
Mid 20s tennis with middy tops, pleated skirts and tie necks
Preparing for the 2020 Great Gatsby event with a 1920s tennis outfit theme begins now! I have always wanted to do this theme and Oscar picked up some tennis sweaters and vests earlier this year, so we are almost all set. Our friends are joining us for a group costume-along, which always makes it more fun.
After doing some research, here is what I know about 1920s tennis outfits:
Women’s 1920s tennis outfits:
Most women wore 1920s white tennis dresses to play professionally. Casual players would wear whatever sporty day dress they had on hand. Cardigan sweaters often topped dresses, not during play (unless it was chilly) but before and after, for relaxing in-between games. These two pieces plus white shoes, stockings, a matching headband, and vintage wood tennis racket would complete a 1920s tennis dress outfit.
- White slip over a dress. Some are button-down, some have tie necks or small collars/Peter Pan collars with short or sleeveless tops and a drop waist skirt. The skirt is either straight but loose or pleated. A belt or sash band is optional. Colored dresses with these designs are also an option.
- A white pleated skirt with a middy top and blue or black necktie is very sporty for the ’20s
- Long cardigan sweaters with shawl collar or button-down. Many are sleeveless or cap sleeve cardigan vests. They were not always white but a light color is more summery. Some had monograms to the left lower side. The men’s style tipped V neck sweater wasn’t usually worn by women but still makes a 20s inspired outfit for matching couples.
- Headwrap / hair scarf or bucket hats were tennis hats of the day until the visor appeared in the late 1920s.
- White stockings (should not be sheer, I would choose white cotton tights). The late ’20s saw nude legs (Gasp!) with white fold down socks.
- White canvas or leather low heel Oxfords or the new rubber sole flat Mary Jane or Keds type sneaker. Two tone and saddle Oxfords are also an option.
- Vintage Tennis racket – wood frame rackets are not too expensive on eBay. I found a smaller Badminton racket at a thrift store from the 1970s that looks similar to ’20s versions.
Men’s 1920s Tennis outfits:
- White cloth pants – (cotton, duck cloth, linen, light wool blends) high waisted, turn up cuff
- Thin belt – brown or black leather
- White dress shirt – Unbuttoned with rolled-up sleeves
- A tennis sweater – White V neckline and contrast trim (usually blue, grey)
- White shoes – Canvas Oxfords, leather white or two-tone Oxfords, canvas high top Converse type sneakers in white or white with brown or black leather trim. White socks.
- Vintage Tennis racket – wood frame rackets are not too expensive on eBay
Here are some photos of 1920s tennis clothes:
- 1920 or earlier. Love the top with the boatneck collar.
- Blouse with Middy tie and purple skirt. Colorized.
- 1925 simple white slip over cotton tennis dresses with belt. Sleeveless on the right.
- 1926 tennis champs wearing pleated white tennis dress with button down cardigans and headwraps.
- Right cardigan is monogramed. Her dress also has the middy collar.
- Cardigan vest over tennis dresses.
- A vest over blouse, long skirt and two tone shoes
- 1922 a lovely knit plaid sweater with tie belt. Her floppy hat was also common in the early 20s.
- 1922 shawl collar cardigan with tie belt over white tennis dress
- 1922 day dress, pink floppy hat.
- 1922 girls Middy dresses with the inspiration for women’s tennis outfits
- 1921 this middy top day dress would be adorable for a casual tennis game
- Tennis sweater (men’s style) with pleated skirt
- A clean shot of a middy top with rolled sleeves! Skirt looks straight instead of pleated.
- Beautiful! Tie neck tennis dress with sleeveless cardigan
- A tied headband
- 1929 notice the visor hats and pearl necklaces! Love her spit curls too.
- 1929 the late 20s saw more Art Deco designs applied to tennis dresses
- Tennis team and coach
- Miss Fisher has a game of Tennis with her partner. Looks too modern but still very pretty.
- 1921 this man’s outfit is simple. White dress shirt with rolled sleeves. High waist white trousers, thin belt and white oxford shoes
- 1920s tennis sweater/ Cricket sweater
- Traditional men’s tennis sweaters with V striped trim. White duck cloth pants and oxford shoes complete the look.
- Bill Tilden’s tennis sweaters with contrast striped collar and cuffs
- Bill again, traditional sweater in center and white rolled sleeve shirt shirt unbuttoned collar.
- Pullover logo / monogram sweaters. Right mans shoes are Converse type sneakers.
- 1922, black and white sporty canvas shoes
- 1927 canvas bow mary jane rubber sole sport shoes for Tennis.
- 1920’s Women’s Sport Shoes in White Canvas
- 1924 mens sport shoes. White canvas with leather trim for a tone tone look or all white cap toe Keds type sport shoes, Right is white Converse type sneakers
- 1925 Keds sport shoes for men. Timeless!
- 1922 two tone sport sneakers
- 1927 sport shoes
1920s Tennis Dresses
Shopping for a 1920s tennis dress / outfit may seem tricky at first. In the sea of ’20s flapper dresses, you won’t find many options for day dresses, let alone a white tennis dress. However, you can fake-it-till-you-make-it with some other options.
1. A classic nurse dress/maid uniform. These white button-down dresses are a reasonable approximation to white ’20s shirtwaist dresses — and affordable, too. Add a belt or sash and necktie to give it a bit more ’20s styling.

Classic white nurses dress on Amazon
2. A white necktie/ bow neck dress is pretty popular right now, especially come spring/summer. Most will not have a drop waist, but everything else looks ’20s. Sleeveless shirt dresses /shirtwaist dresses are another easy to find option. Be sure to wear a white slip and underwear if the dress fabric is on the thin side.

A white tie neck dress is almost 20s.
3. La Vie Delight has some ’20s tennis dresses/sailor dresses in her line or she can modify another dress to look tennis ready. La Vie Delight can also make plus sizes on request.
4. eShakti dresses are perfect for customizing a dress into a 1920s style within budget ($100 or less). I could play all day with all the options they offer. For example, look at the white cotton dresses, especially the shirt dresses, drop waist, and tie neck designs. You can then choose a different neckline (I like Peter Pan), sleeve type (sleeveless), and skirt hem length (below the knee). You can also make the natural waist into a drop waist buy choosing a custom “High Point to Shoulder to Waist,” which for me is about 23 inches (you may need to adjust your waist measurement too). You can also choose an eShakti non-white dress and go to the “Fabric Customization” link at the top of the page to select a white fabric instead. Plus sizes up to 6XL available.
This is the option I think I want to try. I have done custom dresses with eShakti before and it is a blast to see how to designs online turn out in person (arriving in about 10 days too!)

I customized this eShakti dress by removing the sleeves, shortening the hem and adding a peter pan collar. Not shown is the drop waist I would create.

Two 1920s tennis outfit combinations

1920s Sporty Outfit, casual daywear

Men’s tennis outfit
Shop 1920s Style Tennis Outfits
Debbie Sessions has been teaching fashion history and helping people dress for vintage themed events since 2009. She has turned a hobby into VintageDancer.com with hundreds of well researched articles and hand picked links to vintage inspired clothing online. She aims to make dressing accurately (or not) an affordable option for all. Oh, and she dances too.