Simon and Jeanette are a gift for any duo, couples, best friends or siblings, because the whole pairing rests on two colors and two pairs of glasses. They're the brainy ones of their groups, Simon in blue and Jeanette in purple, so everyday clothes in those shades already do most of the work. You can stay close to the animated outfits or go modern with sweaters, skirts, jeans and sneakers. What turns the clothes into a costume is small: chipmunk ears, a furry tail, neat hair and a bookish prop. Below are casual, preppy, dressy, sporty and last-minute versions for different ages and comfort levels.
Why the Glasses Matter More Than the Ears
Plenty of costumes have chipmunk ears. What makes people say Simon and Jeanette is the round frames on both of you, in blue and purple, so I sort those out first.
- If you already wear prescription glasses, round frames you own will do. Otherwise lens-free costume frames are easier on the eyes than cheap lenses, which can blur your view and fog up indoors.
- Keep both pairs the same shape and roughly the same size. Two different frame styles weaken the pairing more than people expect.
- Put the ear headband on before the glasses, so the arms of the frames sit over the band and nothing presses behind your ears all evening.
- Match shades on purpose. A cobalt or royal blue for him and a clear, bright purple for her keep the two apart; navy and plum next to each other can both read as dark in party lighting.
1. Classic Simon And Jeanette Costume
If you only make one version, make this one. Simon wears a royal blue turtleneck or oversized sweatshirt with straight-leg jeans and blue-and-white sneakers, plus round blue glasses, brown ears and a furry tail. Jeanette wears a purple sweater dress, lavender tights and purple flats or ankle boots, with round purple glasses, ears, a tail and long brunette hair tied back with a purple ribbon. Rosy cheeks, brown liner and a small painted nose are all the makeup it needs. Books or a light science prop say clever without a word. Brown gloves make subtle paws and keep hands warm on a cool night.
2. DIY Simon And Jeanette Costume
Open the closet before you buy anything, because this pair is mostly basics. Simon needs a blue hoodie, medium-wash jeans, sneakers and inexpensive round glasses. Jeanette layers a purple cardigan over a lavender T-shirt with a plaid skirt, tights and slip-on shoes. Brown felt ears glued to plain headbands take minutes, and tails are long tubes of brown fleece stuffed with fiberfill and pinned to belts. Fleece is my choice here because it doesn't fray and needs no hemming. Neat hair for him, a low ponytail or waves for her, and a little brown makeup at the nose and cheeks. Handmade name badges, pencils and notebooks clarify who's who without a full animal suit.
3. Last-Minute Simon And Jeanette Costume
Short on time? The color contrast carries this one. Simon pairs any blue sweatshirt with jeans, white sneakers, round glasses and a paper-ear headband. Jeanette wears a purple top with a skirt or leggings, purple shoes and round fashion glasses. Cut two tails from brown felt or poster board and fasten them firmly to the back of each waistband; poster board creases the first time you sit, so felt is the better quick option. Give Simon a tidy side part and Jeanette a purple scrunchie. Tiny brown noses in face-safe makeup and a few whisker dots, rather than long whiskers that smudge. A calculator and a stack of books are the props, and the blue and purple read clearly from across a room.
4. 1980s Simon And Jeanette Costume
The eighties version leans into the cartoon era the characters came from. Simon tucks a bright blue turtleneck into high-waisted jeans with white high-tops and oversized round glasses. Jeanette wears a purple sweater dress with a wide belt, opaque tights and low purple pumps, with big brunette hair held by a lavender bow. Both add brown ears and fluffy striped tails. Teasing hair for volume tangles it badly, so brush it through with conditioner the next morning before washing. Rosy cheeks and painted noses keep the faces animated without heavy makeup. Cardboard microphones or cassette-player props suit a retro party or a decade night.
5. Modern Simon And Jeanette Costume
A modern take can look like a party outfit and still keep every clue. Simon wears a cobalt knit sweater, black tapered jeans, white sneakers and slim round blue glasses. Jeanette wears a lilac cropped cardigan over a fitted purple midi dress, ankle boots and purple frames. Small brown ear headbands and sleek tails in matching shades stay discreet. The risk with a refined version is that it reads as two people in blue and purple, so don't drop the ears, whatever else you simplify. Combed hair for him, a polished ponytail with a velvet bow for her, natural makeup with tiny brown noses. A tablet or science notebook and a stack of color-coordinated books.
