"Annie" Costume Ideas



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“Annie” Costume Ideas

Below are some ideas for costumes for our “Annie” cast and chorus. This show takes place in the 1930’s. It might be fun to be as authentic to the time period as possible. You tube videos of other schools performing the show are a good place to look for costume ideas. Thrift shops are a great place to look for clothing and accessories.

When creating your costume, keep in mind that the cafeteria is often very warm in May – especially under the stage lights. Let me know if you have any questions.

Can you help? Some props we still need are:

A blue Tiffany’s box

Old school square suitcases (no wheels) – we need 4



Orphans – All chorus members: The chorus should appear ragged and shabby. Layering ill-fitting, unkempt, mismatched and faded clothing is the trick to create this look. Possible thoughts for boys and/or girls can be clothes with patches, pants with holes, old plain t-shirts, slightly ripped shirts, smocks, a jumper with a contrasting shirt and holey socks. Hand-me-downs are good ideas. Drab or faded colors are best. Hair can have a slightly uncared-for look.

Miss Hannigan: Hannigan should wear a dress that is tawdry and looks well-worn. A faded print is perfect. Tacky touches such as unkempt hair, rolled down socks and many long beads or a boa will work well. She also needs a whistle around her neck. Lastly, a big sweater or drab coat is worn for her trip to the Warbucks Mansion.

Annie: Annie should be dressed like the other orphans: layers of ragged clothing, a patchy jumper, tattered socks? She’ll need an oversized thin sweater for her escape from the orphanage. Annie’s trademark is her hair. An unkempt reddish wig, or hair styled in a similar fashion is ideal.

For NYC, Annie should wear a coat (maybe with a faux fur collar) over her orphan costume. A heavy coat might be too hot under the lights. The big reveal is in Scene 5 when Annie appears like the comic strip, wearing her trademark short-sleeved red dress with white collar, white ankle socks and black strap shoes. Her hair (or wig) should be tight and curled.



Bundles/Tourist/Louis Howe: Bundles could wear a short sleeve dress shirt and work pants. Maybe you can find a casual deliveryman’s cap. Adding a jacket can turn Bundles into a tourist walking outside. Louis Howe is Roosevelt’s aide and should be professionally dressed. The outside jacket comes off and is replaced by a suit coat or dark jacket and tie.

Apple Seller/Tourist/Usher: The cold weather street vendor should wear an oversized sweater, scarf and hat. Knit gloves with the fingers off add an authentic touch. To hold the apples, a tray with a neck strap would be terrific. The gloves come off for the NYC tourist and the sweater changed to a jacket. The switch to usher is quick – probably just enough time to take off the jacket.

Lt Ward: A classic police uniform (navy blue shirt and pants) is perfect for this character. You could also attach a set of keys or fake handcuffs to a belt, add a badge and wear boots to add authenticity. Perhaps a policeman’s hat?

Sandy: You can do a one-piece costume or sleeper pajamas or just go with tan or beige shirt, pants and matching socks. Ears can be made by adding material to a baseball hat or put hair in pigtails!

Grace Farrell: Grace dresses as a stylish professional in a 30’s style suit or dress, hat and gloves. She will need to add a coat in NYC. If you want, you could change your look for Scene 5 but it is not necessary.

Drake and the Servants/Tourists: All the servants are neatly groomed and take a great deal of personal pride in their appearance. Male servants should wear white shirts and black pants. For female servants, a simple black dress (or black top and black skirt) with a white apron and maid’s cap would be perfect. A feather duster is a good prop. Footwear should be black sneakers/shoes for boys and girls. Drake should look polished and formal. White gloves, white shirt, black pants, black vest and ascot or a cummerbund and Drake is ready to serve. When the servants become tourists, aprons are off and a jacket or sweater covers the servant costume.

Oliver Warbucks: Clothes make the man with this debonair gent. Oliver Warbucks is always dressed formally in a dark suit, white shirt and bow tie. Warbucks needs an overcoat and maybe a fedora for NYC.

Rooster Hannigan: Rooster’s costume should be as colorful as his personality. A colorful shirt, suspenders, a fedora, and pants turned up to make 1930’s cuffs would also be fabulous. He’ll need an overcoat when “in disguise” in Scene 7. A fake nose-moustache-glasses disguise would also be great for this scene!

Lily St. Regis: The sky is the limit for Lily’s gaudy and tasteless attire! She should be as outlandish as Rooster is gaudy. A brightly colored dress, complete with handbag and pumps will complete her persona. Lily also needs a coat and large hat or shawl for her disguise in Scene 7.

Bert Healy/Tourist: This character should look as smooth as he sounds on the air. He can have a touch of flamboyance with a striped jacket, bow tie and skimmer hat. A coat can cover this costume for NYC.

President Franklin D. Roosevelt/Tourist: Our 32nd president will sit in a wheelchair (Mrs. Lenton will provide) and is impeccably groomed with a dark suit, white shirt, tie and small spectacles. For NYC, the suit coat is replaced with an overcoat.


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