Tailor On The Roof

For 103 years 262 York Street was Headquarters for J. Press until the 2013 Blizzard Nemo literally brought down the roof.

Built in 1860 in faux French Second Empire style, the building originally served as the residence for Cornelius Pierpont, a successful merchant who operated a grocery on New Haven’s Broadway during the 19th century.

The building was purchased by my grandfather in 1910 allowing him to move his tailoring emporium from less salubrious quarters on Chapel Street to a more welcoming presence on the Yale campus across from Saybrook College under the looming steeple of Harkness Tower.

The J. Press store occupied 1800 square feet, but its bespoke nucleus was in the narrow tailor’s quarters in back of the store. Here’s the protocol.

Custom measurements taken by fitters at the stores and road exhibits were promptly sent to Ralph Chieffo, Sr., J. Press chief fitter and designer. Mr. Chieffo (as I always called him well into my middle age) was well known in New Haven for his ability, skill, and knowledge of the custom tailoring trade. When he joined J. Press in 1952, he had over 20 years of experience not only as a skilled tailor; but a designer and cutter, as well as foreman for other firms including Langrock and the Yale Co-op. He was Director of the Chieffo School of Tailoring where he taught custom tailoring, pattern drafting, designing and cutting. His J. Press career lasted thirty years until his retirement and his position immediately filled by son Ralph Chieffo, Jr., who persevered until his retirement twenty years later. J. Press thrived on intergenerational continuity.

After Mr. Chieffo drafted a customer’s measurements onto a paper pattern, Dominic De Petto took over at an adjacent cutting table. Dominic’s career at J. Press lasted nearly a half century. Dominic maintained the extensive woolen library that occupied a large portal on the second floor. He then gathered materials for marking. These included the original garment cloth along with trimmings made up of Hymo canvas, shoulder pads, sewing silk, buttons, lining, linen under-collar, basting cotton, pocket Silesia, sewing silk, open thimble—the whole works. Dominic transported the package to the third-floor tailor shop, home to ten journeyman tailors at their sewing tables. Other bundles were sent in a timely manner around the corner to our second-floor tailor shop above Whitlock’s Bookstore on nearby Broadway. Another dozen bespoke specialists stitched darts, welt pockets, buttonholes, armholes, pressed lapels and fronts. Each garment required approximately 40 hours of labor in those days produced in a swaddling den of cigarette smoke.

This description is but a bare précis of the labor involved. Custom suits further required basted try-ons for the customer back at the store pinning and chalking the skeleton garment followed by two “finished” fittings. Point of sale to delivery averaged six weeks.

The J. Press custom department represented 10% of our dollar clothing volume versus 90% ready-to-wear, but the J. Squeeze custom celebrity transcended its dollar volume.

262 York Street during these COVID times remains an empty lot awaiting rejuvenation. Whatever the venue the ensuing back rooms provide in the oncoming premises, ghostly remnants of a Tailor On The Roof with pins and needles will last forever. 

RICHARD PRESS