1920s Shoes

Our 1920s shoes bring the spirit of the Jazz Age to your 1920s outfits, pairing perfectly with original vintage, retro, and inspired-by looks for both day and evening. The 1920s were a time of flappers, fun, and freedom, an age of women's liberation and independence. Ladies were cutting their hair and showing their legs for the first time, with exciting flapper shoes to show off and catch the eye. With metallic leathers and fabrics, fancy t-straps, rhinestones and lacquered heels, 1920s shoes were the epitome of flirty footwear for evening, while dapper oxfords, two-tone spectators, and mary janes made for smart daytime looks. Our selection of 1920s shoes have been chosen to reflect these iconic details on original vintage shoes and will take your flapper dresses, Gatsby frocks, and Downton Abbey outfits to the next level.

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Evelyn Retro Oxfords by Royal Vintage (Navy/Brown)

The 1920s and 1930s were a fabulous time for women's sportswear, and here we present the perfect dapper 1920s shoes to complete a sporting look. Meet Evelyn, inspired by men's spectator oxfords and fit perfectly for a lady of supreme fashion. The Evelyn oxfords are made in lightweight canvas paired ..

$150.00

Evelyn Retro Oxfords by Royal Vintage (Tan/Brown)

How better to complete a 1920s or 1930s sporty ensemble than with a perfect pair of Evelyn oxfords in the ever-popular tan and brown combo? These retro spectator oxfords are made of tan canvas combined with a rich brown leather on a 2 3/8" / 6 cm Spanish heel and insole arch support. Evelyn's dapper..

$150.00

Lillian Retro Spectator Shoes by Royal Vintage (Navy/Ivory)

There's little else as iconic as a spectator shoe, except perhaps the classic 1920s Mary Jane style. Why settle for a boring character shoe when the sporty, yet elegant, Lillian is calling your name? Made in real leather in the popular navy blue and ivory colorway, these 1920s shoes offer a real sid..

$150.00

Lillian Retro Spectator Shoes by Royal Vintage (Sage/Ivory)

1920s shoes were well-known for being flashy, flirty, and fashionable, with eye-catching details and interesting color combinations. Our Lillian holds these style ideals close at heart, with two-tone spectator styling in a classic 1920s colorway of popular sage green and soft ivory. The Lillians are..

$150.00

Roxy 1920s Flapper Shoes by Royal Vintage (Gold)

The name on everybody's lips is gonna be "Roxy." Style in spades is the goal of these glam mary jane shoes. Made in two-tone gilded leather and fastened with a center-closing rhinestone buckle, the Roxy are the metallic 1920s shoes you've been looking for, dreaming of, lusting after. With a 2 3/8" /..

$150.00

Roxy 1920s Flapper Shoes by Royal Vintage (Silver)

Beautiful, sparkly, shiny, gorgeous. The glamour of the Jazz Age comes alive in these stunning metallic silver Mary Janes, ready to hit the dance floor for a flapper fun night out or stop traffic in a '30s Old Hollywood evening gown. Named for Roxy Hart in "Chicago," our two-tone silver Roxies are m..

$150.00

Evelyn Retro Oxfords by Royal Vintage (Tan/Brown)(Imperfect) -$30.00

Evelyn Retro Oxfords by Royal Vintage (Tan/Brown)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Evelyns in brown/tan for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfe..

$150.00 $120.00

Galaxy Two-Tone T-strap Shoes by Chelsea Crew (Burgundy/Beige) -$28.00

Galaxy Two-Tone T-strap Shoes by Chelsea Crew (Burgundy/Beige)

Step into the past with these fancy flapper shoes! The Galaxy Two-Tone T-Straps in rich burgundy and beige are just the style to lend a little Jazz Age flair to your wardrobe. Whether you dress with a dash of retro style or are looking for beautiful shoes to wear with your modern outfits, the Galaxy..

$68.00 $40.00

Gamma Mary Janes by Chelsea Crew (Black) -$25.00

Gamma Mary Janes by Chelsea Crew (Black)

Gamma Mary Janes are a great choice for any retro inspired wardrobe. Perfect for 1920s and 1930s but with more interesting details than a character shoe, the Gamma Mary Janes are a lovely little heel with a gracefully pointed toe, sweetheart vamp, thin strap with adjustable buckle, and a comfortable..

$65.00 $40.00

Gamma Mary Janes by Chelsea Crew (Burgundy) -$25.00

Gamma Mary Janes by Chelsea Crew (Burgundy)

Gamma Mary Janes are an excellent all-around shoe for all season. Perfect for 1920s but with more interesting details than a character shoe, the Gamma Mary Janes are a pretty little heel with a gently pointed toe, sweetheart vamp, thin strap with buckle, and comfortable heel height. Sticky rubber so..