6. Simon And Jeanette School Costume
School uniform pieces suit these two well. Simon wears a blue sweater vest over a white button-down with navy chinos, loafers and blue round glasses. Jeanette wears a purple cardigan, a white collared blouse, a plaid knee-length skirt, lavender knee socks and loafers. Brown ears and soft tails attached firmly at the waist finish both. A geometry set for Simon and a binder with colored tabs for Jeanette. Side-part his hair, and put hers in a low ponytail with a purple ribbon. Keep makeup to rosy cheeks and small noses. It's a pairing teachers can wear to a school event without anyone raising an eyebrow, since it's essentially a uniform with ears.
7. Simon And Jeanette Nerd Costume
Exaggerating the nerdy side is half the fun. Simon tucks a blue sweater into belted khakis with patterned socks, loafers, oversized round glasses, a bow tie and a row of pencils in the shirt pocket. Jeanette wears a purple sweater vest over a white blouse, a pleated midi skirt, knee socks and purple Mary Janes, with round purple glasses and a thick book. A real encyclopedia gets heavy after an hour; a cardboard one painted to match is kinder to the arm. Ears, tails and painted noses tie it to the chipmunks. Flattened hair for him and slightly tousled pigtails for her, plus calculator watches and science-club badges, all easy to thrift.
8. Simon And Jeanette Science Fair Costume
A science-fair team gives the pair a story and something to hold in photos. Simon layers a short white lab coat over a blue turtleneck and dark jeans with supportive sneakers. Jeanette wears a lab coat over a purple blouse and knee-length skirt with lavender tights and closed-toe flats. A white coat can swallow all the color, so leave it open and let the blue and purple show down the front. Round glasses, ears, tails and painted noses for both. Safety goggles, clipboards, empty plastic test tubes or a cardboard solar system make good props, but no real chemicals or glass. A neat part for him, a loose ponytail with a purple bow for her.
9. Simon And Jeanette Library Costume
The library version is all soft layers and quiet detail. Simon wears a blue cable-knit cardigan over a pale blue shirt with corduroy trousers, loafers and round glasses. Jeanette wears a lavender cardigan over a purple midi dress, opaque tights and flat ankle boots. Ears, tails and a touch of brown nose makeup for both. Simon carries a few light books tied with ribbon; Jeanette carries a small book tote. Neat hair for him, loose brunette waves and a purple headband for her. Knits and corduroy are warm, so this suits cooler October nights, indoor parties and classroom celebrations rather than a crowded, hot dance floor.
10. Simon And Jeanette Preppy Costume
Crisp collars and matched colors give the preppy pair a sharp, put-together finish. Simon wears a blue quarter-zip over a striped button-down with tailored chinos, loafers and blue round glasses. Jeanette layers a purple cardigan over a white blouse and plaid A-line skirt, with knee socks and polished Mary Janes. Medium-length furry tails and ear headbands keep the chipmunk theme. When plaid is involved, I check the tones before anything else: pick a plaid where purple dominates, or Jeanette starts to look like a schoolgirl rather than a chipmunk. A navy book bag for him, a lavender satchel for her, a velvet ribbon in her hair, plus blush, a tiny nose and whisker dots.
11. Simon And Jeanette Varsity Costume
The varsity makeover keeps the brainy duo but gives them a sporty campus feel. Simon wears a blue varsity jacket over a white T-shirt with straight jeans and blue high-tops. Jeanette wears a purple varsity jacket, a pleated tennis skirt, white crew socks and purple sneakers. Round glasses, ears and fluffy tails for both. Felt initials on the jackets, S and J, work far better than any team logo, and stitching them on stops the corners curling. A notebook or foam pennant for Simon, a purple backpack for Jeanette. Clean side part for him, high ponytail with a purple ribbon for her, rosy cheeks and small noses.
12. Simon And Jeanette College Costume
Picture the two heading across campus in relaxed college clothes. Simon wears a roomy blue university-style sweatshirt, light-wash jeans, white sneakers and round blue glasses. Jeanette wears an oversized purple sweatshirt with a plaid skirt, bike shorts underneath, crew socks and casual sneakers. The ears and tails are what keep oversized sweats from looking like an ordinary day, so make the tails a little fuller than you think. Simon carries a laptop sleeve and a rolled poster; Jeanette carries a notebook, water bottle and pencil case. Simple hair, blush and small painted noses. Comfortable enough for a long night of walking or dancing.
