Esphyr Slobodkina spent the first seven years of her life in the small town of Chelyabinsk, a Siberian center of metallurgical industries and the first sizeable station on the Asiatic side of the Trans-Siberian Railroad. Her father, Solomon Aronovich Slobodkin, managed the Chelyabinsk branch of MAZUT, a Rothschild- owned oil enterprise in Russia. Her mother, Itta Agranovich, had been trained as a dressmaker.

Raised by parents of diametrically opposed religious convictions, her father being an unbeliever and her mother coming from a religious Jewish home, Slobodkina received a liberal education and upbringing but was named after the Biblical heroine Esther (Esphyr in Russian).

As part of the family's culturally rich heritage and the generally comfortable, pleasant lifestyle, Esphyr – the youngest of the five Slobodkin children – was taken to the opera, the classical ballet and the theater. The domestic circle also encouraged home-grown and semi-professional talent. Her mother and sister sang beautifully; various aunts and uncles played the piano, wrote and recited poetry, read Pushkin's fairy tales and folk stories to the younger children, and mounted amateur theatricals for the older set and the adults.

Slobodkina was a delicate child who often found herself unable to participate in the stronger children's games, and was frequently confined to bed. During these longish periods of enforced but not entirely unwelcome solitude, Esphyr entertained herself with whatever materials and skills were available. She learned to cut out paper dolls and brought cutting out of doilies into the realm of fine art. During solitary walks, she made an art of arranging wild flowers into elegant bouquets. In a more whimsical vein, she made necklaces and headdresses out of dried berries and acorns and created elegant millinery from rhubarb leaves trimmed with wild flowers

Around the age of ten, Slobodkina saw her first examples of modern art at a large group exhibition in Ufa. Particularly impressed with the paintings on view by the “Father of Russian Futurism”, David Burliuk.These influences would soon surface in some of Slobodkina's first works of art, made after she moved from Vladivostok to Harbin, Manchuria, in Northeast China.

As the political and economic unrest intensified around 1920, Esphyr and Tamara accompanied their mother to the city of Harbin, which at the time was a temporary haven for wealthy refugees from war-torn Russia. Returning to her early training in dressmaking, Mme. Slobodkina soon established herself as a well-liked and respected couturier. From the age of fourteen, the decoratively-inclined Esphyr became increasingly involved with her mother's métier, inventing intriguing details, tying bows, arranging loops and designing embroidery. Her “dreamy designs” were based upon floral and geometric patterns as well as “half-forgotten ancient Russian art or newly discovered treasures of Tutankhamen's tomb.”

Like other modernists in Russia, having grown up with the omnipresent images of ancient Russian icons, Slobodkina developed a lifelong appreciation of their clear, rich colors and flat, stylized forms. She also developed a great liking for traditional Russian peasant arts and crafts. Around 1920, she made her first drawing – “a simple line copy from an Ancient History book of a Greek warrior” which pleased her. This was followed by other attempts to draw, make paper dolls and invent styles for them, or copy dresses from fashion magazines.

In 1922, Esphyr took her entrance exams for the Second Realnoye Oochilische, a junior high school emphasizing mathematics and art in preparation for engineering or architectural careers. Intending to become an architect like her fondly remembered uncle Abrasha, Slobodkina surprised herself by receiving high marks on her art exam. This prompted her first thoughts of a career as an artist.

During her years at this school, she discovered that Mechanical Drawing was not only practical but could be used to create attractive designs:

Drafting gave me tools and gave me sureness of line. With a compass and the aid of colored inks, I could make very beautiful things without knowing how to draw. And that took away some of my uncertainty about my shaky draftsmanship.

