Dorothy is one of the few costumes where a handful of small details do all the work: blue gingham, a white puff-sleeve blouse, two braids, red shoes and a basket with a little dog in it. When I style a Dorothy, I check those before anything else, and once they're right almost everything around them can change. Below are forty versions, from an outfit pulled from your own closet to glam party looks, decade twists and mashups with her travelling companions. Some are built for kids and toddlers, one for a bump, and a few for nights when you'll be outside in the cold. Each one covers the hair, makeup, shoes and accessories, so you can see the whole costume before you start gathering pieces.
Gingham, Braids and Red Shoes Do the Talking
When I style a Dorothy, I run through the same short checklist before anything else, because these are the things people read from across a room. Lose two of them and you start getting asked if you came as a milkmaid or a picnic.
- Blue-and-white gingham somewhere obvious, ideally on the dress or pinafore. A small to medium check reads as Dorothy; a big buffalo check reads as a lumberjack shirt or a tablecloth.
- A white layer at the top, usually a puff-sleeve blouse. It frames the face and keeps the check from sitting straight against your skin.
- Two braids with blue ribbon. They're the main reason people can guess the character from behind.
- Red shoes with some shine. Matte red can pass, but glitter or patent catches the light and makes the point for you.
- A basket, and better still a small dog in it.
Every idea in the list below, from the decade looks to the mashups, works because it keeps most of those intact. If you're adapting one, change the silhouette or the palette freely, but hold on to the check pattern and the red shoes until last.
Making Red Glitter Shoes That Don't Shed All Night
Store-bought costume shoes are often stiff and slippery, so I'd rather glitter a pair of flats or sneakers you already walk well in. Only do this to shoes you're happy to keep as Dorothy shoes, because the finish doesn't come off cleanly.
- Wipe the shoes with rubbing alcohol so the glue grips, and stuff them with paper to hold their shape.
- Brush on a thin coat of decoupage glue or a flexible fabric glue, one section at a time, and pour fine red glitter over it while it's wet. Tap the excess onto a sheet of paper and funnel it back into the jar.
- Let it dry, then add a second coat. Two thin coats look fuller than one thick one and crack less.
- Keep the layer thin across the toe crease where the shoe bends, since a heavy coat cracks and flakes there first.
- Seal with a clear spray sealer or a last layer of glue, and leave the shoes overnight before you wear them.
Glitter still travels, so expect a little on the car floor. For borrowed shoes, or anything you'd mind changing, red glitter shoe clips or sequin-fabric shoe covers held on with an elastic strap under the arch are the safer route.
1. Classic Dorothy Halloween Costume
This is the version I'd make first if you've never worn Dorothy before. A blue-and-white gingham pinafore goes over a crisp white blouse with short puff sleeves, and the skirt stops at the knee so you can walk and climb steps. White ankle socks and glittery red flats with a low heel or a strap finish the feet; strapless flats tend to slip off at the heel by the second hour. Part the hair in the center, braid each side neatly and tie off with pale blue ribbon. Rosy cheeks, mascara and a soft pink lip are all the makeup it needs. Line a small wicker basket with blue fabric for the plush terrier, and wear bloomers or fitted shorts underneath, because a full skirt flips up every time you sit on a curb.
2. Easy DIY Dorothy Halloween Costume
No sewing needed here. A fitted white T-shirt under a blue gingham sundress or checked apron dress you already own gets you most of the way. If the dress is plain blue, fold a square of gingham into an apron and tie it at the waist; from a few feet away nobody can tell it isn't part of the dress. I use removable glitter shoe clips on red ballet flats rather than gluing anything, so the shoes go back to normal on November first. White crew socks, two loose braids with blue ribbon, peach blush, brown mascara and tinted balm keep the rest simple. A reusable market basket with a small stuffed dog does the job of the wicker one, and the whole outfit still reads clearly in photos without costing much.