13. Simon And Jeanette Pajama Costume
Pajamas make comfort the joke. Simon wears a blue pajama set or blue flannel pants with a soft long-sleeve top, fuzzy slippers and his round glasses. Jeanette wears purple plaid pajamas, lavender slippers and purple frames. Brown ear headbands and plush tails for both, with the tails sitting high enough that nobody steps on them. A blue pillow for Simon, a purple book and a small stuffed chipmunk for Jeanette. A loose braid with a lavender ribbon for her, gently tousled hair for him. Slippers are fine indoors but slick on wet pavement, so pack sneakers if you're going anywhere outdoors. Good for pajama days and indoor family parties.
14. Simon And Jeanette Winter Costume
Cold weather calls for coats, and the trick is keeping the blue and purple on the outside. Simon wears a royal blue peacoat over a blue sweater, dark jeans, knit gloves and weatherproof boots. Jeanette wears a purple wool coat over a lavender sweater dress, thick tights, gloves and purple ankle boots. Put the brown ears over matching beanies or earmuffs. Tails attached at the waist vanish under a coat, so I fix them to the coat hem instead with a safety pin from the inside. Blue glasses and a striped scarf for Simon, purple glasses and a lavender scarf for Jeanette, plus rosy cheeks and brown noses. Fit for parades and long outdoor walks.
15. Simon And Jeanette Rainy Day Costume
A wet Halloween doesn't have to wreck the costume. Simon wears a blue raincoat over a blue sweater and cuffed jeans, with navy rain boots and round glasses. Jeanette pairs a purple raincoat with a lavender dress, opaque tights and purple rain boots. Brown ears go on waterproof headbands, and short faux-fur tails stay off the wet ground; a long tail soaks up puddle water like a wick. Compact umbrellas in matching colors. Simon keeps his combed hair under the hood, Jeanette wears a low braid with a purple ribbon. Water-resistant makeup for the small noses and cheeks. The strong color blocking still reads through rain and gray light.
16. Simon And Jeanette Concert Costume
The Chipmunks and Chipettes are singing groups, so a concert pair makes sense. Simon wears a fitted blue blazer over a black shirt, dark jeans and polished blue sneakers. Jeanette wears a purple sequined jacket over a lavender dress or matching top and skirt, with purple ankle boots. Both wear round glasses, ears and neatly shaped tails. Toy microphones without branding work, or make your own from painted cardboard tubes topped with foam balls. Sequin jackets shed sequins from the cuffs, so check the stitching and catch loose ones before the party. Styled hair for him, soft waves with a glitter clip for her, blush, shimmer and tiny noses. Built for karaoke nights and music themes.
17. Simon And Jeanette Pop Star Costume
The pop-star version uses sparkle carefully so the colors still lead. Simon wears a metallic blue bomber over a plain shirt with black slim pants, blue sneakers and tinted round glasses. Jeanette wears a purple sequin mini or knee-length dress, lavender tights and comfortable platform sneakers. Trim the ears and tails neatly so they sit with polished outfits rather than fighting them. Tinted lenses look great in photos but darken a dim room fast, so I'd keep Simon's tint light. A toy microphone for him, a headset prop or glitter songbook for her. Volume in his hair, a high ponytail with a purple bow for her, shimmer, blush and little brown noses.
18. Simon And Jeanette Red Carpet Costume
For a dressy party, take the pair to the red carpet. Simon wears a navy suit with a cobalt shirt, blue bow tie, black dress shoes and sleek round glasses. Jeanette wears a floor-length purple gown or a modest midi with comfortable block heels and purple frames. Slim ear headbands and faux-fur tails secured at the back stay discreet. A tail on a gown needs a hidden anchor, like a ribbon loop stitched inside the waist seam, or it slides around the hips all night. A tidy side part for him, soft curls with a jeweled clip for her, glowing skin, gentle blush and subtle nose details. A small trophy prop or matching invitations suit the scene.