Disillusioned with her other courses at the strict Realnoye Oochilische, Slobodkina transferred in 1924 to the more liberal First Harbin Commercial School, where she excelled in a variety of subjects.[16] As a teenager, dreaming of American movie stars and fashions, she enjoyed receiving prizes for the creations she designed for costume balls. The other end of the cultural spectrum of Harbin at that time included the visiting Russian opera, the Moscow ballet, concerts and drama combining experimentation with traditional theater. She also appreciated seeing the highly stylized, angular sets and abstract, geometric costumes of The Cabinet of Dr. Caligari, a landmark modernist film first released in 1920.

Their original desire to enter the Realnoye Oochilishche had made it necessary for Esphyr and her sister Tamara to be proficient in drawing. This led to private studies with the young Impressionist painter Pavel Goost:

The local Bohemian but a terribly nice, gentleman, Mr. Goost was available for a very small fee to teach us the mysteries of real painting. Perhaps he was not a great painter, but he was a pure romantic and a darn good teacher. He didn't just correct or criticize our work, he also talked about the basic principles of all great art in general and in particular… singing rhapsodies to the pearlescent hues of Monet, the purplish hues of Cézanne and the yellows, oranges and warm pinks of Renoir. With Goost's encouragement, Slobodkina painted Park Bench in Harbin in 1927. This small, plein-air painting demonstrates the young artist's command of the broken brushstrokes and bright, modified local colors of Impressionism, along with her understanding of perspective.

Thus, Slobodkina's early work ranged from this rather naturalistic style to the more abstract, stylized, decorative approach of her embroidery designs and Style Moderne fashion drawings. After her brief encounter with Burliuk's Futurist paintings, she became aware of modern art indirectly by looking at the latest fashion magazines with graphic designs often derived from Cubism and geometric abstraction.

Struggling with mathematics, Slobodkina graduated from high school in 1927, still intent upon becoming an architect and an artist. Having learned all that she could from Goost, she decided to leave Harbin and applied for a student visa to the United States. The plan was to join her brother Ronya, who had been living abroad since 1923. Prior to her departure date of January 8, 1928, Slobodkina continued her art lessons and took instruction in the practical trade of millinery, knowing “darn well that no fancy job waited for me in America. Boarding a steamer in Yokohama, Japan, Slobodkina traveled for eleven mostly seasick days across the Pacific Ocean. When she arrived in New York via Vancouver and Chicago, she discovered that Ronya had mistakenly enrolled her in The Greater New York Academy, a free school for missionaries, whose letterhead proclaimed: “A Pathway to a Higher Calling” – a credo just as applicable to her artistic goals. She decided to study English there for a few months during the day. Realizing that she could attend the National Academy of Design for a nominal fee in the evenings, Slobodkina submitted her work in February, 1928, and was promptly accepted:

After having told me that I was an extremely promising young artist on the basis of my slightly modernistic, Art Nouveau work, they kept me in the lowest Antique class, drawing in charcoal from Greek casts, something I hadn't done since I was fourteen, and then proceeded to slowly kill me with boredom for five long years.

She transferred to daytime art classes after the end of her stint with the missionaries, but soon grew discouraged with her teachers' conservative emphasis on slick academic realism in her still life and probationary life drawing classes. The only opportunity “to express a little bit of my natural decorative abilities” was in the composition class of Arthur Sinclair Covey, a painter who created a variety of relatively traditional public murals.

Flat, simplified, outlined figures of ancient Russian peasants in traditional, embroidered, white linen garments are combined with a decorative border. The aged-wood effect of the background with a strong, dark outline was intended as an imitation of the Russian folk art technique of burnt, colored wood. Slobodkina adapted this method from her experiences of working with a crackling process in a parchment lampshade factory.