3. Glam Dorothy Halloween Costume
The glam version swaps the soft pinafore for a fitted gingham dress with a corset-style bodice, wide straps and a full midi skirt, worn over a white blouse with sheer puff sleeves and a high neck. Red rhinestone pumps carry the sparkle, and crystal-trimmed ankle socks add a second flash near the shoe. Glossy braided pigtails with velvet blue bows, luminous skin, fluttery lashes, champagne shadow and a classic red lip make it a party face. I'd trade the wicker basket for a small structured basket-shaped handbag, which holds your phone and doesn't snag tights. Red gemstone earrings finish it. One honest warning: boned bodices get uncomfortable after a big meal, so try it on sitting down before the night.
4. Vintage Kansas Dorothy Costume
Muting the colors turns this into the Dorothy from the farm, before the storm. A dusty blue gingham pinafore over an ivory cotton blouse with a rounded collar and gathered sleeves sets the tone, and a cream petticoat gives the skirt some lift. Brown lace-up boots replace the glitter shoes, so burgundy ribbons on two textured braids carry the red instead. Freckles, cream blush and a sheer berry lip suit the softer palette. Fill a weathered wicker basket with a checked cloth and the plush dog, and keep a beige cardigan nearby for outdoors. It's my pick for anyone who finds bright costume colors too loud, though without red shoes a few people will need a second look.
5. Modern Dorothy Halloween Costume
For a current take, I start with a blue gingham mini dress with clean lines, a square neckline and real side pockets, layered over a fitted white mock-neck top. White platform sneakers with removable red glitter laces keep the red-shoe signal while letting you walk for hours. Two low bubble braids with narrow blue ribbon look fresh, and brushed brows, soft brown liner, peach blush and a glossy red lip suit the shorter hem. Clip a plush terrier keychain to a small woven crossbody bag in place of the basket, then add silver hoops and white bike shorts underneath. The laces are the weak spot: they're thin, so pick the chunkiest glitter laces you can find or nobody will notice them.
6. Plus Size Dorothy Halloween Costume
Fit through the bodice decides whether this one is comfortable. I check that the gingham sits smooth without the straps digging in or the waist pulling, because a strained check pattern shows tension far more than a solid fabric does. An adjustable pinafore with a defined waistband, a roomy skirt and pockets solves most of that. Underneath, a breathable white blouse with elbow-length puff sleeves keeps arms covered without trapping heat. Soft ankle socks and cushioned red Mary Janes with wide straps handle a long evening. Two loose braids, blue satin bows, rosy makeup and a red lip finish the face. Add a crossbody strap to the basket if you want your hands free, and wear anti-chafe shorts and a light petticoat under the skirt.
7. Kids Dorothy Halloween Costume
Kids pull off anything itchy fast, so I put a soft white cotton T-shirt or leotard under the gingham jumper to keep seams off the skin. Secure straps and a knee-length skirt mean nothing drags on steps while trick-or-treating. Red glitter sneakers with white crew socks are safer than costume heels, which slide on wet leaves. Two comfortable braids with fabric bows instead of sharp clips, plus a little washable pink cheek color and lip balm, is all the beauty work a child needs. A lightweight foam basket with a plush puppy won't hurt anyone if it lands on toes. I also hide strips of reflective tape along the basket and the hem so drivers can see them after dark.
8. Toddler Dorothy Halloween Costume
With a toddler, comfort and diaper changes come before accuracy. A cotton gingham romper with an attached skirt and snap closures, over a white puff-sleeve top, gives the Dorothy shape without a separate dress riding up. Red nonslip shoes or flexible glitter sneakers are kinder to new walkers than hard dress shoes. Choose white socks with gentle elastic so they stay up without marking the leg. If there's enough hair, two tiny pigtails with soft blue fabric ties look sweet; if not, a soft blue bow headband does the same job. I skip face makeup entirely at this age. Attach the plush puppy firmly to a small fabric basket, and bring a blue cardigan for cool evenings and stroller rides.
9. Teen Dorothy Halloween Costume
Teens usually want Dorothy to look like an outfit first and a costume second, and this one manages both. A blue gingham fit-and-flare dress with a square neckline goes over a cropped white blouse that meets the waistband, so nothing shows when they lift their arms. White crew socks with red platform sneakers or low block-heel Mary Janes keep it walkable. Loose braided pigtails with a few face-framing pieces, winged brown liner, pink blush, a touch of highlighter and a glossy red tint suit that age. A compact woven bag with a small plush dog charm replaces the big basket. Bike shorts under the skirt and a light blue cardigan make it fine for school events.