19. Simon And Jeanette Homecoming Costume
Homecoming styling sits between school spirit and semi-formal. Simon wears a blue dress shirt under a navy sweater vest with tailored trousers, loafers and round blue glasses. Jeanette wears a knee-length purple fit-and-flare dress, a cropped cardigan, low block heels and purple glasses. Brown ears and fluffy tails go on firmly enough for dancing. A fabric boutonniere in blue for him and a small purple wrist corsage for her are a sweet touch, and fabric flowers don't wilt. Combed hair for Simon, a half-up style with a lavender bow for Jeanette, natural makeup, rosy cheeks and painted noses. Matching dance tickets or a school pennant make easy props.
20. Simon And Jeanette Prom Costume
Would Simon and Jeanette coordinate their prom colors? Of course they would. Simon wears a dark blue suit with a royal blue tie, white shirt, dress shoes, round glasses, ears and a tail. Jeanette wears a flowing purple prom dress with a modest neckline, comfortable heels, purple glasses, ears and a matching tail, with a lavender sash or hair ribbon tying her hair to the gown. Smooth formal hair for him, an elegant ponytail or soft updo for her. Light evening makeup with subtle brown noses. Ear headbands dig into an updo, so slide them in before you pin the hair, not after. Fabric corsages, a cardboard dance invitation and a photo-frame prop round out the romance.
21. Simon And Jeanette Halloween Party Costume
At a regular Halloween party you'll be standing, eating and talking for hours, so this version is built for socializing. Simon wears a blue hoodie under a denim jacket with black jeans, sneakers, round glasses, ears and a tail. Jeanette layers a purple cardigan over a lavender top and plaid skirt with opaque tights, ankle boots, purple glasses, ears and a tail. Simon carries a notebook marked with simple science symbols; Jeanette has a small purple book bag. Side part for him, loose ponytail for her, rosy cheeks, small noses and short whisker dots. Party rooms heat up fast, and both the jacket and cardigan come off without losing the colors.
22. Simon And Jeanette Hoodie Costume
Matching hoodies are the easiest way to wear this duo and the easiest to reuse later. Simon wears an oversized royal blue hoodie with relaxed jeans, blue sneakers and round blue glasses. Jeanette wears a purple hoodie with a pleated skirt or fitted jeans, lavender socks, purple sneakers and round purple glasses. Sew or clip brown felt ears straight onto the hoods, which means no headband to slip, and attach plush tails at the back of the waistbands. Clips are the better choice if you want the hoodies back as everyday clothes. A calculator or rolled homework sheet for Simon, a book and a pencil tucked behind Jeanette's ear. Two low pigtails for her, tiny noses and blush.
23. Simon And Jeanette Denim Costume
Denim gives a casual base that still looks planned. Simon wears a medium-wash denim jacket over a blue turtleneck with dark jeans, blue sneakers and his round glasses. Jeanette layers a cropped denim jacket over a purple blouse and plaid skirt, with lavender tights, ankle boots and purple frames. Denim is close to Simon's blue already, so I make sure Jeanette's purple pieces are bright enough to hold their own against it. Ears, tails, rosy cheeks and painted noses for both. A blue backpack of light notebooks for him, a purple crossbody and pencil case for her. A side part for Simon, a half-up style with a purple bow for Jeanette. Practical for walking or a night outdoors.
24. Simon And Jeanette Overalls Costume
Overalls make a young, playful version that's easy to thrift. Simon wears blue denim overalls over a royal blue long-sleeve shirt with round glasses and blue canvas sneakers. Jeanette wears a purple corduroy overall dress over a lavender blouse with tights, purple slip-ons and round purple glasses. Ears go on plain headbands, and the tails fasten behind the overall bib straps, where they sit higher and drag less than at a waistband. Pencils in his front pocket, a small notebook of science doodles for her. Combed hair for him, braided pigtails with purple ribbons for her, rosy cheeks, whisker dots and brown noses. A natural pick for kids and siblings.
25. Simon And Jeanette Plaid Costume
Plaid adds interest without losing the academic look, but only if you pick the right plaid. Simon wears a blue plaid button-down under a solid navy cardigan with chinos, loafers and blue glasses. Jeanette wears a purple plaid dress or a blouse and skirt, lavender tights, purple flats and matching frames. Choose plaids where blue or purple clearly dominates; a red-heavy tartan muddles the characters at once. Ears, medium tails and subtle nose makeup for both. A ruler and hardback for Simon, a binder tied with purple ribbon for Jeanette. Sleek hair for him, loose curls and a simple headband for her. Comfortable enough for a long day event.