Her Depression-era work in a millinery factory and in a series of afternoon jobs decorating lampshades, trays, and wastepaper baskets let little spare time for visiting museums, galleries, and reading about art.By 1930, when her mother and sister had emigrated to New York, Slobodkina had to work with them at dressmaking to support the family. Therefore, her friendships with progressive National Academy students like Herbert Ferber were fleeting but memorable. Both young artists were displeased with academic sculpture as taught by Charles Keck. Slobodkina was impressed with Ferber's outspoken attempts to create stylized, modernistic sculpture, which prompted his dismissal from the academy in 1930.[30] Spending time in the school library and beginning “to look sideways at Brancusis and Archipenkos”, Slobodkina saw some examples of their work and that of other modern artists in magazines.Her favorite publications were Art News and Jar Ptitza (Firebird), a Russian Review of Art and Literature. Published abroad from 1921 to 1926, Jar Ptitza contained many color illustrations of a variety of traditional and modern Russian decorative and fine arts.

In 1931, Slobodkina met a Russian student who would soon play an important role in her life and art. Older than she by one year, Ilya Bolotowsky had already achieved some prominence at the Academy with his old master-influenced paintings. Also “among the better compositions, usually with an honorable mention, his work could be found on the exhibition board of the composition class.

Similarly disillusioned with the National Academy's conservatism, the intelligent, loquacious Bolotowsky spent a year traveling around Europe and sending “very educational postcards about Cimabue, Giotto and other great masters” to his new friend. When he returned in October 1932, armed with reproductions of masterpieces and determined “to marry one of the Slobodkina girls”, Esphyr saw her opportunity. Eager to learn from “this walking encyclopedia”, she became an avid listener, if a reluctant girlfriend.

I was nearly twenty-four. The four years at the Academy produced nothing but frustration and actual retardation in my efforts to become a serious artist. One day, watching me perform some clever domestic artistry, Ilya remarked dryly… “At this rate, if you don't watch out, you may end up spending your entire life making pretty cushions for your living room.”… I… candidly admitted to him that the only reason I spent so much time on the cushions was that I did not know how to go about learning to paint.

Accustomed to being asked for his advice, the omniscient Bolotowsky launched into a lecture on composition, profusely illustrated with examples from the past and present. By the time of their next meeting, Slobodkina had a surprise for him, the skillfully composed Still Life with Banana The somewhat Expressionist distortions and brooding quality of this painting suggest Slobodkina's absorption and adaptation of ideas discussed at social gatherings with Bolotowsky and his friends, particularly Byron Browne and Giorgio Cavallon

Ilya painted his own expressive portraits of Esphyr in a style reminiscent of Picasso's Rose period and also took her to see a variety of old master and contemporary art exhibitions during the winter and spring of 1933.
Slobodkina's moody portrait sketch of Bolotowsky was painted during the summer of 1933, when she was still vacillating between the Impressionist theories of her early training and Ilya's modern, Expressionist views. At this time, he finally persuaded his reluctant girlfriend that marriage would provide her with American citizenship and enable her to quit the dreaded National Academy. They were married during a productive vacation on a farm near High Bridge, New Jersey. Back in New York, Slobodkina continued her slow progress, impeded by the constant burden of housework and a demanding husband. The Bolotowskys spent the summer of 1934 in Noank, a small seaside village at Mystic Harbor, Connecticut. Overwhelmed by the combination of chores and intense sun, Esphyr did not paint on the nearby Mystic Island. She chose instead to paint the local landscape, barns, shipyards, and gasoline stations. In Road to Mystic, Connecticut, she developed Expressionist distortions by translating forms into crudely rendered, simplified, flat, color planes, suggesting the impact of Bolotowsky's work.

Painted in an entirely different style, a more somberly colored still life of buttercups on a table seen from above, prompted the following praise from Bolotowsky, which was, incidentally, his final comment on her work:Almost as good as [Yasuo] Kuniyoshi. Not bad. Not bad at all. Now you can call yourself an artist.During the fall of 1934, the couple stayed at Yaddo, the artists' colony in Saratoga Springs, New York.Slobodkina painted a variety of Expressionist still lifes and interiors, while Bolotowsky worked on “slightly abstracted, heavily stylized scenes of the nearby Yaddo structures, and street scenes.”[42] Although her style was still externally close to his, she was relying less on her husband as “a mentor in all things artistic”.

