[2] In 1923, he purchased the lease and contents of a small clothing store at Seventh Avenue and 17th Street in Manhattan selling his wife's wedding ring to finance the transaction.
[3][2] As his store was located in a non-traditional retail area, Pressman purchased inventory at a discount at bankruptcies, auctions, and in odd lots[2] including searching the newspapers for notices of death and divorce among the city's elite.
[2] His success incurred the wrath of the manufacturers who pressured local suppliers to limit sales to Pressman; Pressman circumvented their efforts and started to purchase excess inventory from independent retailers in the South, where the New York manufacturers had less influence.
[2] Pressman was known for aggressive sales promotions including "No Bunk, No Junk, No Imitation" and "Calling all men to Barneys" (mimicking Dick Tracy) as well as the heavy use of radio advertising to attract customers to his out-of-the-way location.
[5] In the 1960s, his son Fred changed the focus of the business and starting advertising to customers who were not as price sensitive and began to carry expensive suits and coats.