Applying the Bald Cap
Tie your hair back into a tight, low ponytail. If you have short hair, use a wide, elastic headband to keep it back. The key here is to create a smooth hairline. If you want to, you can apply some petroleum jelly to your hairline as well to protect it from the adhesive later. If you wish to use your own hair, make sure that it’s about shoulder-length first, then skip down to styling it. Apply the petroleum jelly to your hair rather than to your skin. Spirit gum is easy to remove them skin, but difficult to remove from hair.
Place a strip of cotton batting across your front hairline to add bulk. Pennywise has a large head, so if you want a more accurate look, you need to add some bulk. Tear off a strip of cotton quilt batting, then drape it across your front hairline and temples. Alternatively, stuff your bald cap with cotton batting instead. Don’t worry about gluing the batting down; the bald cap will help hold it in place.
Pull on a bald cap, making sure to tuck the cotton batting under it. Use your fingers to tuck any bits of cotton batting under the bald cap. Be sure to tuck your hair under the bald cap too, although you can leave your ponytail out, if you want to. A bald cap is not the same thing as a swim cap or a wig cap. You need to buy it online or in a costume shop. The color doesn't matter. If there’s too much bulk in the seams, pull the cotton batting downward with your fingers. Be careful so that it doesn’t peek out from under the cap, however. If you choose to leave your ponytail out, you'll need to tuck it under the rest of your costume.
Secure the side flaps of the bald cap with spirit gum. Peel up the loose side flaps of the bald cap. Apply some spirit gum, wait 10 to 15 seconds for it to get tacky, then press the flaps back down. Work 1 side flap at a time. Double-check your front hairline and glue down any other edges that appear loose. Spirit gum is a theatrical-grade adhesive used for prosthetics. You can find it online and in costume shops. Spirit gum contains a little brush inside the cap, like nail polish. Hold the cap and use the brush to apply the liquid.
Apply liquid latex to the edges of the bald cap with a makeup sponge. Open up a jar of liquid latex, then dip a makeup sponge into it. Pat the makeup sponge along the edges of the bald cap to blend it into your skin. Make sure that you get the front and temples, all the way down to your ears. Wait 1 to 2 minutes for the liquid latex to dry, then apply another coat, if needed. If the liquid latex is taking too long to dry, speed the process up with a hairdryer.
Pull apart some tissues, then tear them into smaller pieces. Peel apart a tissue into separate sheets. Tear the sheets into 1 to 2 in (2.5 to 5.1 cm) pieces. You will use these tissues to mimic the texture of caked-on face paint. Do this with 2 or 3 tissues so that they’re ready for you in case you run out. Your hands may get messy, so it’ll be easier to have all your tissues ready. If you don't have tissues, use toilet paper instead. Paper towels are not recommended because they are too stiff. Skip this step and the next for the Tim Curry version of Pennywise.
Apply the tissue pieces to the front of the bald cap with liquid latex. Use a makeup sponge to pat some liquid latex to a patch on the bald cap, then press a tissue piece into it. Cover the tissue up with more liquid latex. Repeat this process all over the front of your bald cap, from temple-to-temple. Start at the bottom edge of the bald cap and work your way up to the top-center of your forehead.
Adding and Styling the Wig
Pull on a cheap, orange wig, making sure to expose the high forehead. The exact length of the wig doesn't matter since you'll be cutting it, but something that goes a little past your shoulders would be great. Pull the wig back slightly so that the front sits close to the top-center of your head. For best results, choose a wig with straight fibers, although a wig with wavy fibers may also work. Don't use a curly wig. If you're worried about the wig slipping back, apply some spirit gum to the underside of the wig's hairline, then press it against the bald cap. If you are doing the Tim Curry version, use a straight, red wig instead. If you wish to use your own hair, comb it back, then spray your front hairline with white hairspray.
