Possibly by James Montgomery Flagg for Osborne Co., c. 1940s
The artist signed this pin-up simply “Montgomery.” The signature appears to closely resemble the style of James Montgomery Flagg’s signature. Oftentimes accomplished artists signed their pin-up art more “cryptically” than their mainstream and more famous paintings using just their last name and sometimes even a pseudonym. Contribute in the comments if you can confirm this art was by James Montgomery Flagg or if you know it is another artist with the name Montgomery. Thanks!
Blotto! 