As classic as they are, I feel like there came a time in the last decade when (at least for some) loafers fell out of style -- too old-guard, too stiff, too conservative -- and there was the perfect replacement waiting in the wings: the driving shoe. As brilliantly popularized by Car Shoe, Hunting World, and of course Tod's, driving shoes are significantly more sporty and laid-back than their more formal and businesslike counterpart. They replaced loafers for every occasion -- for the office, for the weekend, for church. In fact I bought all our male family friends Tod's driving shoes in black patent leather with grosgrain details to wear with their tuxedos -- they were like an updated version of the black velvet evening slipper. But recently I've noticed the more formal loafer making a comeback, albeit in a more inventive new context. Perhaps inspired more by Michael Jackson's ironic embrace of loafers than the more predictable Wall Street types, many New Yorkers pair the formality of loafers with a more personalized look -- they wear them with scruffy jeans, beards, even Rasta caps. Who knew I'd be singing the praises of Michael Jackson two weeks in a row??

Gary Cooper, with his wife, Sandra Shaw, wears his penny loafers in the most classic context. Southampton Beach Club, N.Y., 1945. (Photo: Getty)

Somehow flip-flops have become an acceptable form of "mandal" for steamy weather, but I still know a large number of men who just won't go for open-toed shoes. What options does that leave for boating trips, beach excursions or even just walking around the city? Well, there are espadrilles, the canvas slip-ons with braided straw soles, and I know they might draw equal opposition. But hear me out, especially if you're an old-world kinda guy. I spent three summers of my late childhood in France, where espadrilles are what everyone—men and women—wear all summer, and I have vivid memories of my stepfather's well-worn version in navy blue. His clothes are always clean-cut, no-nonsense and accompanied by the coolest inherited accoutrements (a Breguet pocketwatch, diamond Cartier studs and countless engraved cufflinks are among his high-end hand-me-downs) and espadrilles fit right in with his style.

I had my doubts that I'd find any men at all wearing them on the streets of New York, but happily I came across quite a few, albeit in updated incarnations.  I saw canvas slip-ons, sans the braided sole, as well as Tom's shoes, whose proceeds help children-in-need get their own pair of Tom's. One breezy discovery was a crochet version of a slip-on, but you probably have to see them (below) to believe that they actually looked good.

At the other end of the summer shoe spectrum is what I have always called Top-Siders, or, as others may deem "boat shoes." In classic form-follows-function spirit, Paul Sperry designed Top-Siders in 1935 to keep you upright on the deck of a boat. Their boat-y relevance peaked in 1939, when the US Navy contracted Sperry to outfit thousands of sailors. And then in the sixties they resurfaced in abundance on college campuses. When I was Creative Director of Hogan, an Italian leather goods company, I was determined to re-invent the boat shoe and bring them back in fashion. The trouble was, they didn't need reinventing. So I just had to wait until the original makers like Sperry and Quoddy Trail in Maine realized what a classic they had and brought them back again. That moment has arrived.

A Slim Aarons portrait of 70's TV actor (and old money Philadelphia WASP) Samuel Chew Jr. in red espadrilles. 1975. (credit: Getty Images)

This guy's espadrilles came from Germany. He apologized for the socks, quite rightly so. Madison Avenue, NYC, August 2007.

JFK with his sisters in 1939. He's really going for it with the ankle straps.

My friend Kate Schelter sent me this photo of herself with Tom's founder Blake Mycoskie wearing their Tom's in Istanbul in July.

My stepfather, Will Stewart, on one of our many summer trips to France in the 80's.

A reluctant subject on his way to the gym. Before he ran away he dropped the name of a friend of mine at Vogue who told me that he is Diego Garcia, the lead singer of downtown rock band Elefant. Spring Street, NYC August 2007.

James Mason, reading a script on the set of Julius Ceasar. 1952. (credit: Time & Life Pictures/Getty Images)

These are the crochet slip-ons I was talking about above. Apparently they came from a Polish men's shoe shop in Brooklyn. I really like them. Bedford Avenue, Williamsburg, Brooklyn, August 2007.

Sam Buffa. Again. He happens to live AND work on my block, and he's got great style. He's wearing boat shoes from Quoddy trailshoes, a family owned, handmade shoes company in Maine. Freeman Alley, NYC, August 2007.

Ezzard Charles, heavyweight boxing champion of the world. 1950. (credit: Time & Life Pictures/Getty Images)

I've been noticing top-siders in new and different colors, like white. Williamsburg, Brooklyn, July 2007.

Famed Interior Decorator Albert Hadley in original Sperry Top-Siders. 1991. (credit: Getty Images)

When Ned Martel (my editor at Men's Vogue) heard I was including topsiders in my blog he showed up to lunch proudly wearing these black ones. I also noticed that he was wearing wayfarers and a white seersucker shirt too. At least somebody is listening to me. Bryant Park, NYC, August 2007.