Start here: skin safety
Makeup is the fun part, but your skin has to survive the night too. A few rules before anything else:
- Cosmetic-grade products only. Use makeup, face paint or temporary tattoos made for skin. Never use craft paint, acrylic paint or permanent marker on your face or body.
- Patch test the day before. Dab a small amount on the inside of your elbow or behind your ear and wait. If you see redness, itching or bumps, skip that product.
- Keep products out of the eyes. Stay away from the waterline, and skip glitter near the eyes entirely.
- Read the label. Some face paints are labeled for adults only or list ingredients to avoid. Follow the directions for use and removal.
The five o'clock shadow in five minutes
A light stubble shadow is the single best upgrade for a prisoner look. It says "long night" without much effort, and anyone can wear it.
- Start with clean, moisturized skin and let it settle for a minute.
- Dip a stipple sponge into a matte brown or gray eyeshadow or cream makeup a few shades darker than your skin. Tap the sponge on the back of your hand to remove most of it.
- Press, do not swipe, along the jawline, chin, upper lip and the lower cheeks. Lighter is better; you can always add more.
- Soften any hard edges with a clean finger, then set with a light dusting of translucent powder.
No stipple sponge? Tap a clean mascara spoolie lightly in the shadow and press it on. If you already have a beard, just leave it a little untidy and you are done.
Tired eyes and a "just booked" face
The mugshot look is all about looking like you have had a long day. Brush a little matte taupe or soft purple brown shadow under the eyes and blend it out so it looks like shadows, not makeup. Skip mascara and highlighter, and use a matte powder to take away shine. Messy brows brushed slightly up finish it off. Then practice the stare: chin level, mouth flat, eyes unimpressed.
Fake tattoos: neck, knuckles and forearms
Temporary tattoos are the easiest way to look tougher without anything permanent. A few placements that read well in photos:
- Knuckles: four letters on each hand is the classic. Try FULL on one hand and SIZE on the other for a candy joke, or BOO! on both.
- Neck: a small star, a spiderweb or a swallow just below the ear.
- Forearm: a heart with a banner that says MOM is a timeless, friendly choice.
Prefer to draw your own? Use a body safe eyeliner pencil, then set it with powder so it does not smudge. Keep designs playful and skip teardrops, gang symbols or real prison tattoo symbols, which carry real meanings.
Bruises and scuffs: keep it light
A little scuff can add story, but this is a prisoner costume, not a horror costume. Keep it subtle:
- Small bruise: tap a touch of purple on the cheekbone or brow bone, then a little red at the edges and a hint of yellow green around it. Blend with a finger so there are no hard lines.
- Dirt smudge: a swipe of matte brown eyeshadow on a forearm or cheek looks like you have been digging an escape tunnel with a spoon.
- Skip the gore. No fake blood or wounds for this look. It changes the vibe from funny to grim.
For kids, skip the bruises and keep only a tiny dirt smudge, if any.
Prisoner hair ideas
The messy bun
The "just rolled off the bunk" bun is easy and works with any costume. Flip your hair, twist it loosely on top of your head, secure it with an elastic and pull a few strands loose around your face. Dry shampoo or texture spray gives it grit.
Slicked back
Comb a strong hold gel straight back from the forehead for a vintage 1950s jailbird look. It pairs perfectly with black and white stripes and a striped cap.
The buzz cut cap look
For a shaved head look without the shave, wear a bald cap or a tight skin tone wig cap. Lightly stipple a little gray or brown eyeshadow over the cap for a buzzed stubble texture. Tuck longer hair into a thin wig cap first.
Bedhead
Short hair? Rub a little paste between your palms and scrunch it in every direction. Done in under a minute.
The glam mugshot look
Not every prisoner look has to be gritty. The glam mugshot is a favorite with women's prisoner costumes and fitted striped dresses: think "the party got out of hand." Go for a bold winged liner, a red or berry lip, defined brows and big soft waves or a high ponytail. Then smudge the outer corner of the liner just a little for the "long night" detail.
Hold a letter board sign with a silly charge and give the camera a confident half smile. More sign and charge ideas live in our prisoner costume accessories checklist.
Kid safe face paint options
Kids can join the fun with a much lighter touch. Pick a water based face paint labeled for use on skin, and patch test it the day before. A few easy ideas:
- Stubble dots: tap tiny brown dots along the chin and jaw with a damp sponge.
- Cheek number: paint a small 1031 on one cheek in black.
- Mini tattoo: a kid friendly temporary tattoo of a star or a skull on the back of the hand.
Skip glitter near the eyes and keep paint off the lips. Our kids prisoner costume guide covers costumes and props for little jailbirds.
Removing it all at the end of the night
Most makeup comes off with an oil based cleanser or makeup remover, followed by a gentle face wash. Face paint usually washes off with soap and water. Peel temporary tattoos with a little oil or rubbing gently with a damp cloth. Moisturize afterward, and do not sleep in it.
Put the whole look together
Makeup is the finishing touch, so start with the outfit. If you are still choosing, our orange jumpsuit vs stripes comparison helps you pick an era. Building it yourself? The DIY prisoner costume guide pairs well with the looks here, and the men's prisoner costume guide covers fit and picks. Doing a duo? A matching five o'clock shadow on both cellmates is a great touch for couples prisoner costumes.
Questions people ask
How do you do prisoner makeup?
Keep it simple: stipple a light five o'clock shadow with a sponge, add a little shadow under the eyes, and apply one or two temporary tattoos. Finish with messy or slicked back hair.
How do I fake a five o'clock shadow?
Dip a stipple sponge in a matte brown or gray eyeshadow or cream makeup, tap off the excess, and press it lightly along the jaw, chin and upper lip. Build it up slowly and set it with powder.
Can I draw fake tattoos with a permanent marker?
No. Markers are not made for skin and can irritate it or be hard to remove. Use temporary tattoos or a cosmetic eyeliner pencil instead, and patch test first.
What hairstyle goes with a prisoner costume?
A messy bun, slicked back hair or tousled bedhead all work. For a buzz cut look, wear a bald cap or a tight skin tone wig cap.
What prisoner makeup is safe for kids?
Use water based face paint labeled for use on skin, patch test it the day before, and keep it away from the eyes. A few stubble dots and a tiny painted number on the cheek are plenty.