Sperry boat shoes are the only shoes I'll ever need for summer - here's why I buy the same pair year after year

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Owen Burke/Business Insider

The author's current pair of Sperry boat shoes.

• I've tested dozens of shoes this past year, but when spring weather finally arrived, I reached for my old faithful pair of Sperry Authentic Original Boat Shoes.
• In the footwear department, it's hard to beat a trusty pair of rubber-soled, full-grain leather moccasins, especially for less than $100.
• There's nothing flashy about my Sperrys, and that's what I love most about them. They go with almost any outfit, they slip on as easily as slippers, and they kind of feel like them, too.
• Let the cynics all talk. No one has to know how comfortable we are.

I know, I know. There are more stigmata attached to Sperry boat shoes than you or I would care to count or dissect, and, let's face it, they may not be wrong.

But, find me a soft, full-grain leather moccasin that'll last a few hard years, one whose insole is soft as suede and grows ever softer with age, whose leather outsole bears the springiness of a freshly trimmed Bermuda-grass lawn, and whose price tag, perhaps most importantly, does not break $100 (at least not before tax), and maybe I'll reconsider next year. But I doubt it.

Owen Burke/Business Insider

Field notes

My testing process with this particular pair of boat shoes has taken me from the boatyard parking lot to the top of the mast and back, and along docks and piers.

Yes, they do survive a life aquatic, but that was never up for debate. Just the same, I've had them up and down avenues and across the mean streets of Manhattan (and countless other large cities), in and out of the East River (don't ask), along with arguably cleaner, less turbid (and noxious) waters.

Still, that's not at all what makes them the be-all, end-all article in preppy footwear. While Sperry's boat shoes may have "started it all" (direct quote from the brand's website), it's their timelessness and fashionable functionality that makes these the most spotted kicks in New England - they do, after all, go with any color chino or denim, baggy, or thin, and short of a tuxedo, they'll stand proud anywhere.

Specs

The Authentic Original Boat Shoes, as their name suggests, come in what is, more or less, the same design as they originally did, in 1935.

They're still hand-sewn, full-grain, unlined leather, and they break in without losing a stitch. Then there's the 360° lacing system that lets you tighten up or relax support as you like, and the simple-yet-elegant (and necessary) finishing touch: rust-proof eyelets. (I ended up with the laced version this year, but they can be a pain, unless maybe your an artist. Here's a guide to all the different ways of lacing Sperrys by the brand itself, because, apparently, it can get complicated.)

A relatively recent and modern addition, Sperry's boat shoes now come with open-cell foam Orthalite insoles, which are thin but do just enough work to keep you comfortable without losing touch with the deck (or ground). (Pro tip: If you're really planning on walking a lot in these puppies, grab a pair of Dr. Scholl's inserts.)

And, of course, we can't forget the razor-cut Wave-Siping traction on the bottom of the outsoles. Sperry's Wave-Siping outsoles are made with a series of small wavelets and deeper grooves, which, as West Marine explains, "disperse water and give you incredible grip." This is what keeps you upright on the slick - wet or dry - deck of a boat when a pair of Air Jordans would only do you in. Just be cautious. When you notice yourself starting to slip, it means your soles are done. My impossibly frugal father (the man who graced me with my very first pair of boat shoes) often tries to refresh his with a belt sander, but, between you and me, it's never worked, nor will it ever.

The bottom line

This is not to say I haven't liked any of the other shoes I've tested; I have, and I'm wearing some now. But if there's one shoe I must have, each and every summer, if I'm going to wear shoes at all, it is without a shadow of doubt, the Sperry boat shoe. Soft and form-fitting, yet capacious, if I have to incarcerate my feet for the better part of the day, this is the minimum-security detention center for which they're willing to make a compromise.

Shop Sperry's men's boat shoes, available at Sperry, $47.99-$374.95

Shop Sperry's women's boat shoes, available at Sperry, $47.99-$140

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