Chipp
American Clothing Manufacturer, New York, Founded 1947
Sidney Winston founded Chipp in 1947 following many years with J. Press, where he began working after high school. Previously located near 44th and Madison — among the cluster of traditional clothiers Brooks Brothers, J. Press and Paul Stuart — Chipp at its peak employed 30 tailors and a sales force of 10, and offered both custom and ready-to-wear clothing.
Paul Winston began working for his father Sidney’s New York-based clothing company Chipp in 1961. Vivid linings are just one of the signature styles of Winston, Chipp soon became renowned for inventing the patching of madras and tweed, and for dressing President Kennedy. Chipp was was the definitive source of John F. Kennedy’s "Ivy League" wardrobe and became his primary tailor during his presidency. JFK was introduced to the shop in 1958 by his brother-in-law, actor Peter Lawford, who was already a loyal client. During his presidency, Sidney and his son Paul Winston would visit the White House or conduct bespoke fittings at JFK’s private apartment in the Carlyle Hotel.
While Brooks Brothers is often publicly associated with the "Ivy League" look, it was Chip who crafted the bespoke suits that defined JFK's presidential image. Before this, Kennedy wore ready-to-wear suits (often from Brooks Brothers) that didn't fit his frame perfectly. The switch to Chipp marked a transition to custom, bespoke tailoring that accommodated his specific physical needs, including his back brace.
While Chipp was famous for the bold, "Go-to-Hell" prep aesthetic—think patchwork madras and embroidered critters—they pivoted to a strictly conservative approach for JFK. Instead, they created impeccably tailored power suits that defined the New Frontier.
One of the President’s most iconic looks, the grey chalk-stripe suit seen in countless historic photos, was a signature Chipp creation. By moving away from the boxy, shapeless "sack suits" of the 1950s, Chipp’s tailors crafted a slimmer, more athletic silhouette that modernized the presidential image and cemented Kennedy as a permanent style icon.
Paul Winston began working for his father Sidney’s New York-based clothing company Chipp in 1961. Vivid linings are just one of the signature styles of Winston, Chipp soon became renowned for inventing the patching of madras and tweed, and for dressing President Kennedy. Chipp was was the definitive source of John F. Kennedy’s "Ivy League" wardrobe and became his primary tailor during his presidency. JFK was introduced to the shop in 1958 by his brother-in-law, actor Peter Lawford, who was already a loyal client. During his presidency, Sidney and his son Paul Winston would visit the White House or conduct bespoke fittings at JFK’s private apartment in the Carlyle Hotel.
While Brooks Brothers is often publicly associated with the "Ivy League" look, it was Chip who crafted the bespoke suits that defined JFK's presidential image. Before this, Kennedy wore ready-to-wear suits (often from Brooks Brothers) that didn't fit his frame perfectly. The switch to Chipp marked a transition to custom, bespoke tailoring that accommodated his specific physical needs, including his back brace.
While Chipp was famous for the bold, "Go-to-Hell" prep aesthetic—think patchwork madras and embroidered critters—they pivoted to a strictly conservative approach for JFK. Instead, they created impeccably tailored power suits that defined the New Frontier.
One of the President’s most iconic looks, the grey chalk-stripe suit seen in countless historic photos, was a signature Chipp creation. By moving away from the boxy, shapeless "sack suits" of the 1950s, Chipp’s tailors crafted a slimmer, more athletic silhouette that modernized the presidential image and cemented Kennedy as a permanent style icon.