Loafers seem to go in and out of fashion on a regular basis, which is a good thing if you keep your shoes for longer than a season or two, since the return of loafer style is usually right around the corner. We’ve turned that corner this year, and although the chunky shoe is still very much “in”—and brogues and cap toes aren’t going away anytime soon—my preference is for a leaner silhouette for loafing.

This 15 year old pair is by Edward Green, and the shoe reflects the more English or European style of loafer, which is narrower, longer, and with a higher vamp. Works equally well with or without socks (I prefer sock-less in the Spring and Summer), and with casual wear or a slim suit. Heavier loafers, like the Alden Cordovan model or Bass Weejun (Penny loafers) are staples in many a shoe closet, including mine, but there’s something a little more distinctive about a pair that is utterly unlike the thick-soled shoes we see on the streets of New York, London, Tokyo and, of course, Brooklyn.

The polo shirt is a summer staple in most men’s (and women’s) closets, and there are literally thousands of styles, colors, and fabrics out there. The legendary Lacoste crocodile and the ubiquitous polo pony adorn many a chest, but so does the Fred Perry wreath these days, and you can even sport a marijuana leaf on your favorite shirt, if that’s your style (you rebel, you). And of course you can go logo-less at virtually every price point; some of the least expensive shirts are sometimes the most understated.

While the piqué polo shirt, with its banded collar and sleeves, works perfectly on the tennis court (as Rene Lacoste discovered way back in the late 1920s), and is perhaps the ideal shirt to wear (and most elegant) while balancing atop a galloping pony with a mallet in hand, the soft cotton version, with a soft collar, is somehow more elegant when wearing a suit or blazer. Strictly speaking not really a polo; rather, just a more casual short sleeve shirt a step or three above a t-shirt, it’s less common in the right fabric and fit (please, no oversized synthetic blends seen on many golf courses or the occasional dad, with his sleeves hanging by the elbows), but Save Khaki, a small NY based outfit makes what I think may be the perfect version; something that Cary Grant might have worn in To Catch a Thief. Available in thin or wide stripes (in their store, but not on their website; although available at other sites such as Steven Alan’s), it’s a reasonably priced, made in America item that to me is the perfect warm weather shirt—whether with jeans or khakis, or with a trousers and a blazer.

With the imminent release of Baz Luhrmann’s The Great Gatsby, we’re bound to see a revival of certain 1920′s styles—in fact,Brooks Brothers has already unveiled their “Gatsby” collection of clothes and accessories inspired by their role as outfitters to the film. And spectator, or correspondent shoes, are, as expected, in that collection.

They can be difficult to pull off wearing without the look seemingly contrived, but spectator shoes are nonetheless beautiful. They can be part of a full-on vintage 20s look, just like Leonardo will appear, or one can just wear them with jeans–in this case, Peal & Co. for yes, you guessed it, Brooks Brothers shoes, albeit circa 1995, not 2013. And paired with Levis Vintage Clothing 1955 501s, at Cubana Social, Williamsburg, where no look is ever contrived. 1925, 1955, 1995, 2013….and the look goes on…

Narrow ties are great, with the right outfit of course. They look silly with double breasted suits, and sillier if you are styling a 70′s sport coat from your dad’s closet. There have always been narrow ties, even at the height of 70s excess, and I have a couple I’ve kept for years. (The advantage in keeping old ties is that one day they will be truly unique, an you will never appear in the same (or similar) tie as someone else at a party, or at work.) Ties allow us to express individuality, although I tend to draw the line at ties that scream “look at me!”

So stripes in unusual colors, plain solids, woven patterns, and yes, the occasional Hermes tie, should happily coexist in any closet. Choosing a tie from a lesser-known maker, or from a designer that doesn’t produce a pattern by the millions, is preferable as far as I’m concerned since I like my tie to have few brothers roaming the planet, or to be an only child if at all possible. A Matsuda tie from the eighties is one of my favorites, but I get also complimented on my Michele Savoia tie that I believe to be one of a kind. And if a favorite tie is simply too wide to be ever worn under any circumstances (say, if it exceeds 3.5 inches), Tie Crafters in NY will size it down professionally to whatever width you like, breathing new life into your closet for less than the cost of couple of beers.

I’ve always worn khakis, at least since college, that is, when I’d get them from an Army Surplus store near campus that at time still carried real US Army surplus apparel. They were cheaper than any other item of clothing I could buy, were extremely comfortable, and although unfashionable then (in the waning years of hippie culture and well before preppy style), they looked good and, I thought, provided contrast to the sea of flared jeans on everyone under 22. Later, as the supply of well-made army khakis inexplicably dried up, I turned to Bills Khakis, made in Pennsylvania by yes, Bill, who bemoaned the paucity of options when it came to khakis, but unlike me, did something about it by starting a company to make essentially the same pants he had worn in college. Pants that properly sit on the waist, not the hips, and are true to their military origins.