Cut the wig so that it’s about shoulder-length. Grab a random chunk of hair and chop it off with a pair of scissors so that it’s about shoulder-length. Grab another chunk of hair, and cut it as well. Do this for both sides of your head, then the back. Don’t worry too much about making it look neat. Pennywise doesn't have nice hair. Save the cut-off chunks of hair so that you can later attach them to the front of the wig to create the widow’s peak for the 2017 version of Pennywise. Skip this step if you’re using your own hair.
Tease the wig so that the strands stick out from your head. Again, don’t worry about being too neat here. Just grab chunks of hair in your fist and tease or backcomb them with a brush or comb. Do one side of your head first, then the other. Be sure to get the back as well. If you’re using your own hair, be sure not to tease too close to the front of your hairline. You want that hair to still lie smoothly against your scalp. To tease hair: pull the hair away from your head and comb it back towards the scalp. Use short, quick strokes.
Curve the hair on the sides of your head upward and set them with hairspray. Grab the hair on the left side of your head and pull the ends upward so that they curve a little. Set them with hairspray, then repeat the process for the right. The hair on the top of your head should go straight back. For the original 1990 version, make the hair stick straight out from your head on all sides, then mist it with hairspray. If you are using your own hair, you can use orange or red colored hairspray instead.
Use spirit gum and extra chunks of wig hair to create the widow’s peak. Apply spirit gum in an upside down triangle (like a widow’s peak) to your forehead, right in front of your wig. Grab a chunk of the cut-off wig hair and apply it to the spirit gum. For a fuller look, apply the hair to the spirit gum in rows, starting from the wider end of the triangle and finishing at the point. Skip this step if you’re using your own hair or doing the original Tim Curry Pennywise. If you’re using your own hair and want a widow’s peak, spray a triangle onto your forehead with orange hairspray.
Set the style with more hairspray. If you want to add more dimension to your wig, use colored hairspray instead, which you can find at a party, costume, or Halloween shop. The Tim Curry version of Pennywise has straight-up red hair, but the 2017 reboot version has hints of red, brown, and orange in it. If you do decide to use colored hairspray, retouch your hairline with white makeup.
Doing the Base Face Paint
Cover up your eyebrows with a glue stick. Use a spoolie brush to comb out your eyebrows, then rub a glue stick over them. Don’t rub the glue stick back-and-forth; instead, start at the inside corner of your eyebrow and finish at the end. For a smoother look, wait until the glue dries, then apply spirit gum over it. Only do this if you have spirit gum remover handy. A spoolie is essentially a mascara brush, but it comes with a longer handle, like a makeup brush. You can use an old, clean toothbrush instead.
Pat on white foundation to your neck, face, and ears. You can use an oil-based or water-based foundation, depending on your preferences. Apply the product to your skin using a makeup sponge and a patting motion. Be sure to get your entire neck, jaw, forehead, face, and ears. If you are using water-based makeup, you’ll have to dampen the sponge first. You can use a spray-on foundation on your forehead and neck, but you shouldn’t use it on your face because it's not precise enough. When doing your forehead, be sure to cover the bald cap too, all the way up to the wig.
Set the foundation with powder or setting spray. Use a powder brush to apply a light dusting of setting powder all over your face, forehead, and neck. This includes the bald cap! Alternatively, apply a light misting of makeup setting spray instead. This is mostly to set your "canvas." You'll be setting your makeup again at the end. “Baking” is a popular technique for applying setting powder, but you don’t need to do that for this stage. Save that technique for the end.
Brush on black eyeshadow to your eyelids and lower lash line. Start at your lash line, then work the shadow up to your crease. Next, blend the shadow up past your crease and towards your brows. Apply some shadow to your lower lash line too. Don’t worry about being too perfect here. You can use a cream-based theatrical makeup or regular eyeshadow, like what you’d buy from the makeup counter. If you’re doing the 1990 version of Pennywise, apply blue eyeshadow over your eyelid in a triangle shape instead.