$65.00 $40.00

Gamma Mary Janes by Chelsea Crew (Navy) -$25.00

Gamma Mary Janes by Chelsea Crew (Navy)

Gamma Mary Janes are the wardrobe staple you've been looking for. Perfect for 1920s but with more interesting details than a character shoe, the Gamma Mary Janes are a pretty little heel with a gently pointed toe, sweetheart vamp, thin strap with buckle, and comfortable heel height. Sticky rubber so..

$65.00 $40.00

Gamma Mary Janes by Chelsea Crew (Navy)(Imperfect) -$35.00

Gamma Mary Janes by Chelsea Crew (Navy)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Gamma in Navy for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfect shoe..

$65.00 $30.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Black/White) -$23.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Black/White)

Dance a mile or two at your 1920s flapper-themed party in our iconic Gatsby two-tone t-strap vintage shoes. These cute and iconic 1920s shoes are perfect for dancing or just looking snazzy with any outfit, vintage or modern. Gatsby features patent leather brogue detail on matte leather, adjustable b..

$68.00 $45.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Black/White)(Imperfect) -$33.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Black/White)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Gatsby in black/white for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperf..

$68.00 $35.00

Gatsby Two-Tone T-Strap 1920s Shoes by Chelsea Crew (Bronze/Gold) -$23.00

Gatsby Two-Tone T-Strap 1920s Shoes by Chelsea Crew (Bronze/Gold)

Flashy footwear was a great love of the Jazz Age, paired with sparkling gowns and fringed frocks. Capture the spirit of the 1920s with our Gatsby two-tone t-strap vintage shoes in shimmering metallic gold with bronze brogue detail, adjustable buckle closure, and 3" high Spanish heel. These retr..

$68.00 $45.00

Gatsby Two-Tone T-Strap 1920s Shoes by Chelsea Crew (Bronze/Gold)(Imperfect) -$33.00

Gatsby Two-Tone T-Strap 1920s Shoes by Chelsea Crew (Bronze/Gold)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Gatsby in bronze/gold for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperf..

$68.00 $35.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Navy Blue/White)(Imperfect) -$33.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Navy Blue/White)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Gatsby in navy/white for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfe..

$68.00 $35.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Red/White) -$23.00

Gatsby Two-Tone T-strap 1920s Shoes by Chelsea Crew (Red/White)

All dapper flappers need a great pair of flashy 1920s style shoes to complete their retro look. The '20s was a wonderful decade for beautifully designed, eye-catching footwear, as hemlines rose and women were freer than ever to express themselves. The Gatsby two-tone t-straps embody this fabulously ..

$68.00 $45.00

Lillian Retro Spectator Shoes by Royal Vintage (Navy/Ivory)(Imperfect) -$30.00

Lillian Retro Spectator Shoes by Royal Vintage (Navy/Ivory)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Lillians in navy/ivory for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imper..

$150.00 $120.00

Lillian Retro Spectator Shoes by Royal Vintage (Sage/Ivory)(Imperfect) -$30.00

Lillian Retro Spectator Shoes by Royal Vintage (Sage/Ivory)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Lillians in sage/ivory for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imper..

$150.00 $120.00

Londoner 1920s Oxfords by American Duchess (Cherry)

The Londoner Oxfords by American Duchess are the quintessential choice for early 1920s and Edwardian attire. With tone-on-tone broguing drawing inspiration from vintage menswear, these gorgeous ladies' lace-ups feature a pointed toe, stacked heel, and a patina finish for an authentic look and feel. ..

$160.00

Londoner 1920s Oxfords by American Duchess (Tan)

The Londoner Oxfords by American Duchess are the quintessential choice for early 1920s and Edwardian attire. With tone-on-tone broguing drawing inspiration from vintage menswear, these gorgeous ladies' lace-ups feature a pointed toe, stacked heel, and a patina finish for an authentic look and feel. ..

$160.00

Mandy Retro Mary Jane Shoes by Chelsea Crew (Black/White) -$22.00

Mandy Retro Mary Jane Shoes by Chelsea Crew (Black/White)

Mandy Retro Mary Janes give you the best bang for your footwear buck with amazing retro styling in eyecatching black and white spectator design. With a wide, adjustable strap, fancy brogue cutouts, and a sturdy welted sole, the Mandy Retro Mary Jane are an excellent all-season shoe for retro, vintag..

$67.00 $45.00

Mandy Retro Mary Jane Shoes by Chelsea Crew (Tan) -$22.00

Mandy Retro Mary Jane Shoes by Chelsea Crew (Tan)

Mandy Retro Mary Janes are full of lovely retro styling in a beautiful brogued spectator design. With a wide, adjustable strap, fancy detailing on the toe and heel, and a sturdy welted sole, the Mandy Retro Mary Jane are an excellent all-season shoe for retro, vintage, and modern outfits...

$67.00 $45.00

Matis Oxfords by Chelsea Crew (Tan)(Imperfect) -$33.00

Matis Oxfords by Chelsea Crew (Tan)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Matis in tan for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfect shoes..

