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) (Pre-Order) -$20.00

Evelyn Retro Oxfords by Royal Vintage (Navy/Brown) (Pre-Order)

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 $130.00

Evelyn Retro Oxfords by Royal Vintage (Tan/Brown) (Pre-Order) -$20.00

Evelyn Retro Oxfords by Royal Vintage (Tan/Brown) (Pre-Order)

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 $130.00

Lillian Retro Spectator Shoes by Royal Vintage (Navy/Ivory) (Pre-Order) -$20.00

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

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 $130.00

Lillian Retro Spectator Shoes by Royal Vintage (Sage/Ivory) (Pre-Order) -$20.00

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

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 $130.00

Roxy 1920s Flapper Shoes by Royal Vintage (Gold) (Pre-Order) -$20.00

Roxy 1920s Flapper Shoes by Royal Vintage (Gold) (Pre-Order)

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 $130.00

Roxy 1920s Flapper Shoes by Royal Vintage (Silver) (Pre-Order) -$20.00

Roxy 1920s Flapper Shoes by Royal Vintage (Silver) (Pre-Order)

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 $130.00

Astoria 1920s Shoes by American Duchess (Black)

A true early 20th century reproduction, Astoria 1920s Shoes by American Duchess offer glamour and interest for 1920s day and evening attire. Designed by independent historic footwear designer American Duches, the Astoria vintage shoes are the perfect addition to an old-fashioned wardrobe. Astoria fe..

$160.00

Astoria 1920s Shoes by American Duchess (Ivory)

Beautiful and iconic, Astoria 1920s Shoes in ivory are the perfect early 1920s reproduction shoes for Jazz Age events both day and night. Astoria features all-leather construction, lattice straps closing with period-accurate buttons, and a 1.75" French heel. These beautiful vintage shoes offer comfo..

$160.00

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

Galaxy Two-Tone T-strap Shoes by Chelsea Crew (Navy/Cream)

Do you love fancy footwear as much as we do? The Galaxy Two-Tone T-Straps in navy and cream are just the style to lend a little pizzaz to your wardrobe. Whether you dress with a dash of flapper fashion or are looking for interesting shoes to wear with your modern outfits, the Galaxy T-Straps are for..

$68.00

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

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

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

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

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

A snazzy flapper needs a great pair of classic 1920s style shoes to complete their retro look. The 1920s was *the* decade for beautiful footwear, as hemlines rose and women were freer than ever to express themselves. The Gatsby two-tone t-straps embody this fabulously flirty decade, especially in Su..

$68.00

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

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

Gibson Teardrop 1920s Shoes by American Duchess (Black)

A true vintage reproduction designed by historic shoemaker American Duchess, the Gibsons are fantastic early 1920s shoes, featuring a pointed toe, teardrop cutouts, lace closure, and a sturdy 2" Louis heel...

$145.00

Gibson Teardrop 1920s Shoes by American Duchess (Ivory)

Gibson by American Duchess is a faithful vintage reproduction, great for early 1920s daywear. These beautiful all-leather vintage shoes are fabulous for original vintage outfits as well as reproduction vintage, or just to add a little retro style to your modern attire. Gibson 1920s Shoes feature all..

$145.00

Gibson Teardrop 1920s Shoes by American Duchess (Tan)

Gibson 1920s Shoes by American Duchess are a true vintage reproduction, perfect for early 1920s events. These gorgeous vintage shoes are perfect for any vintage 1910s or 1920s outfit as well as to add a bit of retro style to your modern wardrobe. Gibson vintage shoes feature all leather materials, a..

$145.00

Lester Retro TStraps by Chelsea Crew (Red/White)

For a fun retro vibe, try the festive Lester Retro Tstraps in very vintage red and white. With a peep toe, adjustable buckle closure, and comfortable heel height, the Lesters are a great addition to your throwback wardrobe. These adorable shoes will go great with 1920s, 1930s, or 1940s outfits in su..

$65.00

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

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

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

Panther Retro Flats by Chelsea Crew (Black) -$10.00

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 $45.00

Panther Retro Flats by Chelsea Crew (Red) -$10.00

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 $45.00

Petroleum Art Deco Booties by Aerosoles (Black) -$10.00

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 $70.00

Petroleum Art Deco Booties by Aerosoles (Grey) -$10.00

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 $70.00

Sergi Vintage T-straps by Chelsea Crew (Gold)

The flirty fun of the 1920s and the sultry glamour of the 1930s is perfectly exhibited in the gorgeous Sergi Vintage T-Strap Shoes in a soft metallic gold. With stunning strapwork on the toes and the easy fit and adjustability of  the t-strap with buckle closure, the Sergi vintage shoes will ca..

$68.00

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

Tango 1920s Lace Up Boots by American Duchess (Black)

Fabulous and flashy, the Tango boots reflect the worldwide dance crazy in the late Edwardian and early 1920s. Popular for both day and evening, the gorgeous American Duchess Tango boots are made of all leather with leather soles, satin ribbons, and a reproduction 3" French heel. Tango are perfect fo..

$195.00

Tango 1920s Lace Up Boots by American Duchess (Oxblood)

Flawlessly flirty, the Tango boots celebrate the international dance craze in the late Edwardian and early 1920s. Popular for both day and evening, the gorgeous American Duchess Tango boots are made of all leather with leather soles, satin ribbons, and a reproduction 3" French heel. Tango are perfec..

$195.00