie can be a bit challenging, but it’s right at home with a sawtooth shirt or an open sportshirt.

Funnily enough, I think I like wearing it more than my brown one, just because it’s cooler. I just can’t wait to get it beat up and just as soft!

Conclusion

Hats are always going to be controversial; you guys should have seen the comments I’ve received from the bucket hat and knit cap articles. As I’ve said before, they are usually functional and utilitarian with the bonuses of providing style point to an outfit. The only difference is that fedoras come with even more of a stigma, as they are the most dressy accoutrement the comes to mind when wearing a suit. Guys think that wearing it will instantly make them dapper and it usually results in the hat coming off as affected and turns the outfit into costume rather than something natural (at least in my opinion).

They key to pulling them off is to think of the fedora like any normal hat: a bucket, a beanie, or a cap. Not only is that how the guys today do it, but it was pretty much how the Golden Era did as well. If you approach it with that attitude, then the style will fall into place. I use the same thing for tailoring; it’s just an outfit to me, not an elegant, luxurious suit that makes me the best dressed guy in the room. Adding an air of (dare I say it) sprezzatura will help you come out on top. And at that point, it won’t matter what anyone else thinks, as long as you’re happy with it.

If you’re getting some for yourself, just keep in mind your face shape, as that plays into how the crown height and brim width. Obviously it’s better to go with a custom hatmaker, but vintage ones can be good too if you can try them on before buying (avoid places like Goorin Bros). Most 1930s-1950s ones can be flattering but I’d stay away from the stingy 1960’s fedoras as it doesn’t leave you any favors. Colors are up to you, but grey and brown will get you through most tailoring while the tan/western/Silverbelly is the most popular and versatile.

I hope this article has provided you with enough inspiration and commentary on fedoras to help you consider trying it for yourself! It took me a while to finally be comfortable with it, but I now really enjoy my Wellemas and the outfits I’ve created with them. I still can’t believe I wrote an entire article on fedoras; it’s like I’ve come full circle, back to good old 2013.

Always a pleasure,

Ethan W.

@ethanmwong

Street x Sprezza