Ok everyone, I've been doing a TOOOON of research into this. I come from a minimal shoe with wide toe box background. I've been searching for shoes that have a wide toe box (like, ACTUALLY wide which lets your toes splay) that would at the same time be suitable for skateboarding. I've come up with the following options:
1. SOM Footwear Trailhead OR SOM Footwear HiLite -
https://www.somfootwear.com/products/trailheadThese shoes seem to be the most promising. The 8mm cup sole is thin enough that you'll get good board feel, while being polyurethane material (which is lighter and more durable than vulcanized rubber) that according to SOM has "excellent grip on rocks." This could translate to good grip on griptape as well. The insole of the shoe has a cup sole. Another really cool thing about the shoe is that the uppers are made out of SuperFabric, which apparently is designed to be pretty tough. And finally, SOM does offer neoprene flat inserts (about 14 bucks) which apparently "keeps its thickness and shape even during strenous activities such as running or jumping." Extra cushion never hurts, and this all makes SOM seem like a pretty good option. Finally finally, I did actually reach out to SOM Footwear and they said their customers who skateboard choose the Trailhead or HiLite, which is why I included both. The bulk of my research was on the Trailhead, but I'm throwing the HiLite in there for anyone who may be looking for the same materials of the Trailhead in a high-top option.
2. Icarus Ascent -
https://icarusfootwear.com/products/first-flightI found about these guys from the /r/barefootrunning sub on Reddit, and the owner was doing an AMA. I noticed in the description of the shoes, it comes with three different insoles. One of the insoles is a "Thick Max-Energy insoles (Cushioned heel; 5-11mm thick)," which "offer maximum impact absorption to protect your heel from repeated impacts on modern surfaces like concrete and asphalt. Great for long days in the urban jungle, skateboarding, or if your feet aren't ready for "barefoot" levels of support." I asked the owner about using the shoes in conjunction with their thickest insole for skateboarding, to which the owner said it would be a good idea. These shoes look pretty nice too, tho I'd probably use them for just cruising as opposed to doing tricks, for fear of messing with the white leather upper. Of course everyone else is different.
3. Flux Footwear Adapt High Top with Graphene -
https://fluxfootwear.com/products/flux-high-top-graphene-adaptThis seems like a very durable shoe, from the ripstop fabric upper to the graphene rubber sole. It seems like this shoe would do very well with abrasion, and the sole seems flexible enough to bend with the movement of skateboarding. I reached out to the Flux Footwear people to see if they've been tested for skateboarding, to which they said not yet, but that they'll be hoping to do something like that soon. All in all, with a decent stack height these shoes might not be bad for skateboarding.
4. Adidas The Total Trainer -
https://www.adidas.com/us/the-total-shoes/HQ3533.htmlI like the look of these but not 100% sure how well they'd fare for doing tricks or much beyond cruising. They are weightlifting shoes which seem geared at keeping the foot in a stable position, so the sole may not be flexible or be well-suited to skating. Just thought I'd throw this out there as the sole and uppers do seem durable enough for a skate shoe, and the toe box of course is wide enough.
5. Splay Freestyle -
https://splayshoes.com/collections/freestyle/products/splay-freestyle-coal-shoesThese have been mentioned before, but I thought it worth mentioning again to those who just stumbled upon this thread. The colorway I linked is the most Vans-esque, tho they also do have slip-on versions of their shoes if you really wanna get that yung Vans vibe. These do have a vulcanized rubber sole, and after doing some digging through Splay's instagram a decent amount of their customers do actually use this shoe for skating. Shoe goo or the like is a must for the upper, but the sole seems durable enough, and it absolutely is flexible as well. Have a pair of these myself, they're mad comfy, just haven't taken the plunge in skating with them yet.
6. Xero Prio -
https://xeroshoes.com/shop/activity/performance/prio-men/Braille Skateboarding actually did a video review of skating with these shoes, and you guys can find the link here:
. I actually have a pair of these myself, and with how thin they are I'm surprised they managed to do so well skating with them (save for a few bad landings). Of course, the uppers already had holes in them by the time the video was over, but this could be addressed with something like shoe goo. This video was my lightbulb moment as I had been searching for ages for video evidence of people not just cruising but doing tricks with barefoot shoes. This video proves it's possible with the sole, but not so much with the uppers. Many have suggested Xero's Kelso as another good alternative as well, which I'll link below:
7. Xero Kelso -
https://xeroshoes.com/shop/shoes/kelso-men/What separates the Kelso from the Prio is the 6.0mm FeelTrue sole compared to the Prio's 5.5mm. As well, the uppers of the Kelso are a combination of full grain leather and suede. Not to mention, they look pretty badass as well.
I've definitely been meaning to cop at least one of these shoes (besides the Prio which I already have). If I ever do get one of these (or test out my Splay's cruising and doing tricks), I'll be sure to let you guys know.