Contour your jaw, mouth, temples, and chin with gray or black eyeshadow. Use a small brush to apply the shadow to the bottom corners of your mouth and the creases around your nostrils. Use a medium-sized brush to outline your jawline and chin, and a large brush to add depth to your temples. To get a more accurate look, tilt your chin down first, so that you have a double-chin, then apply the shadow to the crease between your chins. For a frowny look, apply a touch of gray eyeshadow under the inner corners of your eyebrows using a small brush. Skip this step and the next if you’re doing the original version of Pennywise from the 1990 film.
Splatter black water-based makeup over your the front of your bald cap. Dilute some black water-based makeup with water, then dip an old toothbrush into it. Hold the toothbrush over your bald cap, then drag your finger across the bristles. Start at the wig’s hairline and work your way down to where the bald cap ends. You can also use black hairspray or a stipple sponge, like what you’d use to paint a beard on. Water-based costume makeup would be the best, but you can use face paint too.
Draw on the eyebrows, then add creases between them. Pull out some reference pictures for the 2017 version of Pennywise. Use an angled lipstick brush and black eyeshadow to draw on the eyebrows, then add the eyebrow creases between them with gray oil-based makeup. An oil-based eyeshadow will work the best, but you can try regular eyeshadow too. An eyeliner or lip liner will also work. The creases between Pennywise's eyebrows look a little like parentheses. For the Tim Curry version, make the eyebrows smaller, darker, and less arched.
Finishing the Look
Enhance your eyes with black eyeliner. Apply the eyeliner to your upper and lower lash lines. You can use an eyeliner pencil or liquid eyeliner. For a darker look, apply eyeliner pencil directly to your waterline. Take a moment to enhance the shadows you added around your mouth and under your eyes. This is only for the 2017 version, however.
Paint your nostrils and the tip of your nose dark red. Use a lipstick brush to apply dark red makeup to the sides of your nostrils and the tip of your nose. Be sure to apply the makeup to the underside of your nose as well. Use reference photos from the 2017 film to ensure that you get the right shape. Oil-based face paint will work the best for this, but you can use lipstick too. For a more accurate look, lightly brush or "feather" the red paint up the bridge of your nose by about ⁄2 cm (0.20 in). If you want to do the Tim Curry version, pop on a rubber or latex clown nose. Do not use a foam clown nose; it’s too round.
Apply the same dark red color to your upper and lower lip. Use an angled lipstick brush to outline your upper lip just inside the lip line, and your bottom lip just outside the lip line. Fill your lips in inside these lines with the same color and brush. For the Tim Curry Pennywise, make both the top and bottom lips just inside your natural lip line.
Use an angled lipstick brush to apply the red face lines. Begin drawing a straight, vertical line above your drawn-on eyebrow. Skip past your eyelid, and continue drawing the line under your eye, curving it outward around your cheek. Finish the line by curving it into the outer corner of your mouth. Do this twice, once for each side of your face. Pull out some reference photos of the 2017 version of Pennywise for this. If you're doing the original 1990 Pennywise, draw a small, vertical black line under the center of each eye. They should only be about ⁄4 to ⁄2 in (0.64 to 1.27 cm) long.
Set your look with setting powder or setting spray. Apply a generous amount of setting powder with a powder brush, focusing on your nose and red lines. Wait 10 to 15 minutes, then dust it off with the powder brush. This is known as "baking" and helps your makeup last longer. Alternatively, apply a misting of setting spray instead. For best results, use theatrical-grade setting powder or setting spray. It will help your makeup last much longer!
Add some teeth prosthetics and contacts, if desired. This is not absolutely necessary, but it can really give your character a boost! For the 2017 version of Pennywise, you’ll need yellow contacts and a pair of sharp, pointy buck teeth. You can buy the contacts online and the teeth online or in a costume shop. Once you've completed the makeup, tilt your chin down, look up with your eyes, and give a nice smile. Skip this step if you’re doing the Tim Curry version. You could, however, pull on a pair of claw-like finger gloves. Remember to take all precautions when buying and wearing contacts. Get a prescription first, and never leave them in longer than a few hours.
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