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.

Undeniably, fedoras can be one of the most affected things a man can wear. Anyone who wears one would probably admit to liking the cocksure look of a fedora more than the actual function of one: Sun shield?  Hair-loss hider? But fedoras are also the ultimate test of individuality. You just can't pull off wearing one unless you are unusually confident, daring, and nonchalant. All that said, men who sport hats of any kind can get away with just about anything as far as I'm concerned.

This May at the Costume Institute benefit at the Met, where women parade around in couture like pretty peacocks and men serve merely to escort them, I walked away from that evening realizing that the person who had stunned me was Nick Cannon, an MTV host and movie actor. He was wearing a traditional black tuxedo, white shirt, and long black silk tie (secured in a thick Windsor knot—bonus points for that) and above all, he topped the whole look off with a sleek black-felt fedora. He was elegant, a little bit street, and sexy all at the same time. His look reminded me of a Bing Crosby photo from the sixties that I have long admired. A male friend asked me recently if I would ever want to make out with a guy in a fedora (were I not married, of course). And my answer was a resounding yes, given that the hat came off first. I'd never heard of Nick Cannon before the night of the Met Ball, but you can be sure I'll pay attention whenever his name comes up now.

Nick Cannon (with Selita Ebanks) at the Costume Institute Benefit at the Metropolitan Museum of Art, May 2007. (Getty Images; May 2007.)

Bing Crosby, pairing a fedora with a tuxedo in the 1961. (Getty Images; January, 1961.)

Sam Buffa, the co-owner of Freemans Sporting Club barbershop and also a member of the U.S. national motocross team, sporting the straw fedora that he almost never takes off.

A groovy Williamsburg dude, adopting a surprisingly conventional look. The striped ribbon keeps it from looking too straightforward. McCarren Park, Brooklyn, July 2007.

Brigitte Bardot with her then husband Gunther Sachs, in 1967. You can't do much better than that. Deauville, France, 1967. (Roger Viollet/Getty Images; January, 1967.)

Sunday Best at its best. Kansas City, circa 1955. (Getty Images; January, 1955.)

This guy is borderline too hipster for me: It's all a bit too cool for school. He pulls it off though. Just. Houston Street, NYC, 2007.

There's no question that Mick and Keith (captured here with eternally cool Anita Pallenberg) were trying very hard with their fedoras. It doesn't matter though. They look amazing, and they've got style to spare. Heathrow Airport departure lounge, London, 1968. (Getty Images; December, 1968.)

What I like about this guy is that he reminds me of someone working in an Italian meat shop (think Satriale's from The Sopranos) in the 50's. He looks authentically old-school even though he actually works the counter at Magnolia Bakery, a cupcake shop in the West Village. Bleecker Street, NYC, May, 2007.

I think this man looks cool in a very unassuming, unpretentious way. My editor at Men's Vogue, however, remarked that he could either look like a horse trainer at an English racetrack (good) or a Midtown OTB customer (bad). You decide. Fifth Avenue, NYC, July 2007.

Well, you already know how much I love Gregory Peck, and this candid shot of him with David Niven certainly doesn't disappoint. In fact, I can't find a bad picture of Gregory Peck. If you find one, please don't send it to me. On the set of "The Sea Wolves: The Last Charge of the Calcutta Light Horse" in India, 1980. (Getty Images; January, 1980.)

Ilie Nastase and Jimmy Connors in wide ties and fedoras. 1970. (Getty Images; January, 1970.)

In case you couldn't tell from my previous blogs, I have an obsessive habit of looking through vintage photos online. For me there's no greater thrill than looking through 67 pages of, say, run-of the-mill men in tuxedos when something out of the ordinary stops me -- jeweled studs! -- and speaks volumes about personal style.

So the other day I was walking on Madison Avenue, looking out for men who catch my eye, and I noticed in retrospect that I didn't clock any men wearing ties. I do like men in ties -- a lot -- but I wasn't really feeling it from the men I saw that day. So when I got home I went looking for inspiration online and did a men-in-ties search from 1940 to 1985. Looking through my selections, I was far more interested in the men who clearly wore ties by choice, as opposed to obligation or convention. Musicians like Bryan Ferry and Mick Jones, screen legend Michael Caine, sixties photographer David Bailey -- they all wore uncompulsory ties to great effect. These men had no real reason to be wearing a tie other than choice, and this choice alone brought something different and more personal to their look. A tie worn under a sweater, or with no jacket and rolled-up shirt sleeves, or even just a tie with a loose knot, all looked exciting to me.

Conversely, I also feel something for a guy who is a proper, devout tie wearer and wears one regardless of his location or situation. Coming out of my apartment the other evening, I saw a very attractive and elegantly dressed older man standing outside The Box, a scandalous dinner theater on my block that is more known for local Lower East Side hipsters than Upper East Side patriarchs. I asked a friend and learned that he was Lewis Lapham, former longtime editor of Harper's magazine. Even though his tie-wearing surely stemmed from convention, he certainly didn't need to be wearing one on Chrystie Street, no matter the occasion. Lewis Lapham is a rare bird, and hopefully not a dying breed.

 

I didn't get the chance to ask this guy where he was going but, judging from where this photo was taken (just outside the Ralph Lauren offices), I'd be willing to bet that he works there. He looks the part entirely -- to great effect, mind you. Madison Avenue, NYC, July 2007.

Filmmaker Wes Anderson looking rather underdressed in a tie at a film premiere in 2003.  (Getty Images, March 6, 2003.)

This picture from the eighties of Bryan Ferry's casually-worn tie gave me the idea for this blog.  (Lynn Goldsmith/Corbis, 1980s.)

A tie with jeans and sneakers can be scary, but this guy pulls it off by keeping it simple and clean. SoHo, NYC, July 2007.

Topper Headon of the Clash helped the uncompulsary tie become an iconic rock star look. 1980s.  (Getty Images, January 1, 1980.)

The American rock band, The Byrds, 1970. (Getty Images, January 1, 1968.)

A friend, set designer Sebastien Sergeant,who lives across the street from me. Forsythe Street, NYC, May 2007.

A white shirt and black tie and oversized sunglasses became legendary actor Michael Caine's signature sixties look.  (Getty Images, May 14, 1965.)

I love the Army jacket over the shirt and tie. The Automat, London, June 2007.

English fashion photographer David Bailey, 1967.  (Getty Images, May 14, 1965.)

Lewis Laphan outside The Box. Chrystie Street, NYC, June 2007.