She was reportedly described by The New York Times as being the highest-paid woman artist in the United States, though she lived in comparative poverty in later years.

[4] During her early childhood years, Dryden showed unusual artistic ability, designing and selling clothes for paper dolls.

Her artistic education consisted of four years of training in landscape painting under Hugh Breckinridge and one summer school session at the Pennsylvania Academy of Fine Arts.

[5] Her "essentially romantic style produced some of the most appealing, yet fantastical images on Vogue covers, frequently depicting imagined rather than realistic representations of dress.

[6] This was Dryden’s "most prolific working period" and her inspiration is also often associated with the start of Art Deco" with "has graceful, feminine forms" showing "whimsical, imaginative, and notably decorative illustrations of full figures.

"[7] Dryden stopped working for Vogue in mid-1923 and began designing wallpaper patterns and illustrated advertisements for companies making dress fabrics, towels, and hats.

[4] In the late 1920s, Dryden designed the covers for the fashion and dressmaking magazine The Delineator characterized by streamlined cubist forms as a "reflection of modernity and industry.

Christopher Gray wrote, "The 1925 census recorded her living at 9 East 10th Street with her 25-year-old Philippine-born cook and butler, Ricardo Lampitok."

[16] Studebaker described the interior of the 1937 cars as "refreshingly ventilated and generously roomy, …tastefully and distinctively styled by famous Helen Dryden, America's "first lady" of design.