I love Sperry shoes and have about 10 pairs of shoes of various shapes and sizes (including another pair in a different color). I was looking for a casual, comfortable canvas boat and settled on this one. The selection of canvas boats is getting smaller and smaller. They are ready to use and comfortable to wear barefoot. Zero wear required. This canvas feels more like a lightweight twill than a heavy duty canvas and that makes it a lot more comfortable. Note that they are a bit long for me. I got a 10.5 when I should have gotten a 10 because the heel is too long and slips a bit. The outsole is super flexible. As for the outsole and upper, I don't think they will last that long for the average person given a lot of wear. Me, they will because I have too many other shoes to wear. If you've been walking a lot, you might be able to get Season 1 out of them. Finally, I love the plaid inside - it's a great neat look - hopefully it stays pretty. In general, I'm very happy with them - so much so that I bought another color.
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