Sometime after their return to New York, Ilya was offered an unusual employment opportunity to work at “an interesting new firm experimenting with a secret, revolutionary process of textile printing.” Because he had worked earlier in a batik studio, Bolotowsky preferred to secure employment with the Public Works of Art Project, which provided him with a small but steady income and time to paint. He and other family members turned the offer down, paving the way for Slobodkina to develop a new career as a textile designer, using her talents for high style, ornamental design and firm, well-balanced compositions. As a supervisor at a subsidiary plant of the Cretona Print & Dye Works in Clifton, New Jersey, she became an expert at the unique polychrome process of simultaneously printing an unlimited number of incredibly refined, stylized color patterns on silk.

During the course of her brief employment before the plant closed down, Slobodkina lived with her family in a cramped apartment in Clifton and visited her husband on the weekends. Left alone one weekend, she created her first Cubist-inspired painting, The Sink:

I had been silently gathering information about Cubist theories and…promptly produced a fractured image of the sink in the Clifton bathroom. It was quite a breakthrough for me, all on my own. Ilya never took to Cubism in its pure form.

Aware of Bolotowsky's previous, occasional experiments with Cubism, she was scornful of his seeming preoccupation with “imitating the latest style of his latest idol… Picasso. Preferring to learn from “the works of lesser masters”, she was fascinated by the flat, clearly defined, interlocking color planes in the multiperspectival paintings of Juan Gris – “a slave to the Cubist theory, his reasoning very easy to follow.”[48] She was, however, also very interested in the more free-form Synthetic Cubist still lifes of the 1920s and 1930s by Picasso and Braque.[49] Their possible influence is suggested by the transitional, semi-abstract Tools of the Trade .The artist has selected and stylized the compelling forms of such studio elements as a saw, mortar and pestle, arranging them in semi-cubist overlapping planes.

Slobodkina's growing interest in Synthetic Cubism was possibly nurtured not only by reproductions but by occasional visits to A.E. Gallatin's Gallery of Living Art at New York University. There she would have seen an ongoing selection of work by Picasso, Braque, Gris and Léger.[50] She was also aware of Cubist and abstract art created by Byron Browne, Gertrude and Balcomb Greene and other colleagues in the Artists' Union, which she had joined earlier in 1934

Regarding this first trade union for artists as a very important part of her life, Slobodkina participated in strikes and sit-ins to expand employment opportunities for artists and secure Government patronage for the arts during the Depression. Slobodkina also exhibited her work in some of the group's exhibitions, which were subject to mutual criticism after the official opening.[52] She has recalled that the early shows included work by such relatively renowned artists as Arshile Gorky and, more important, Stuart Davis, whose work she has usually appreciated as being “in good taste.”

While Davis' paintings may have been indirectly encouraging for her experiments with Cubism, she truly appreciated the lighter, more social side of the Artists' Union as well. With her decorative flair, Slobodkina contributed various posters, banners and wall decorations for several fund­raising events. Her humorous sketches of The Latest Styles for Unemployed Men and Women were probably designs for costumes or decorative drawings for the Mad Arts Ball. Attending this gala affair, billed as “a costume ball kidding the ads”, Slobodkina herself wore a striking black satin dress decorated with a reproduction of the Artists' Union emblem (a militantly raised fist grasping paintbrushes
By the summer of 1935, she was experimenting “with the gradually freer interpretation of Cubist theory”, while Bolotowsky was painting pure, geometric abstractions influenced by Malevich's Suprematism.[55] Their marriage, however, was not going well. After an experimental break-up, he sheepishly returned to Slobodkina. She accepted him, but on her own terms: separate residences and no more domestic duties. With this arrangement, Slobodkina finally gained the freedom to focus more on her own work. Thus, the following years would prove to be a key period in her developing career.