26. Simon And Jeanette Skater Costume
The skater version gives the pair a loose, streetwear shape. Simon wears an oversized plain blue T-shirt over a long-sleeve top, loose jeans, blue skate shoes, round glasses, ears and a furry tail. Jeanette wears a purple sweatshirt, black cargo pants, purple skate shoes, glasses, ears and a tail. Blue and purple beanies can sit behind the ear headbands as long as the ears still stay put; test that before you leave. A light skateboard prop without branding for Simon, a sticker-covered notebook for Jeanette. Tousled hair for him, two low braids for her, rosy cheeks and small noses. Easy to move in all night.
27. Simon And Jeanette Sporty Costume
For a costume built around movement, go athletic. Simon wears a blue track jacket and joggers over a white T-shirt with blue running shoes and round glasses. Jeanette wears a purple zip-up with a lavender tennis skirt or joggers, white crew socks, purple sneakers and purple glasses. Ear headbands slide off during games, so I'd pick ones with small teeth on the inside or pin them with bobby pins. Fix the short tails firmly. A stopwatch and water bottle for Simon, a clipboard or foam relay baton for Jeanette. Hair pushed off his glasses, a high ponytail for her, and face-safe brown noses with rosy cheeks that won't run with sweat.
28. Simon And Jeanette Cheer Costume
A cheer version brings school spirit and a lot of energy. Simon wears a blue varsity sweater with white trim, athletic pants, white sneakers and round blue glasses. Jeanette wears a purple pleated cheer dress, or a modest top and matching skirt with shorts underneath, crew socks and supportive sneakers. Ears and furry tails for both. Felt initials or simple science symbols replace team logos. A light cardboard megaphone for Simon, purple-and-white pom-poms for Jeanette. Pom-poms shed fine strands everywhere, so give them a shake outdoors first. Neat hair for him, a high ponytail with a wide purple bow for her, rosy cheeks and little noses. Spirit week ready.
29. Simon And Jeanette Detective Costume
Detective clothes turn their brains into a game. Simon wears a blue sweater under a tan trench coat with dark trousers, loafers, round glasses, ears and a tail. Jeanette wears a purple blouse, a plaid midi skirt, a cropped trench, tights, ankle boots, purple glasses, ears and a tail. A tan trench covers a lot of color, so keep the sweater and blouse in their brightest shades and wear the coats open. A plastic magnifying glass and notebook for Simon, a folder of harmless puzzle clues for Jeanette. Parted hair for him, a low ponytail under a purple beret for her. At a party they can investigate missing candy or a misplaced book.
30. Simon And Jeanette Professor Costume
The professor pair is a clever choice for adults and teachers. Simon wears a blue sweater vest over a white shirt with a bow tie, tweed trousers, loafers and blue round glasses. Jeanette wears a purple cardigan over a patterned midi dress, opaque tights, sensible block heels and purple glasses. Ears and fluffy tails keep the animated link. A pointer and a stack of papers for Simon, a clipboard and colorful markers for Jeanette. Perfectly combed hair for him, a low bun with a lavender ribbon for her, subtle blush, brown noses and whisker dots. Tweed is heavy and warm, which is fine in a classroom and much less fine at a crowded house party.
31. Simon And Jeanette Book Character Costume
A storybook version suits book days and library programs. Simon wears a blue waistcoat over a pale shirt with dark trousers, lace-up shoes, round glasses, ears and a curled furry tail. Jeanette wears a purple pinafore over a puff-sleeve blouse, lavender tights, Mary Janes, purple glasses, ears and a matching tail. A curl in a tail holds best if you sew a length of pipe cleaner or soft wire into the seam, with the ends tucked well in. Simon carries an oversized cardboard book with blue covers, Jeanette a purple storybook decorated with stars. A vintage part for him, long brunette hair with a velvet bow for her, soft rosy makeup and small noses.
