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Take A Good Look Down, Classic Footwear

Originally Posted: October 30, 2009

Douglas MacKaye Harrington

The Cap-Toe shoe is a classic Oxford with an overlapped toe. Images courtesy of Brook Brothers

Southampton - I'll admit it, with the exception of a very formal event, most of us guys can make it through an entire Hamptons summer in the same pair of Sperry Topsiders. These classic boat shoes are proper with a blazer and a pair of jeans or chinos and a polo or Oxford shirt at most casual summer fetes. It also goes without saying that most of us do not even pack socks in our weekend travel bags. However, the cooler weather presents different opportunities so put those well-worn leather summer loves away and let's consider some classic options for autumn and winter footwear.

As noted in previous columns, I am a traditionalist. At 56 years old, I am not about to pretend I am a hip barometer of what the twenty-somethings should be wearing. I perhaps see myself as a fashion historian, recording for those twenty-somethings some classic fashion styles for further reference that have never gone out of style and, frankly, never will. They may not be appropriate for you today, but one day, when you decide to define your own personal style at say the ripe old age of 35, you may decide that some of these classic options are perfect for your permanent, personal fashion de rigueur.

Wing-Tip is a favorite classic shoe.

Like it or not, fashion has changed little in the last 100 years, particularly men's fashion. Yes, we guys go back and forth in decades between two-button and three-button suits, and the double-breasted occasionally finds its way back into style, sometimes four-button, sometimes two-button. Herringbone finds its way back into favor, as does silk over wool, as will tweed over checkered and narrow legs over billow, as does a narrow lapel over a wide. Ties narrow and widen like celebrities on a Jenny Craig diet, and I think maybe are based on the seasonal personal weight of Calvin Klein, Ralph Lauren, or the definitive tie/shirt god Thomas Pink. A wide tie makes you thinner and a thin tie wider. We have little room for innovation; let's face it, as men we basically wear pants, shirts, coats, suits and, yes, shoes. Of course I am a Scot and yes I do own a kilt, but we will save that for another column.

I have no intention of addressing the issue of sneakers except to say that in my option they are appropriate for the gym, jogging and yard work. They are not appropriate with a suit or even, in my opinion, a pair of chinos and a blazer. Okay, if you want to look like a male RN fresh off work, go ahead. It certainly is not my choice. Okay, now that it has been said, let's talk classic leather footwear.

Some of us actually kept a penny (or dime) in these Penny Loafers.

Let's start with the concept of the basic, modern formal shoe which I believe can be defined as the Oxford. Essentially two pieces of leather, the stay and the toe, stitched together with a no seam toe and contoured to be adhered, usually stitched, to a thicker piece of leather known as the sole, which also has the element of a heel. Generally there are five eyelets for laces to adjust the fit, but there can be as many as six and as few as four. Sometimes Oxfords are called Bucks, particularly when they are made from suede, as in the case of the traditional summer white Bucks occasionally seen in the Hamptons as the perfect accompaniment to a white linen suit or chinos with a blue blazer.

My favorite shoe is the basic Cap-Toe. This is a classic Oxford with an overlapped toe, usually defined with a thin layered strip of added leather, but sometimes simply stitched. Generally the overlapped top will be of a thicker density, in its very utilitarian original intention, but now it is mostly cosmetic to simply define the traditional style. The strip can be plain or ornamented with an imprinted design, which then defines it as a Perforated Cap-Toe. The toe can further be imprinted with an added elaborate design that is defined by Brooks Brothers as a Medallion Perforated Cap-Toe, and who am I to argue with Brooks Brothers.

If the strip across the front is cut in a curved winged design it is called a Wing-Tip and is its own separate piece stitched to the upper. It is more often than not elaborately perforated with a design, but not always. The winged toe strip usually extends from the front of the shoe to the middle of the upper on each side before disappearing into the sole. These are classic Wall Street shoes and like the Cap-Toe are generally found in black, brown, saddle or cordovan colors. Sometimes a Wing-Tip can be multicolored with toe, stay and lace area in black and the upper in white for example. I wouldn't wear these to the office, but they are a must if you happen to be cast in a production of "Guys and Dolls."

The tasseled loafer has always been popular.

Split-Toe shoes are not perforated with designs, but have a split seam in the front of the toe and a curved seam that wraps around the top of the toe and extends on each side across the top to the lace area. Perfectly proper for work, but I think less classy in appearance than the Cap-Toe or Wing-Tip. In the case of all these shoes the toe is generally curved, when it is not it is appropriately called a Square or Squared-Toe version.

Shoes without laces are generally considered Slip-Ons or Loafers and can be plain and simple in design like a moccasin, or ornamented with an upper strip as is the case with the Penny Loafer. Yes, you can actually slip a penny into the strip, but in the days prior to cellular I put dimes in them in case I needed to make a call on a pay phone. Today it would not work, as quarters are simply two large. A particular favorite of mine in the Slip-On style of shoe is the Tassel or Tasseled-Loafer. Hard to describe in words, but essentially where the strip or laces might be there are two dangling tassels. These are both perfect for work with a suit or in a casual setting. Again Slip-Ons can be both curved or square toed and can be found in both leather and suede, even alligator or lizard I suppose.

Although it is more and more common to find soles and heels made from synthetic materials, often more durable than leather, do not buy a pair of shoes with synthetic uppers. Frankly, in my opinion, it is like wearing a polyester suit. Something I hope never rears it ugly head again in the rolling waves of seasonal fashion.

Every gentlemen should own a pair of tuxedo shoes.

Finally, if you own a tuxedo, and any true gentleman should, buy a pair of true tuxedo shoes, in either a Slip-On or more appropriately Oxford design. They should be constructed of shiny, almost reflective patent leather with a very thin soul and low heel and, like the tuxedo itself, should only be black.

Of course there are many other designs of footwear, like boots, cowboy, work and English, as there are numerous variations of sandals, but what I have described to you here is the classic line-up of footwear. Spend big at a reputable store like Brooks Brothers, Florsheim or Cole Haan for example. Well crafted shoes will cost $150 or more, but if you keep the uppers polished and in good condition and replace the soles and heels as needed they will last you a decade. Think of it as an investment in classic, tasteful footwear that will never go out of style because, frankly, it won't!

Frequently mistaken for the "Most Interesting Man in the World" from the Dos Equis commercials and the iconic gray-bearded Sean Connery, DMH is the Senior Contributing Editor at Hamptons.com. www.hamptons.com Hamptons HamptonsOnline HamptonsOnline

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