I Own 20 Pairs of Canvas Sneakers. These Are My Favorites.
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Besides my newfound love offlip-flopsthis summer, another footwear obsession of mine that has grown over the past few years is canvas sneakers. As with flip-flops, I found that I needed to size down for an optimal fit — from my typical 10 in athletic shoes down to an 8 for canvas sneakers since my foot is super narrow. Depending on the season, I’ll wear them with or without socks.
Once I had the sizing figured out, I started paying more attention to what makes a reliable pair of canvas sneakers in the first place. The usual hallmarks I look for are a cotton-canvas upper that is durable enough to get beaten up (since they look better this way), a vulcanized rubber outsole (which makes for more flexible wear), and metal eyelets (what the laces go through). Some pairs have a rubber toe cap for extra protection and comfort.
Within the last five years, I’ve amassed close to 20 pairs — some with coffee stains, scuffed outsoles, and others on ice for whenever a pair in my current rotation becomes unwearable. One thing: You may notice Converse missing from this list. I’ve tried Chuck Taylors in multiple sizes, but even sized all the way down to a 7.5, they still look and feel like a long sailboat on my feet. They’re just not for me. (I do have a soft spot forJack Purcells, on the other hand, as I wore them regularly back in high school.)
Below, a few favorites that I’ve been wearing throughout the summer and will be wearing into the autumn months, too.
A few of my favorites
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A classic, with plenty of grip for skateboarding (or just walking around town).
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The uppers combine cotton poplin and cotton canvas, and the sole is cushy memory foam.
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The bumper gives the toe some extra protection.
Grippy enough for skateboarders (or just everyday wear)
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As long as Vans keeps making its classics, I’ll forever have a pair in my closet. The navy colorway is the ideal middle ground: They don’t get as worn-looking as the white versions, and they feel more casual than an all-black pair. The signature waffle outsole is still grippy enough for skateboarding (not that I’ve tried) but also great for just being out and about (more my speed). It’s also easy to hose off if need be. I also have thepremium version, which has a cushier insole, but I have to wear socks with the heavier canvas to avoid blisters.
For extra toe protection
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I’ve had these for the past two years in a size 8.5, and they’re a pair I wear with socks. One feature I like is the ribbed rubber toe bumper, which gives extra protection to an area that gets a lot of wear and tear.
For a narrower foot
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Sperry’s CVO (Circular Vamp Oxford) sneaker is a design that several other canvas shoes look to as a blueprint. The “Circular Vamp” is the continuous piece of canvas that covers the entire shoe, while “Oxford” refers to the low-cut, lace-up style. I have these in white, navy, and a collaboration they did with BEAMS. I wore the white pair to the beach last year. They’d get sandy, so I’d rinse them off at the foot shower and leave them to dry on our deck. Once they dried, they’d feel crisp and ready for another wear. What I like most about these is that they’re the narrowest of the shoes on this list. I wear a size 8 in these without socks; however, I’d need an 8.5 if I wanted to wear socks with them.
A linen option
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This shoe doesn’t deviate too much silhouette-wise from the Slovakian brand’s run-of-the-millStar Master, but these are the softest-feeling pair because they’re made from 100 percent linen on the exterior, with 100 percent cotton on the insole. The size 8 fits me well, and there’s enough room to wear them with or without socks. I also like how the rubber outsole on this pair is more pronounced than the one on the P.F. Flyers.
The one I own the most pairs of
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I have 12 pairs of these sneakers — the majority are white, with a few navy and gray sprinkled in, along with the brand’s more expensiveFounders Edition Yacht shoe. I get these in two different sizes — an 8 to wear without socks and an 8.5 to wear with them. The insole is made from soft memory foam, and the upper materials are a soft recycled cotton poplin lined with cotton canvas, and I’ve found that these shoes don’t require any breaking in.
A pair with a more substantial canvas upper
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Buck Mason’s ongoing collaboration with Japanese shoemaker Moonstar always sells quickly. This olive pair is from a few seasons ago, but the herringbone canvas used in its current offering remains the same — just in new colors. I will say, these are the stiffest canvas sneakers on the list, and the size 8 still feels a bit too big to wear without socks. I usually reserve these for thicker socks and wear them into November, as the herringbone is more substantial than the usual cotton canvas.
A few more pairs I have my eye on
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The Strategistis designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read abouthere. We update links when possible, but note that deals can expire and all prices are subject to change.