32. Simon And Jeanette Cute Costume
Soft colors and plush textures make the sweetest version. Simon wears a fuzzy blue sweater with relaxed jeans, blue-and-white sneakers, round glasses, plush ears and an extra-fluffy tail. Jeanette wears a lavender knit dress with a purple cardigan, cozy knee socks, Mary Janes, purple glasses, ears and a soft curled tail. Rosy cheeks, tiny noses and a few whisker dots. A blue notebook for him, a small plush acorn or fabric book for her. Fuzzy sweaters shed onto dark clothes and onto each other, so keep a lint roller in a pocket. Softly combed hair for him, loose curls with a lavender bow for her. Gentle enough for younger wearers.
33. Simon And Jeanette Glam Costume
Velvet and shimmer turn the duo into a glamorous party pair. Simon wears a deep blue velvet blazer over a satin shirt with black trousers, polished loafers, round glasses, ears and a sleek tail. Jeanette wears a purple velvet midi dress with a glittering belt, opaque tights, jeweled flats or block heels, purple glasses, ears and a neatly shaped tail. Velvet crushes where a tail is pinned, so attach it to the belt rather than through the fabric. A refined side part for him, glossy waves with a sparkling lavender clip for her, luminous skin, rosy cheeks, soft shimmer and small brown noses. A metallic blue notebook and a purple clutch keep the props practical.
34. Plus Size Simon And Jeanette Costume
Flexible layers make the plus-size version easy to adjust for different bodies. Simon wears a relaxed blue sweater or tunic-length hoodie with stretch jeans, supportive sneakers, round glasses, ears and an adjustable tail. Jeanette wears a purple wrap dress or long cardigan over a lavender top and comfortable skirt, with opaque tights, wide-fit ankle boots, purple glasses, ears and a firmly clipped tail. I'd put both tails on an adjustable strap rather than a fixed belt, so the fit stays right sitting or standing. Choose soft fabrics that let you sit, walk and dance without constant tugging. A notebook for him, a purple satchel for her, neat hair, a ponytail or loose curls, rosy cheeks and small noses.
35. Kids Simon And Jeanette Costume
For children, soft materials and secure pieces matter more than accuracy. Simon wears a blue sweatshirt with pull-on jeans, cushioned sneakers, flexible round glasses, felt ears and a short light tail. Jeanette wears a purple cardigan over a soft dress or T-shirt and skirt, with leggings, slip-on sneakers, purple glasses, ears and a short tail. Pop the lenses out of costume glasses for kids, or buy lens-free frames, so nothing distorts their view on steps. Skip sharp fasteners, long dragging fabric and props that block sight. A foam calculator for Simon, a light picture book for Jeanette, a side part and a soft purple bow, plus face-safe blush and tiny brown noses.
Sewing a Chipmunk Tail That Doesn't Droop
Almost every look here has a furry tail, and a limp tail hanging at the back of the knees is the most common way these costumes go wrong. Here's how I make one that holds its curve.
- Cut faux fur from the back with a craft knife or the tips of small scissors, slicing only the backing. Cutting straight through the pile chops the fibers and you'll find fluff everywhere for a week.
- Sew the tube with the fur side in, brushing the pile away from the seam as you go, then turn it right side out and pick any trapped fibers free with a pin.
- Stuff lightly with polyester fiberfill. Packed too tight, the tail turns into a stiff club that won't bend when you sit.
- For an upward curve, slide a pipe cleaner or a strip of soft wire along the seam inside, ends folded over and taped so nothing pokes through.
- Attach it with a wide loop that threads onto a belt. Safety pins through a dress or skirt let the tail swing sideways and pull at the fabric.
Brown fleece is a fine substitute if faux fur sheds too much for you or for someone with allergies. It won't look as fluffy, but it doesn't shed, it needs no hemming and it goes through the wash.
Blue, Purple and Two Pairs of Round Glasses
Every pairing above rests on the same few things: blue for Simon, purple for Jeanette, round glasses, brown ears and furry tails. Those establish the duo before you add a single prop. From there, hoodies and pajamas, uniforms, formalwear or party sparkle can follow your ages, tastes and plans for the night. Fix the tails carefully, wear shoes you can stand in and use only face-safe makeup. Books, calculators, microphones and science bits show off their clever side without making anything awkward to carry. Get the two colors right and the rest is the fun part, for Halloween, spirit week or any dress-up day.
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