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How the Flapper Took Over Chicago: A Look at the Chicago Beauties of the 1920s

The 1920s in Chicago, as in the rest of America, saw the rise of a new image for women. This was the era of the “flapper,” a style that broke away from the restrictive fashions of the past and embraced a more modern, liberated look. This new standard of beauty was celebrated in newspapers, on stages, and in the city’s newly established beauty contests.

The Flapper Silhouette and Style

The defining look of a 1920s Chicago beauty was the flapper silhouette. This style favored a straight, boyish figure over the curvy shape that was popular in previous decades. Dresses were designed with a drop waist, where the waistline of the garment sat at the hips rather than the natural waist, which de-emphasized curves and created a long, lean line. Hemlines rose significantly, reaching the knee by the middle of the decade, which allowed for greater freedom of movement for dancing styles like the Charleston.

Hair was a critical element of the look. The most fashionable style was the bob, a short haircut that could be worn straight, with waves, or in a tight, shingle cut at the nape of the neck. This short hair was often worn with a cloche hat, a close-fitting, bell-shaped hat that was pulled down low over the eyebrows. This style framed the face and drew attention to the eyes.

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A New Face for a New Era

The popular makeup style of the 1920s was dramatic and distinct. Eyebrows were plucked thin and penciled in, often in a downward-curving arch. Eyes were heavily lined with dark kohl eyeliner to create a smoky, dramatic look. A key element was the “cupid’s bow” lip, where lipstick, typically in shades of deep red or maroon, was applied to create a small, sharp heart shape, emphasizing the peaks of the upper lip and the center of the lower lip. Pale, powdered skin provided a stark contrast to these dark eyes and lips.

The Rise of the Beauty Pageant

This new standard of beauty was put on public display in bathing beauty contests, which grew in popularity throughout the decade. Chicago launched its own Miss Chicago pageant in 1922, just one year after the first Miss America contest was held. These events provided a platform for young women to be recognized for their appearance and poise.

The swimsuits worn in these competitions were a key part of the modern look. They were a significant departure from the cumbersome, full-coverage bathing costumes of the past. Made of wool jersey, these one-piece suits were more form-fitting and allowed for more of the arms and legs to be exposed. They were still modest by today’s standards, but in the 1920s, they represented a bold step toward greater freedom in women’s swimwear. These contests, held in a bustling and modern city like Chicago, celebrated a new ideal of American beauty that was active, youthful, and independent.

#1 Miss Chicago Georgia Theodora Hale, from Englewood, won the first Miss Chicago contest in 1922 and became a silent movie star, with a notable role in Charlie Chaplin’s “The Gold Rush” and as Myrtle Wilson in the first film adaptation of “The Great Gatsby” in 1926.

#2 Miss Chicago Margaret Leigh came in fourth place at the Atlantic City Miss America beauty contest in 1924.

#3 Miss Milwaukee Clare Koehler, Miss Chicago Margaret Leigh, Miss Los Angeles Lillian Knight, and Miss Sioux City Alta Sterling at the Atlantic City Miss America beauty pageant, 1924.

#4 Miss Chicago of 1925, Margarita Gonzales, was a candidate for the national title at the Atlantic City beauty contest in 1925 but was eliminated in the first round.

#5 Cars covered in flowers for a Chrysler Parade to honor beauty queens, 1926.

#6 Mae Greene, 18, was chosen as Miss Chicago 1926 out of 4,000 rivals and went on to represent Chicago at the Atlantic City Miss America beauty pageant, 1926.

#8 Margaret Knight and two other girls participate in the 1926 Miss Chicago contest.

#9 Miss Chicago contestant Lucille Burgess with Betty Blythe, 1926.

#10 Maebelle Soller at the Miss Chicago contest, 1926.

#11 Myrtle Christine Valsted, 17, became Miss Chicago 1927 after the original winner was found to be married; Valsted competed in the Atlantic City pageant of 1927 and then moved to Hollywood to pursue an acting career, but died one year later following surgery for appendicitis.

#12 Myrtle Christine Valsted, 17, was Miss Chicago in 1927.

#13 Virgina Stonesifer, Betty Ann Savers, Doris Rutkin, Margaret Dorney, Novene LaRue, and Myrtle Christine Valsted in the Miss Chicago contest, 1927.

#14 Mrs. Wallace Ford models a dress that she will wear to the Miss America costume for arts ball at the Stevens Hotel, 1927.

#15 Miss America Lois Delander, 16, won the Miss Illinois contest and went on to compete in Atlantic City for the Miss America title, 1927.

#16 Miss America Lois Delander with her parents, 1927.

#17 Estelle Kosloff, 20, won the Miss Chicago beauty pageant in 1927 but was disqualified when the pageant found out she was recently married; Myrtle Christine Valsted, 17, was runner up and therefore became Miss Chicago 1927.

#18 Ella Van Hueson, 22, was chosen as the most beautiful of 32 girls from various parts of the United States entered in the third annual International Pageant of Pulchritude in Galveston, Texas and was given the title of “Beauty Queen of the United States” before becoming Miss Universe, 1928.

#19 Miss Universe Ella Van Hueson, 22, arrived home in Chicago for a parade in her honor after winning the International Pageant of Pulchritude in Galveston, Texas, 1928.

#23 Beauty queen Evelyn Cushing, 24, won Miss Illinois in 1932 and went on to compete for Miss America.

#25 Candidates for the title of Miss Great Lakes on State Street, 1935.

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Written by Rachel Mitchell

Rachel Mitchell is a vintage fashion enthusiast with a passion for all things retro. She is interested vintage fashion styles, trends, and accessories, and provides tips and tricks for incorporating vintage pieces into modern wardrobes.

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