Remembering Skateboarding’s Unfortunate Fedora Stage

We’ve all been in that place. Images of ourselves from years back are somehow unearthed from a shoebox in the attic or a dormant Photobucket profile. In the best case scenario, we discover these photos by ourselves, allowing for the opportunity to salvage the few that are decent enough for a shameless #TBT, and then mercilessly destroy the rest before they see the light of day. However, most of us probably encounter something closer to the worst case scenario, which is the uncovering of the relics of our foolish youth while others are around, leaving no time at all to filter out the truly incriminating photos and forcing us to explain all of our prior follies to the face of ruthless ridicule. The horror.

Some things are easy to dismiss as fads of the time, like baggier pants or an absurdly excessive chain wallet. Others are not quite as simple to explain, like that not-at-all-ironic Goldberg shirt you seem to be wearing in every photo, or that two-toned bowl cut where the top is piss-yellow and the sides and back are your natural color, or that pair of white and pink Etnies Czars. All of these decisions seemed to make sense at the time, and we can even argue that something “was only cool in our town and not in others”, but all of these justifications seem to fall short as we ourselves take in a heavier glimpse of our past and cast judgment. More and more, it seems as though one of the benchmarks of growing up is the process of looking at the things you did in the past with a “What in the hell was I thinking?” expression.

Skateboarding has experienced this phenomena a handful of times in its storied history. Certainly, we all look back at the days of Lycra jazzercise outfits on a vert ramp or the repugnantly enormous pants / small wheels movement and think “those were dark times in skateboarding’s past” (although I’m not sure Gilbert Crockett got the memo on the latter). What many of us fail to notice or acknowledge is one of the most awkward and unnecessary periods of skate history occurred in just over the last decade, one which continues to rear its ugly head into our lives this very day. I’m of course talking about the Fedora Era.

No one was safe from the fedora trend. Not even the Boss…

The honest truth is that a lot of shitty products get marketed towards skateboarders, and some of the worst products out there have been in the headware department. Companies like Neff offered up hot piles of snow-bro garbage like giant floppy beanies or baseball hats with moveable brims on an internal track, all of which come in blindingly-saturated neon colors. Elsewhere, we’re led to believe that products like the Tom Penny hat (beanie with a brim), the gardening/sun hat, the bucket hat, and now the ‘dad hat’, are all items that not only look cool but also have stylistic permanence beyond three weeks. While all of these dome covers look genuinely stupid in their own unique way, none of them have come close to the level of unadulterated idiocy as the skate-fedora.

To be clear, we’re not talking shit on the person who wants to dapper things up after they put the board away; what you do on your own time is your business. Lace up those wingtips, throw on that wide brimmed Stetson and dance to your heart’s content. We’re talking about the folks who feel that their porkpie would be the perfect accessory to their outfit as they’re walking out the front door to go skate.  It’s not, and you should leave it at home. Putting on a fedora to go skate is like bringing a guitar to a session; it’s clear that you had other plans for the day that didn’t include skating, and you’re really being more of an annoyance to the group than anything else.

Moving on, the backstory of how the skate-fedora was born is a little hazy, but in the early to mid-2000s, more and more companies began to include dress hats in their apparel catalogs. By 2005, it seemed as though you couldn’t flip through a CCS without coming across a dozen or more fedoras from a handful of brands. What is interesting about the rise of the Fedora Era was that the quality of the hats that were coming out wasn’t even that great. Often times, you would find a litany of standard fedoras in fairly tawdry materials like corduroy or canvas, along with a few ugly plaid trilbies peppered in there for added tackiness. Looking back on it now, maybe it was less about the quality of the product and more about the newness of it all, or maybe filthy skateboarders just want to feel like they’re at the Kentucky Derby once in a while. Regardless, it would have been one thing if these hats were being marketed towards skateboarders as a ‘lifestyle’ product for post-session activities, but things really began to change when photos started popping up in magazines of well-respected skateboarders doing professional-quality skating in various dress hats. Guys with indelible reputations like Marc Johnson, Jamie Thomas, and even the seemingly-innocuous Kenny Reed were now poster children for this awful and gaudy trend.

Does a stylish 5-0 (presumably to fakie) with a not so-stylish fedora denounce the ease of such a beautiful trick?

As time progressed, the Fedora Era in skateboarding shifted. The Baker and Hellrose crews injected themselves into the Hollywood social scene, which brought a variety of external fashion influences into the skateboard world. Around that same time, brands like Brixton helped to normalize the existence of dress headwear in the skateboard market, and that in turn ushered in a whole slew of skate-hat styles.  There is the straw hat, which is a favorite of Christian Hosoi and Chris Pastras. Then there’s the Newsie, enjoyed by the likes of Patrick Melcher, Jason Adams, and everybody’s favorite shit-talker Giovanni Reda. Then you have the Sailor hat, which could often be found atop the heads of Matt Ball and Braydon Szafranski. And for the brave few, there’s the Hipster Halo, which is a wide-brimmed felt hat that was a perfect addition for the hybrid hesh/gypsy style of Ali Boulala, Ragdoll, Gareth Stehr, and this era of Jim Greco. With the fancy hats came the fad of skating in vests and flowing puffy shirts and the like. We’re not going to get into all of that in this article, but we felt it necessary to note that the two trends were definitely not mutually exclusive.

