This seems to say (dimly) B N FREEDMAN with something in script lettering below. It turns out this is:
H N FREEDMAN / Skirts
Herman N. Freedman (1873-?) began as a "cloaks" manufacturer on Rivington St. in the mid-1890s. He then moved to Mercer, Greene, Spring, and Prince Sts. in SoHo before arriving at 55 W. 16th St. in 1906. By this time his specialty was skirts. The business re-located to 8 E. 12th St. around 1909. Freedman formed a partnership with Jacob Wolbarst (1881-?) in 1915, and the Freedman-Wolbarst Skirt Co. (at 38 W. 26th St.) stayed in business until 1921/22. Freedman-Wolbarst left a sign at 38 W 26th St.: see 26street3.1.
Herman Freedman appears in both the US Census of 1900 and 1910. In 1910 he is described as "Freedman, Herman M., 38, born Hungary, immigrated 1886, manufacturer skirts." He was living at 915 E. 178th St., Bronx, NY. Living with him were his son Joseph 16, daughters Helen 13 and Marion 9, and a servant Anna Szilogyi 18.
An image in the New York Public Library's Digital Collections dated 1948 shows the H. N. Freedman sign with several others above, including Max Rosenberg & Co. Cloaks Suits Skirts & Waists and Stephano Company Waists & Dresses. Stephano can be found among the signs on the east side of this same building: 16street4.
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