Having received training at the Art Institute of Chicago and the Art Students League of New York and having studied with artists in Munich and Paris, she adopted a variety of styles, ranging from representative to highly abstract, and worked in a variety of media including oil on canvas, oil on heavy coated paper, watercolor and ink on paper, and monotype printing.

[7] During her first year, she was photographed for an article in the Chicago Tribune wearing an extravagant gown and beating an oversize bass drum in a "Mardi Gras" fundraiser for the school.

[8] In 1909, the school awarded her a $500 travelling scholarship for which Chicago women artists were eligible and in her final year she won a prize for composition.

[6][11][12] Some time after her return to Chicago in 1913, she moved to Manhattan where she lived in Greenwich Village and worked with the Tonalist painter, Birge Harrison at the Art Students League.

[1][15] In 1909, while she was studying at the Art Institute of Chicago, Loeb was one of five students selected to paint murals for a new school, Lane Tech, on the city's near north side.

Commissioned by the philanthropist, Kate Sturges Buckingham, the murals depicted advances in technology from earliest times.

In 1910, Loeb received another mural commission, this one from a public elementary school named after furniture store owner, John M. Smyth.

[6] She joined the Federal Art Project in the late 1930s and in 1937 painted a mural for the public library in Falmouth, Massachusetts.

[19] In reviewing the next year's show, a critic for the Chicago Tribune said Loeb's portrait work stood out "strikingly".

In a 1932 review of Loeb's solo exhibition in the Walden-Palmolive Gallery, Eleanor Jewett said that the abstract paintings she saw were "naive, primitive conceptions" that were "dull, stiff, and lifeless".

The author said, "[I]n Boston in the 1930s, artists did not have to even suggest the radicalism of Brancusi ('egg-shaped sculpture') or the Cubists ('angular figures with purple faces') to be classified as 'modern' and banned from most clubs and exhibition opportunities.

Slight abstraction or unusual color, such as was found in the work of Dorothy Loeb, was scorned as crude and defiant and generally perceived to be too avant-garde for the Copley Society or the Guild of Boston Artists.

Commenting on the Loeb-Lazzell duo exhibit of 2002 in Provincetown, a critic for the Cape Cod Times called Loeb's paintings looser than Lazzell's and said they were more fanciful.

[6] An example of Loeb's fanciful and freely drawn style can be seen in the undated watercolor, "Fantasy Flight", shown above, Image no.

In 2021, an article in the Provincetown Independent gave a relatively extensive consideration of works on long-term display in a local nursing care facility.

The author described a watercolor called "Flower" as "a colorful, semi-abstracted" painting in which the observer "can see dry brushstrokes" in some areas and, in others, "watery blues, greens, reds, and yellows mingled together."

[13] Loeb began her teaching career in the years before the outbreak of World War I as an instructor for Hull House, the settlement on the near west side of Chicago, and in 1923 organized an exhibit of her students' work.

The young artists could choose their own media and subjects and employ whatever technique they wished in planning and executing their works.

[30] In 1930, she began teaching classes in an experimental education program at PS 41, a public elementary school in the Greenwich Village section of Manhattan.

Discussing her methods, Loeb told an interviewer, "the youngsters developed in the regular channels of public school instruction become somewhat self-conscious and inhibited in expressing their feelings and impressions about their experiences, and of course work less freely than these children have done.

Using photojournalism and focusing largely on contemporary celebrities, the magazine was an unsuccessful attempt to establish a progressive alternative to Life.