Triumphing Over Time: Lasting Elements of Classic Style

By Tony Ventresca

What are the lasting elements of classic style? For most people, it’s probably a long list and definitions will vary from person to person. My definition is the following: clothing elements which have remained more or less unchanged in design and function for at least 50 years and which have never been irreversibly altered by fashion designers and retailers. Everyone will have their own list—this is mine.

Double-Breasted Suits

Double-breasted men’s suits have been around for two or three centuries, depending on your definition of “suit”, but the recognizably modern version appeared in the 1930s with the rise to primacy of Savile Row tailoring. The modern version has balanced proportions, long(ish) peaked lapels, buttons on the waistline, and a fitted silhouette (the vests have disappeared). Deviations in the 1960s and 1980s were short-lived and did not impact the classic design. Go to a good tailor today and he will make you a double-breasted suit that has not changed in eighty years.

Single-Breasted Sports Jackets

Easy to overlook, but indispensable. First appearing in the 1920s, the earliest versions were truly “odd jackets”, distinguished both in details and application from suits. Belts, pleats, and lots of buttons were the order of the day. In the 1930s, simplified versions resembling suit jackets became more popular and the early Norfolk jacket versions largely disappeared from men’s wardrobes. Whenever a business suit is too formal and a blazer is too flashy, the sports jacket has always been the go-to garment. With the advent of “business casual” Fridays in the 1990s, the future of the sports jacket was assured and twenty years later these garments have almost achieved on-par status with suits among businessmen.

Long Neckties

The word “necktie” was first used in the 1930s to describe cravats worn once around neck and tied in bow or knot. This definition more or less describes the modern necktie, but in those days neckties were shorter and wider things intended to be tucked under waistcoats. Today, neckties are longer, narrower and worn beneath fold-down shirt collars. The modern necktie might point at your genitals, but that’s not why it’s there (and one wonders about people who come up with such ideas). Forget fashion and rules, and buy neckties which express your personality and match the width of your suit lapels.

Button-Down Collars

Brooks Brothers calls it a “polo collar”, although so far no one has found photographic evidence of it actually being worn by polo players—most wearers are more likely to be playing the markets and riding minivans than playing polo and riding ponies. So is the name a marketing fantasy? Probably. Is the design a classic? Absolutely. Why? There simply exists no other shirt collar as casually charming, or as widely acceptable, as the button-down. It can be worn with a suit or shorts, in church or at a barbecue, by the young and the old. It’s been copied many times, but it has always stayed the same.


Not much can be said about trenchcoats that hasn’t already been said, but it’s worth noting the first ones were made from a tightly woven wool gabardine, not the cotton gabardine which predominates today. The cloth was created by Thomas Burberry in the 1870s, and the iconic garment itself was designed just in time to keep a generation of doomed young men warm and dry in the First World War. Officers may have started out wearing trenchcoats, but in the Second World War these practical garments enjoyed a more egalitarian role, since other ranks had access to them in the US Army, depending on branch of service. Designers and retailers have often made them shorter or longer, fancier or plainer, but the basic design has survived intact for almost a century.


Cotton twill fabric of combed yarns made into men’s trousers of traditional design. Unquestionably the most versatile pants ever created. You can wear them with sports jackets, leather jackets, and nylon jackets; you can wear them with dress shirts, polo shirts, and tank-tops; you can wear them with cap-toes, loafers, and sneakers. These irreplaceable garments started out as (nearly) unwanted goods: woven in Manchester, exported to China, and re-sold—dumped, one suspects—to the American army occupying the Philippines just before World War II. So we owe a debt to some opportunistic Chinese dry goods broker for the most versatile pants in the modern wardrobe; six decades old and more popular every year.

Grey Flannel Pants

The second most versatile pants in the modern wardrobe. First appearing in the 1920s as summer resort pants (in white), by the 1940s the grey version became so popular they were worn year-round for casual wear. Old photos reveal that grey flannel pants had at one time a presence of their own, grabbing the eye even when paired with a windowpane sports jacket or blazer with gold buttons. This was probably due to a dry surface, fuzzy nap, heavy weight, and plenty of drape. Today’s versions, by contrast, are made of harder, wetter, and thinner materials and can easily seem to be style afterthoughts with little presence of their own. Hunt out the real thing, it’s worth the effort.

Leather-Soled Dress Shoes

It’s hard to pin down the most classic style of oxford shoes, but the plain cap-toe and standard full-brogue must be the leading candidates. Conservative Britons consider the cap-toe to be the businessman’s standard shoe, but in America the wingtip is often preferred. According to style historians, oxfords became popular in Britain in the late 1800s (at Oxford), spreading gradually throughout Europe and to the United States, and by 1910 most men wore them most of the time. Interestingly the Russians embraced the oxford early: in a country under snow for eight months of the year and mud during the rest, oxfords became the mark of the urban resident and boots the peasant or labourer, while in the rest of Europe—Britain in particular—tall boots were the sign of the horse-riding elites.

Boat Shoes

Everyone knows the story about the dog, the penknife, and the yachtsman, so I won’t repeat it here. One thing needs to be mentioned: although Paul Sperry introduced his “siped” rubber soles in 1935, his original boat shoe was a lace-up canvas oxford, not today’s oiled-leather moccasin. But it’s the moccasin version which has proven one of the most bulletproof and classic shoe designs of all time. Pink, red, and baby-blue versions aside, no one has managed to fatally alter the classic design—even the copycats and counterfeiters serve up the genuine style.


Alan Flusser, Style And The Man (New York: HarperCollins, 1996).

Alan Flusser, Dressing The Man (New York: HarperCollins, 2002).

Karlen & Sulavik, The Indispensable Guide To Classic Men’s Clothing (New York: Tatra Press, 1999).

Paul Keers, A Gentleman’s Wardrobe (New York: Harmony Books, 1987).

Oscar Linius, A Well-Dressed Gentleman’s Pocket Guide (London, Carleton Publishing Group, 1998).

Mary Brooks Picken, A Dictionary Of Costume And Fashion (originally New York: Funk & Wagnell, 1957; this edition Toronto: Dover, 1999).

Bernhard Roetzel, Gentleman (Cologne: Konemann, 1999).

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