Easy and Elegant Life

The Search for Everyday Elegance and the Art of Living Well.

The Easy (Sort of Elegant) Summer Foul Weather Shoe


If you think of its pedigree, I’m sure you’ll agree, the classic Sperry Topsider Deck Shoe, while not offering much in the way of arch support, may be the perfect summer foul weather shoe.

Which is funny since the shoe, or — I should say — the sole, was inspired by a winter’s day walk in Connecticut in 1935. That day, Paul Sperry, took his dog Prince, a cocker spaniel, for a walk. It was an icy morning and he noticed that his dog had no problem negotiating the slippery grounds.

Mr. Sperry had been trying to find a good pair of shoes to use whilst sailing his Nova Scotia Schooner. The gum soled shoes popular at the time were slippery on wet painted decks. Rope soled British sailing shoes skated across dry decks.

Curious, he flipped his dog over to examine his paws and noticed the rough pads traversed by small cracks or cuts. So he took a razor to a pair of gum soles, eventually deciding on a herringbone pattern and cemented them to a pair of tennis shoes. He enlisted a deck hand to help test them out and prove that he was on the right track. He was.

The only drawback was that the shoe would cost $4.50. The best sneaker on the market at the time cost $3.75 and wasn’t selling too well. Mr. Sperry convinced Converse to make the shoe for him and an advertising and marketing man (and friend) who worked for McGraw-Hill convinced him (as he had L.L. Bean) to sell by direct mail. Among Mr. Sperry’s first customers was a man named Vanderbilt. Abecrombie and Fitch were the first to buy wholesale and sell to the retail market. The shoe became an American classic.

What makes the Topsider a good shoe for those brief downpours is the water resistant leather upper. Yes, they will eventually soak through and stain your bare feet. But feet dry and they shoe looks better for the weathering. What makes them a good summer shoe is the unlined interior, which I find most comfortable and to which I do not stick even in hot weather. For use with tailored shorts, your non-elastic waist, shorter swim suit or a pair of rolled up khakis, reds or jeans they are hard to beat. Easy? Yes. Elegant? For casual wear, yes. But save them for casual wear.

13 thoughts on “The Easy (Sort of Elegant) Summer Foul Weather Shoe

  1. I have a wonderful portrait of my children dressed casually in an outrdoor setting both wearing their Sperry Topsiders. It is a Strauss Peyton portrait and I just had it rematted and new framing!

  2. All day every day! OK, not to work, sleep, or any sort of “event”, but pretty much all other times. I admit to dressing only one step above the general population, meaning that well fit (“slender” cut, to the top of the knee) shorts and a finely woven polo or OCBD with rolled up sleeves and darkly oiled topsiders are my standard summer uniform unless I have something to dress for. (I am at the beach, which brings down the average dress level to …well, not much!)

    To pve, there are few shoes better feeling or worse smelling than well-worn topsiders; fortunately, the notorious “sider-funk” is easily, cheaply and comfortably eliminated by the “soothing foot-powder” that one can acquire at virtually any pharmacy department or grocery store. I won’t say it saved my marriage, but it did resuscitate the nearly extinct practice of spousal foot-rubs in my house.

  3. Apart from the summery look of the classic boat shoe, the serviceability is an important attraction. Being elegant means appropriate to the occassion and the weather. I see many who are beautifully dressed, but not quite appropriate. A pair of $600.00 Church shoes in a downpour doesn’t look elegant. Toe rubbers look dreadful. I find a pair of penny loafers that have been given a rubber sole perfect for the questionable days. And while it is true that those white soled Topsiders are very casual, they can look very nice with a light seersucker suit for a warm, casual afternoon or evening out. While not quite the original classic, years ago I found a wonderful variation of the boat shoe, I think I got them from L.L. Bean. The leather, laces and sole are black, making it a nifty update of the classic. The wonderful thing is, that on those messy wet days, I can wear them with a tweed sportcoat or blazer, and I have the effect of a dark loafer with water resiliant benefits. Keep an eye out for this variation, hard to find, but very useful.

  4. Love, love Top-siders…an all-time favorite, here. The Colonel, the son, the daughter all tuck their toes into these dandies. I would be the exclusion, as my favorite would be my tasseled Bass Weejuns for relaxed wear.

  5. I used to have a pair of their white elk-hide ones that I adored. The lasted for years and I could wear them all sorts of places. I don’t know if they even make them anymore…

  6. Cap’t Mike, Hmmm, mine are not worn everyday, but they are very old… and no funk! They have a very dry finish, no oil. Wonder if that’s it? Gold Bond everywhere, the Southern secret to surviving summer.

  7. I rarely wear mine… just around the garden or aboard a friend’s boat. But on casual days when it’s pouring outside, I feel secure in knowing that they can take the weather and keep me on my feet. Besides, they feel great to the foot.

  8. I’ll admit to wering them… back in college. And the lace up boat shoes too- from L.L.Beam. Nowadays I wear an old pair of Belgian loafers to bum around in. My shoemaker swears he will not repair them again and not to bring them in. We’ll see.

  9. That’s the rub with Belgians isn’t it TA? There is an Italian company that makes virtually the same shoe with a hard sole. But they wouldn’t feel half as Noel Coward would they?

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