Since much of the pro scene had bought into the dress hat fad in one way or another, it was inevitable that the trend would resonate with the kids watching the videos and reading the mags. Before you knew it, every plucky little shit at the park was either wearing a cheap trilby or some awful plaid monstrosity, and every high school valley girl was flocking to their local Zumiez to pick up their new SK8R GRL accessory.

Repeat offender, Kenny Reed. Rumor has it that he’s still out there with one on- without the feather though. That’s overkill.

In an almost poetic fashion, the Fedora Era seemed to leave skateboarding as swiftly as it arrived, and while there is still plenty of photo and video evidence to remind us of its existence (especially in the case of John Rob Moore), it appears that most people got wise about keeping their fancy hats on the rack until they were done skating for the day. As one would expect, there continue to be individuals straggling onto the trend and milking it for all it was worth. Hosoi skates in fedoras far more frequently than any of us would like to see, and it makes those layback grinds just a little harder to enjoy than before. Similarly, Greg Lutzka has made his Monster Energy-laden fedora a staple in his contest attire, which is nothing short of vomit-inducing corporate shillery. Every so often, little embers of the fad will pop up, but the winds of change in skate fashion seem to be blowing back towards durable working-class attire, so it’s unlikely that we’ll see a fedora resurgence anytime soon.

As we finish taking a look at the heyday that the skate-fedora had in our presence, we recognize that we unearthed quite a few cringe-worthy photos of some of our favorite pros, like the one of Andrew Reynolds dressed like a pimp next to Ryan Gosling. Obviously we mean no harm in the examples that we provided, and we also feel that we may have painted a picture with broad strokes so as to imply that all skateboarders are forbidden from wearing fedoras or other dressy hats, at least while skateboarding, and that couldn’t be further from the truth.

The following skateboarders are exempt from shame and ridicule for wearing fedoras, on or off the board. Here’s why:

Mark Gonzales

As skateboarding’s official Crazy Grandpa, Gonz has taken to quite a few grandpa-like habits, such as smoking cigars, hanging around NYC parks yelling at inanimate objects, and dressing himself with complete disregard for aesthetic cohesion. As such, we’re pretty sure that encouraging him to stop wearing fedoras would only make him do it more.  Plus, we wouldn’t have photos like this one.

Duane Peters

1000% Guarantee – he doesn’t give a shit. We’re not gonna rock the boat.

Jason Jessee

He is exempt for the sole reason that he deliberately wears a beanie (often orange) under a fedora, which is by far the ugliest way that one could ever be worn. The sheer gall of Jessee to double down on the wearing of a fedora and then to completely fuck with it even more by adding a beanie shows that he, like the Master of Distaster, truly does not care one iota what another person thinks. It just goes to show that attitude is everything. If you convince yourself that what you’re wearing as the coolest shit there is, all of the sudden it becomes the coolest shit there is and there isn’t a person alive who can refute it. We salute you!

Matt Hensley

Not sure we even have to justify this one. If ever there were a proper gentleman to appropriately don a dapper hat, it would be Matt Hensley. Enough said.

Written by Mayor Grimble
Photos by Andy Stoffo
Stay updated with us on Facebook
Chat with us about Skate Shoes on Twitter
Tell us to repost your photos on Instagram


  1. Ghettoblaster

    December 12, 2016 7:18pm

    Ahhh glad to see the gonz exempt.

  2. Dave

    December 13, 2016 11:25am

    Come on! Hosoi gets a pass!

  3. Ross Dailey

    December 14, 2016 5:54am

    Tyler Bledsoe’s back tail around the U ledge … he was rocking a fedora.

    • Ripped Laces Staff

      December 14, 2016 8:11pm

      We wanna count it, but it was a glossy bucket hat. Shit, almost just as bad :/ #Conflicted

  4. jof

    December 15, 2016 5:34am

    y’all so judgmental.

  5. JD

    December 16, 2016 10:08pm

    Is anyone gonna point out that Reynolds’ hat isn’t a fedora?

    • Mackhel

      December 19, 2016 8:44pm

      Thought it was mentioned in the article further down that it was not a fedora but your right. It wasn’t. He’s wearing some type of celebrity hat that honestly doesn’t look as butt-ugly as a fedora. The fedora is impossibly hilarious and looks completely dumb. The beanie with a brim is also in the running for most dumb

  6. bitchhh

    December 30, 2016 5:09am

    fuck you if you dont fuck with kennys fedora


    January 8, 2017 12:15am

    hipster soma park kids are gonna wear ironic baby pink fedora hats by the end of the year, watch.

  8. George Bullen

    March 12, 2017 1:37am

    Feel like the vertical vampire should be on the exempt list as well, hasn’t he been rocking fedoras for decades?


Leave a comment