Chipp Neckwear celebrates the Preppy “Go-to-Hell” Look

In the heyday of the Ivy League look – that golden era between This Side of Paradise (1920) and The Official Preppy Handbook (1980) – a group of legendary menswear shops clustered in midtown Manhattan around Madison Avenue and 44th Street. The big four – Brooks Brothers, J. Press, Paul Stuart, and Chipp – catered to the American upper class, chronicled in the works of sociologist E. Digby Baltzell, who popularized the acronym WASP. While the style these clothiers cultivated is distinctly traditional and conservative – 3/2 roll blazers, Oxford cloth button down shirts, repp ties, and so on – WASPs also developed a playful and irreverent side, known as the preppy “Go-to-Hell” look. This look got a big boost from fashionable resorts – from the salmon-colored Nantucket Reds sold at Murray’s Toggery Shop, to the wild tropical prints in hot pink and lime green from Lilly Pulitzer. But the WASP gentleman did not need to be on vacation to express his sense of humor. The traditional clothiers of New York City offered plenty of options for “fun” clothing. Perhaps the most fun-loving clothier of all was the late great Chipp.

Chipp Clothiers was established by Sidney Winston in 1945. Sidney had previously worked for J. Press as a travelling salesman for the New England boarding school trunk show circuit. His business partner, Lou Praeger, had also worked for J. Press as the manager of the Princeton store. Chipp offered both custom and ready-to-wear clothing and served an impressive roster of clients including President John F. Kennedy, Secretary of State Cyrus Vance, IBM executives Tom and Arthur Watson, actor Peter Lawford, and basketball player Wilt Chamberlain.

While the original Chipp closed shop in the early 1980s, the legacy of the brand lives on in Chipp Neckwear, a clothing brand founded by Sidney’s son, Paul Winston. Chipp Neckwear offers neckties, suspenders, and watches in a wide variety of patterns for individual customers and patterns for clubs, schools, and organizations. According to the company’s website:

Chipp Neckwear is dedicated to upholding the legacy of bold style, innovative design, and distinctive humor that has been synonymous with the Chipp brand since Winston’s father established the family business and the “Go-to-Hell” look in 1945…The company was responsible for popularizing the preppy clothing canon with innovations like patch madras pants and embroidered corduroys.

Paul Winston, now 85, attended Hopkins School in New Haven, Connecticut and Union College in Schenectady, New York. After joining the family business in 1960, he commuted by train from Stamford to New York for 37 years. Chipp served as the tailor to President Kennedy and other members of the Kennedy family, including Bobby Kennedy. Paul thoroughly enjoys working in the clothing business because he enjoys meeting people. He is full of great stories and loves to talk (he welcomes phone calls at 203-559-7653). For him, running Chipp Neckwear is a labor of love. Paul has the sharp wit of a comedian but admits that his sense of humor is not always shared by others. Even his own wife tells him – “Paul, that is not in good taste.” For Paul, that is exactly the point – preserving the legacy of the “Go-to-Hell” Look. One of the best articles on this topic is Damned Dapper: The Preppy “Go-to-Hell” Look written in 2010 by Ivy Style founder Christian Chensvold. The article mentions Chipp and Paul Winston:

Paul Winston says it wouldn’t surprise him if his father Sidney invented embroidered pants…Chipp is also the company most credited with the patching of madras, seersucker and tweed, which began when Sidney Winston got the idea of using leftover scraps of fabric, sewing them together like a quilt, and making trousers and jackets from it. Patching soon became one of Chipp’s trademarks, though not in the literal sense: Winston has reaped no royalties from mainstream retailers’ many patch-madras offerings the past few seasons.

The Official Preppy Handbook mentions “Specific Color Blindness” which makes certain irreverent color combinations not only socially acceptable, but desirable:

Primary colors and brilliant pastels are worn indiscriminately by men and women alike, and in preposterous combinations. In some subcultures, hot pink on men might be considered a little peculiar; Preppies take it for granted. (The Official Preppy Handbook 1980, p. 122)

Chensvold writes:

The whole point is to have an insular code, says Birnbach. “Whether it’s slang or clothing, it’s a way to identify one another in one’s group — and many of these Old Guard, WASPy types weren’t particularly interested in knowing people from another group.” (Chensvold 2010)

The “Go-To-Hell” Look is a continuation of this theme. On the surface it may seem radical and rebellious, yet in reality it is an emblem of class cohesion and preppy solidarity. According to The Official Preppy Handbook:

In casual wear it is considered very spirited, very fun-loving to wear one offbeat loud item…Only one item of clothing may be this way, however. The total outfit must be traditional – the usual uniform – with this one exception…Being fun-loving should never be confused with being nonconformist. (The Official Preppy Handbook 1980, p. 193)

Paul Winston understands that clothing is about catering to wants, not just needs. Through Chipp Neckwear, he offers products that diverge just a little from the conventional and that resonate with those who appreciate traditional craftsmanship and are not afraid to make a statement.