Canvas Sneakers Are Hot Again

Made in Japan with siped soles (to prevent slipping), the design is based on the original 1940s USN-issued model. The pedigree speaks for itself, but I’m planning to treat these like raw denim. I’m picturing the indigo slowly fading, beach trips galore, a little sand, a rinse here and there (you menswear heads know the ritual), all leading to that perfect sun-faded patina. Damn—I think I just accidentally revealed my summer plans.

Best Slip-On Canvas Sneakers: Vans Black LX Slip-On Reissue 98 Sneakers

Leave it to a skate brand to rebel against the traditional deck shoe—that’s exactly what Vans did. Style 98, better known today as the Vans Slip-On, rolled onto the scene in 1979 as a laceless canvas shoe marketed as a laid-back alternative to the classic boat shoe. Its low-profile silhouette, padded collar, and slip-on ease made it a natural favorite among skaters, BMX riders, and one unforgettable cinematic stoner: Sean Penn’s Jeff Spicoli in Fast Times at Ridgemont High.

This version’s got grain leather uppers and a canvas lining that ages like a fine denim jacket—the more beat-up, the better. Add a treaded rubber sole and those elastic vamp gussets (the unsung heroes of easy slip-ons), and it’s no wonder people keep multiple pairs in rotation. These go with just about anything, though maybe don’t wear them with a tux unless you’re crashing a beach wedding. For the current temps, they’re perfect with a hoodie and shorts.

Best Canvas Sneakers for Your Boat: Sperry Cloud CVO Sneaker

If you don’t believe a pair of shoes can last a lifetime, just look at Paul Newman (who, fun fact, shared a first name with Sperry’s founder). In his Sperry CVOs, you’ve got young Paul, old Paul, and every charming in-between version of Paul—long story short, this is a shoe that looks good at any age. While Sperry might be best known for its boat shoes, the CVO (Canvas Vulcanized Oxford) was actually the brand’s first launch, making its debut back in 1935. Paul Sperry set out to design a sneaker with serious grip for wet, slippery surfaces—ideal for sailing, and maybe even tiptoeing across questionable pool decks.

Sure, the canvas upper keeps things classic, but the real game-changer is the signature razor-siped sole. Legend has it Paul got the idea from watching his dog sprint across ice without wiping out, which is either genius or a strong case for man’s best footwear muse. So toss on your Ivy League-meets-saltwater cap and style these with chinos, a linen shirt, and a V-neck sweater. If the Converse Chuck Taylor is punk rock and the Vans Authentic is SoCal skater, then the Sperry CVO is pure East Coast coastal prep, with just a hint of dog-inspired innovation.

Best Canvas Sneakers Worn by the Military: US Rubber Military Low Top

U.S. Rubber Co. shoes traces its roots back to the late 19th and early 20th centuries. Originally part of the United States Rubber Company—formed in 1892—this group eventually evolved into Uniroyal (yes, the tire folks) and helped pioneer some of the first mass-produced sneakers in America. Think of them as one of the OGs of the American canvas sneaker game.

Thanks to the sneaker boom during WWI, U.S. Rubber Co. ended up outfitting the U.S. Army. With a factory-specific vulcanization method, tough canvas, and metal eyelets, these shoes were—and still are—built like little tanks for your feet. The military green pairs surprisingly well with just about anything, so treat it like a neutral. Try them with some billowy chinos and a cropped tee for that off-duty vintage recruit meets downtown cool look.

Best Canvas Sneakers for Fashion Guys: Visvim Logan Canvas Sneakers

I’ll be the first to admit that justifying Visvim’s prices can feel like arguing with a brick wall—expensive, frustrating, and ultimately one-sided. That said, I can’t think of another brand that reimagines American classics with the same obsessive attention to detail and fabric sourcing as this Japanese label.