1920 Dress Up Ideas: 8 Looks From Flapper to Chaplin

Kate Threads

Two women standing in 1920s patterned beach pajamas and wide-brimmed hats.

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The ideas here run from a Charlie Chaplin costume built almost entirely from your own closet to a beaded cloche over a lace gown, and what picks one for you is the kind of party you are dressing for.

A daytime tea or garden party suits a drop-waist day dress in a soft color, a beach or pool party calls for pajamas or a vintage swimsuit, and an evening event wants the floor-length gown.

1. Flapper Dress

The black lace trim adds texture to this forgiving flapper dress style. · 📷 @_isabelchan_

A loose, straight cut with the waist dropped to the hips is what makes a flapper dress read as 1920s, and the fit is forgiving because nothing needs to cling.

A flapper dress with black lace trim adds texture without any extra beading, so you can keep the rest of the look simple.

Check the hemline before buying. Knee-length shows off knee-high socks and T-strap heels, which is the pairing I would pick for a daytime party.

Shape matters less here than length: a dress that hangs straight from the shoulders works on almost any body.

Gone were the constrictive corsets, excessive petticoats, and long bloomers. “The men won’t dance with you if you wear a corset,” a collective of flappers said to The New York Times in a 1920 report.

— Harper’s Bazaar

2. Gangster Girl Costume

A tailored pinstripe suit with a fedora gives this gangster costume its edge. · 📷 @laralazia

Borrowing the menswear half of the decade gives this costume its edge, and a suit with a fedora and tie is the whole foundation.

Feminine touches are the decision to make: I would soften a pinstripe suit with a pair of heels or a bold lip rather than pile on props.

Tailoring is the thing to check. A jacket that is too big looks like a costume, while one that fits the shoulders looks deliberate.

A group in matching suits makes the strongest photo, so coordinate with friends before you shop.

3. Beach Pajamas Outfit

Wide-legged pajama trousers create a comfortable and stylish beach outfit. · 📷 @historicpajama

Wide-legged pajama trousers, a matching loose jacket and a wide-brimmed sun hat make up this outfit, and it may be the most comfortable option on the whole list.

A bold pattern is what sells it, so I would choose a print over a solid.

Look in the sleepwear or resort section for wide-leg pants, then add a jacket cut in the same fabric if you can find one. Matching the 2 pieces matters more than the exact print.

It suits a daytime or outdoor party well, since nothing about it restricts movement.

4. Suffragette Costume

A 'Votes for Women' sash makes this costume easy to put together. · 📷 @profheatherjz

A sash reading "Votes for Women" is the one piece that tells people who you are, so start there. Pair it with a high-collar blouse and a plain black skirt, and the outfit is done.

Both the blouse and skirt are easy to find in your own closet, which makes this the cheapest idea here. Make the sash yourself from a wide strip of fabric with the lettering added in contrasting color.

I like it for events where you want a costume with a point of view, though it is quieter than a sequined look.

5. Floor-Length Gown

A beaded cloche cap enhances the elegance of a floor-length gown. · 📷 @classicvintagebydebbie

A floor-length gown suits the evening end of a 1920s party, and a beaded cloche-style cap over a lace dress does more for the era than extra jewelry would.

Lace in white or cream leans bridal, so decide up front whether you want that look.

Length is the main check: a hem that skims the floor needs shoes you can walk in. I would put money into the headpiece before anything else, because it signals the era faster than the dress does.

6. Charlie Chaplin Costume

A black suit and cane make for an easy Charlie Chaplin costume. · 📷 @shagunsingh_official

Charlie Chaplin is a gift for anyone who would rather skip sequins: a black suit, a black hat, a curved cane and a drawn-on mustache are the whole costume.

Most of it can come from your closet, so the cost stays low.

Use eyebrow pencil or eyeliner for the mustache and keep it small and neat. A three-piece suit with a vest gives the best silhouette.

It works best at a party where people will recognize the reference, so I would save it for a crowd that loves old films.

7. 1920s Vintage Swimsuit

A dark, belted one-piece swimsuit captures the essence of the 1920s. · 📷 @classicvintagebydebbie

A 1920s swimsuit is a dark, belted, tank-style one-piece, and that plain shape is what you are copying.

Black or another deep solid reads closest to the era, so a modern tank swimsuit in a dark color is a fair starting point.

The belt is the detail to settle first. A narrow belt at the hips gives the drop-waist line that separates this from an ordinary bathing suit, and a thrifted leather or fabric belt will do.

I would keep it to a beach, pool or lakeside party, since it is a swimsuit and nowhere else will feel right. Bring a few friends in matching dark suits for the strongest effect.

8. Drop-Waist Day Dress

Pastel colors and a fur stole add charm to this drop-waist day dress. · 📷 @iridessence

Peach gives this drop-waist dress a soft, daytime feel, and the accessories do the rest: a fur stole, a gold choker, a turban-style headband and T-strap shoes.

Thrift stores are the best place to hunt for the stole, and faux fur works as well as any.

Choose the headband before the jewelry. A turban-style band sits close to the head and ties the era together faster than a necklace can.

Pastels suit a tea or garden party better than a night out, so I would pick this for an afternoon. Keep the dress simple and let two or three accessories carry it.

Hair and Makeup Tips

Finger waves are the hairstyle I would build around, and bobs are the other classic choice. If your hair is long, pin it up under a headband so the shape reads as short from the front.

For skin, aim for pale and porcelain.

Line the eyes heavily and smoke them out, then finish with a ruby red lip. That combination looks glamorous without any extra effort on the outfit.

Keep one feature dominant, though. Smoky eyes and a bold lip together are the look, but a glittering hair accessory is the third thing the eye has to read, so I would choose one sparkly piece and skip the rest.

Practice the eye makeup a day early. Smoky liner is easy to overdo, and blending takes a few tries.

DIY Costume Ideas

Thrift stores are the best starting point for a budget look, and they make the costume harder for anyone else to copy.

Go in with a shape in mind, such as a straight, loose dress, rather than a specific color, and you will find more options.

Check the fabric before the size. Thin chiffon, lace or velvet in a loose cut can be taken in with a few safety pins, so a dress that is slightly off still works.

Plain pieces are worth buying because you can dress them up yourself. A long strand of pearls, a beaded belt or a feather headband turns an ordinary dress into a costume, and you can often find all three secondhand.

Set a limit before you shop. Two or three finds that work together beat a bag of pieces that never quite match.

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