How to make a costume for the Orphan Jessie in the play Annie

Jessie is one of the six orphans of the well-known Broadway musical character Annie which is looked up to by little girls around the globe.    Annie is a comic strip popularly known as “Little Orphan Annie” created by Harold Gray in 1924.  Jessie’s character is a ten year old girl, an orphan and is considered to be one of the major roles in the play -  Annie since she is one of the singers of the Never Fully Dressed which are sang by the girls in the orphanage.  If you are going to play Jessie’s character; here’s how to do a Jessie costume:

Things you need:

Simple Dress (preferably old or second hand) or Plain shirt, colored skirt, top

Hair pins / Hair bands colored

Black long wig or a Rapunzel Hair style wig

White long socks

Plain Black shoes

Cut clothes in small squares (in different colors)

 Steps in Making Jessie’s Costume:

Step 1: Try to look for simple dresses preferably the ones who look old.  You can use a simple white shirt and a knee-length colored skirt.  You can put a colored top on the shirt to make her costume noticeable even at the back of the audience. Keep in mind that it should look plain and simple since Jessie is living in an orphanage.

Step 2: You may also use a long white sock and an old black shoes; this was a common get-up during the time of Annie so you can make a perfect costume for a Jessie character.  You may also have other simple color combination of socks and shoes depending on your fashion sense.

Step 3: For the hair you can make it two pony tails both on the sides to make it look like a 10 year old girl or you can also use long black hair wig which is made Rapunzel hair style if preferred.  Bear in mind not to use a red wig since this is the trademark of Annie so  that when they see a red-haired character they could easily distinguished Annie from the group.

Putting Hair Bands will also enhance Jessie’s hair-do if you prefer her hair not to be in pony tail or Rapunzel’s style.  Do not use silk cloth since this signifies wealth better use a colored cloth as hair band.

Step 4: You can also put some accessories like a cut square clothes to make it appear like the dress or skirt is repaired and or worn out.

Step 5:  You may also watch the previous Annie musicals played in You tube  or the movie musical Annie starring Aileen Quinn and look for the character of Tessie and how she was dressed; this can give you an idea of Jessie’s dress

There is no commercially available Jessie costume since the orphan appearance varies from every production.   The appropriate clothes can be found at a thrift store or a second hand shop.  

Step 6: You may also consult the director of the show about what is his vision of the orphans so he can give you additional inputs on dressing Jessie.

Be creative and have fun in making Jessie’s costume.

Tips and warning:

1)      Since there is no commercially available Jessie’s costume because the orphans

appearances varies in every production, a simple and old girl’s dress is a perfect costume for a Jessie character; just keep in mind that it should look like simple, plain and a poor girl’s dress.  Anyone who sees it will know that the girl belongs to a very poor class hence unable to dress well.

2)      Do not be afraid to be creative.  You may use cut clothes to accentuate the skirt or you may also cut it so it would look like it is worn out.

3)      Dressing Jessie will not tame your freedom for fashion.  Even if it’s simple your creativity in color combination will be enhanced.

4)      You may customize and look for simple accessories; it will do justice to the character.