$65.00 $32.00

Moscato Two-Tone Oxfords by Chelsea Crew (Black/Ivory) -$23.00

Moscato Two-Tone Oxfords by Chelsea Crew (Black/Ivory)

An eye-catching pair of two-tone oxfords is a surefire way to add retro styling to outfits both vintage and modern. Interesting from all angles, the Moscato two-tone oxford shoes feature broguing throughout, curvaceous detailing, and a sophisticated black and ivory color scheme. The sturdy, low heel..

$68.00 $45.00

NOS 1920s Mary Janes by St Louis Queen (Nude) -$50.00

NOS 1920s Mary Janes by St Louis Queen (Nude)

An original pair of 1920s mary jane shoes is a true vintage treasure. These nude and peach round-toed shoe feature a narrow strap and button closure, leather soles, and a painted wooden heel. *Please Note - the paint on these heels is chipped in some place. The price reflects this.MeasurementsInsole..

$120.00 $70.00

NOS Vintage Leather T-Strap Sandals (Red) -$50.00

NOS Vintage Leather T-Strap Sandals (Red)

A fun pair of low-heeled original vintage sandals in bright red. These mary janes are cute and casual and will work for both casual ladies and children.MeasurementsInsole - 8.9" / 22.5 cmWidth - 3" / 7.7 cmHeel Height - 0.7" / 1.8 cmAbout New Old Stock (NOS)New Old Stock shoes have never b..

$120.00 $70.00

Panther Retro Flats by Chelsea Crew (Black) -$20.00

Panther Retro Flats by Chelsea Crew (Black)

Panther Retro Flats are the perfect way to add a bit of retro flair to your outfit while staying cute and comfortable all day long. Made of lovely black microsuede with a rubber sole, the fringe detail on the vamp and tapered toe of the Panther Retro Flats lends that vintage feel to these versatile ..

$55.00 $35.00

Panther Retro Flats by Chelsea Crew (Red) -$20.00

Panther Retro Flats by Chelsea Crew (Red)

Panther Retro Flats are an adorable way to add a bit of retro flair to your outfit while staying cute and comfortable all day long. Made of quality microsuede with a rubber sole, the tapered toe and fringe detail on the vamp of the Panther Retro Flats gives interest and that vintage feel to these ve..

$55.00 $35.00

Petroleum Art Deco Booties by Aerosoles (Black) -$40.00

Petroleum Art Deco Booties by Aerosoles (Black)

Vintage catalogs are full of beautiful shoes with interesting details. These Art Deco elements are brought back to life in the interesting lattice design on the vamp of the Petroleum Art Deco Booties by Aerosoles. The arresting vamp, round toes, and beautiful grey microsuede combine to make the Petr..

$80.00 $40.00

Petroleum Art Deco Booties by Aerosoles (Grey) -$40.00

Petroleum Art Deco Booties by Aerosoles (Grey)

Vintage catalogs are full of beautiful shoes with interesting details. These Art Deco elements are brought back to life in the interesting "cage" design on the vamp of the Petroleum Art Deco Booties by Aerosoles. The arresting vamp, round toes, and beautiful grey microsuede combine to make the Petro..

$80.00 $40.00

Roxy 1920s Flapper Shoes by Royal Vintage (Silver)(Imperfect) -$30.00

Roxy 1920s Flapper Shoes by Royal Vintage (Silver)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Roxies in silver for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfect s..

$150.00 $120.00

Sally Saddle Shoes by Chelsea Crew (Black/White) -$20.00

Sally Saddle Shoes by Chelsea Crew (Black/White)

A true classic, the Sally saddle shoes are great for any decade, particularly 1940s. Pair them with bobby sox, and wear with trousers, skirts, or dresses. The Sallies are lined in leather and feature red-brown crepe rubber soles, perfect for the sock hop or soda fountain. A true American classic, Sa..

$60.00 $40.00

Sally Saddle Shoes by Chelsea Crew (Black/White)(Imperfect) -$30.00

Sally Saddle Shoes by Chelsea Crew (Black/White)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Sally Saddle Shoes for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfect..

$60.00 $30.00

Sergi Vintage T-straps by Chelsea Crew (Gold)(Imperfect) -$33.00

Sergi Vintage T-straps by Chelsea Crew (Gold)(Imperfect)

If a few small cosmetic flaws don't bother you, snag yourself a pair of Sergis in gold for a great deal. Imperfect shoes exhibit minor flaws and don't quite meet our strict quality standards. Flaws include rubs, bumps, scuffs, cuts, pebbling, discoloration, or dirty spots on the shoes. Imperfect sho..

$68.00 $35.00

Shoreline 1920s Mary Janes by Aerosoles (Black) -$20.00

Shoreline 1920s Mary Janes by Aerosoles (Black)

A good 1920s style shoe can be hard to find, but we've got the perfect fit for you. The Shoreline 1920s Mary Janes are an excellent choice for a little flapper fun, day or evening. A good all-around shoe in black with a buckle strap, low heel height, comfortable and hard-wearing sole, and lovely ret..

$60.00 $40.00