I still love khakis, despite the dreadful tendency towards Casual Friday uniformity—think Steve McQueen and not your sartorially challenged boss—but the soft cotton fabric can be a little chilly in the winter, especially if, like McQueen, you’re prone to hopping on a motorcycle for a spin around town. Enter flannel-lined khakis, and Bills has that covered, too. Years ago I had a pair of his khakis lined in red flannel that survived a cycle spill and a few brutal Northeast winters, but now his are lined in plaids, a nice touch of personality to show off, at the cuff that is.

Socks, like a tie or pocket square, can express one’s individuality no matter the clothes one’s wearing—bespoke suits (believe me, you’re not the only one), or selvedge jeans (again, you and a million other men). Fred Astaire, with his impeccably tailored suits and what can only be described as perfect style, can be seen in classic films wearing bright blue or red socks with an otherwise conservative outfit. Today there are many choices for colorful or patterned socks, but sometimes the old standbys work just fine (or actually better).
Original Rockford red-heeled socks, in continuous production in the US for decades and known as the “sock monkey” socks, now come in a rather nice pink, as well as light blue, and although they work perfectly with jeans, I also wear them with less casual outfits. You can’t, after all, see the heels until you take your shoes off, but they do make a good conversation piece at homes where shoe removal at the door is obligatory. And when they wear a bit thin, yes, you can actually still make an original sock monkey from them, which just might amuse—for a moment at least—a kid being raised on iPads and electronic games.

In the (often faux) retro-crazed first decades of the 21st Century (Mad Men/Banana Republic?), it’s refreshing to look back at true vintage style from the previous century; style we sometimes seem desperate to emulate (Williamsburg, anyone?) Joe Browar (right) and pal strolling down a street in the early fifties look as cool as it gets, and they seem to know it. The haircuts–pomade obligatory–were weekly affairs for a buck or two, the sunglasses were perhaps Raybans or American Opticals, but Joe’s t-shirt is perfection. So is the way he’s wearing it. His high-waisted, deeply pleated pants are definitely not fashionable by today’s exaggerated 1960′s standards, but if you saw this man walking toward you tomorrow, even without the requisite tattoos, would you not think he might be the most stylish person on the street? The pinkie ring only completes the look (hey, Bogie wore one)…

My Persian lamb scarf, actually made in Persia (or Iran for the geographically challenged) from Persian lambs by a tailor on Manouchehri Street in Tehran. Possibly the most elegant fur a man can wear, Persian lamb is also incredibly warm, although anything but a scarf or a collar on a coat might be a going too far , sartorially speaking. Expensive, yes, but if you find yourself in or anywhere east of Persia, say in the ‘stans, you can probably have one made for far less than the cost of a half-way decent cashmere scarf in Europe or the U.S. It’s not Prada, but designing your own is so much more fun.

The airport these days is the only place your socks will be in full view of the public. Wear something nice– bold even– with your loafers. Edward Green shoes from the nineties; a twenty-year old Swaine Adeney & Brigg bridle leather carry on bag and a vintage briefcase. No wheeled luggage, please: looks goofy, and besides, can no one carry even a few pounds anymore?

There are myriad reasons to despise Rick Santorum and his views, and as many reasons to bemoan the sartorial preferences of all the presidential candidates, even Mr. Cool himself, President Obama. But wearing sweater vests, seemingly the mark of a square, a dweeb, or whatever, should not be a reason to poke fun at or demean one of the more extreme politicians of our age. Remember when cardigans, the Mr. Rogers look, were the object of scorn? Today, no hipster worth his Williamsburg digs is without one. Tie bars? Do Brooklynites even know you can wear a tie without a clip? Brogues? Bow Ties? Need I go on? The sweater vest can look square, professorial, or worse. But it can be a damn useful item of clothing, especially if worn under a suit or a jacket, when sweaters with sleeves can add unseemly bulk. This one, in a single ply cashmere is almost twenty years old (from an era when cashmere really came from the throat hairs of the Kashmir goat in the himalayas), woven in Scotland, came from Anderson & Sheppard. Yes, the Saville Row tailors with a famous and infamous client list, clothiers who’ve outfitted everyone stylish from Cary Grant and Fred Astaire to Prince Charles. If it’s good enough for them, it’s good enough for me.