Broadway’s Top Do It Yourself Halloween Costumes: Annie

TheaterMania’s favorite DIY Broadway Halloween costumes, Part IV

Broadway is the best place outside of Comic-Con to grab inspiration for a Halloween get-up, but we’re aware that not everyone has access to Evita’s dress or costumer Susan Hilferty’s budget. So we tapped our own in-house make-up and costume guru Josh Hibbard to put together our Top D.I.Y. costumes inspired by shows currently running on Broadway.

Halloween is obviously not just for adults, even in New York City (“N-Y-Ceeeeee!”). That’s why we invited the adorable Kayla in to model our only child’s costume of the DIY series: Little Orphan Annie from the throwback comic and new Broadway revival of Annie, now playing at the Palace Theatre.

Annie is a spot-on choice for your pluckiest daughter/niece/granddaughter: She’s an orphan with an irrepressible spirit who cares a great deal about New Deal politics. Like a triple-threat Pollyanna, she’ll tap dance her way into your heart; and her contagious optimism will make you believe that the sun will come out tomorrow.

An additional plus when considering Annie’s iconic get-up is that it’s an insanely easy costume to assemble. Avoid costume shops entirely—pre-packaged Annie costumes can run upwards of $80. Instead, get a plain red dress (a child’s size is ideal, but if you’re on a tight budget you can roughly alter an adult dress instead), red wig (again, costume shop Annie-fro wigs are expensive, so look for a cheaper one and get creative with pins and clips), black Mary Janes, a few pieces of blank computer paper and you’ve got it. In our case, Josh sized down a cheap red witch’s dress into a child-appropriate Annie dress—something anyone can do with a pair of scissors and a prayer, saving mom Daddy Warbucks-style dough in the wardrobe department. Josh also repurposed an extra red wig with pins for the Annie ‘do and used scissors to cut white computer paper into a collar and belt to add to the dress with tape. What’s the verdict from our cutie-pie?

“I like the dress!” Kayla say, while playing with its hem.

The costume is also very light on makeup. Use Mehron red face paint to draw on freckles, blot over them with a makeup sponge and you’re ready to go!

(Bonus points if you have a big shaggy dog to play Sandy while you go trick-or-treating.)

A theater-loving 6-year-old looking for a less heroic approach (villains are more fun) might want to consider dirtying up the dress and wig, yanking off the collar, smudging some black eye shadow on her cheeks and going as little Madame Thenardier from Les Miserables (the film comes out this Christmas, so this will look fashion forward)…ah well, maybe next year.

Click here to see our DIY Chaplin Costume.

Items Needed (click on the links below to buy everything you need online):

Red Annie Dress

Hair ties or bobby pins

Red Annie Wig

-White Belt and Collar (can be made out of paper)

Flat black Mary Janes

Mehron red face paint


1. Put on the dress, sizing as necessary.

2. Pin the hair back.

3. Place the wig.

4. Pin up and style the wig to your liking.

5. Put on the belt (it can be real, or like ours made out of paper).

6. Use a small brush to draw on Annie’s freckles with Mehron red face paint.

7. Don’t forget the signature Annie collar (also be made of paper if not a part of the dress)…or being adorable.

Check back next week for the final installment of our DIY Broadway Halloween Costume Series.

Click here to see our DIY Hipster Elphaba costume.

Click here to see our DIY Cyrano costume.