10. Maternity Dorothy Halloween Costume
An empire-waist gingham dress that falls over the bump is the starting point, with a white stretch-knit top underneath for the puff-sleeve layer. Stretch matters more than you'd think: buttoned blouses gape across a changing chest, and knit doesn't. Red cushioned flats or supportive sneakers with white ankle socks make standing at a party easier on tired feet. Two relaxed side braids with blue bows, or a single braided crown if pigtails feel awkward, keep the hair in character. Hydrating foundation, cream blush, mascara and a tinted red balm stay comfortable all evening. Carry a light fabric basket with the plush terrier instead of heavy wicker, and tie a gingham belt above the bump for shape without pressure.
11. Cold Weather Dorothy Costume
Late October can be properly cold, and the trick is warmth that doesn't bury the gingham. I put a long-sleeve white thermal under a pinafore in heavier cotton or brushed flannel, then fleece-lined white tights and red ankle boots with nonslip soles. A blue wool cardigan or cropped peacoat sits over the dress without hiding the checks, as long as you leave it open. Two secure braids with velvet ribbon hold up under a hat brim. Cold air dries makeup out, so cream blush, waterproof mascara and berry balm hold better than powder. Line a sturdy basket with a small blue blanket for the plush dog, and add red gloves as one more spot of the signature color.
12. Warm Weather Dorothy Costume
For a warm-climate Halloween I go for a sleeveless blue gingham sundress in breathable cotton or linen, with wide straps, a flexible bodice and an airy knee-length skirt. A light white camisole underneath gives the layered look without full sleeves holding heat. Red canvas sneakers and thin ankle socks keep feet cool. Lift two loose braids slightly away from the neck so they aren't lying on damp skin. Sunscreen, waterproof mascara, peach blush and a red lip stain survive the heat far better than heavy foundation. A small open-weave basket with a plush puppy finishes it. Leave out the petticoat and any wig; both turn a hot evening into an endurance test.
13. Modest Dorothy Halloween Costume
This version adds coverage without losing the blue and white. A calf-length gingham pinafore with a full skirt goes over a high-neck white blouse with long puff sleeves, and opaque white tights carry the coverage down to red low-heeled Mary Janes or polished red loafers. Two tidy braids with blue grosgrain ribbon, rosy cheeks, defined lashes and a muted red lip keep the face soft. The wicker basket holds a folded blue cloth and the plush dog. One detail I never skip here is a white slip, because thin gingham turns see-through under bright party or stage lighting. It fits school, work and family events where a short hem wouldn't go down well.
14. Dorothy Costume With Red Sneakers
Swapping dress shoes for bright red sneakers is the biggest comfort upgrade you can make to this costume. The rest stays classic: a blue gingham pinafore, a white short-sleeve blouse and ruffled white ankle socks. Temporary glitter laces or detachable red bows add sparkle to plain sneakers without wrecking them. Braided pigtails with blue ribbon, rosy blush, mascara and a red lip stain that won't need constant touch-ups keep the face easy. A wicker-look backpack frees both hands, with the plush terrier attached on the outside where people can see it. Wear white bike shorts underneath and you can handle a long party, a theme park day or a whole neighborhood route.
15. Dorothy Tutu Costume
A tulle skirt makes this one move, which kids and dancers love. Pair a white puff-sleeve leotard with a layered blue tulle skirt, then tie a gingham apron panel over the top so the print still shows. Fitted shorts under the tutu keep everyone comfortable. Red glitter ballet flats or red dance sneakers go with white ankle socks. Oversized blue bows on two braided pigtails, pink cheeks, curled lashes and a glossy red lip suit the playful shape. Carry a light fabric basket with the plush puppy, and add a small gingham bow at the waist to tie the separate pieces together. Tulle crushes when it's sat on in a car, so put the skirt on when you arrive if you can.
16. Dorothy Pants Costume
You don't need a skirt to be Dorothy. High-waisted blue gingham trousers with a white puff-sleeve blouse and matching gingham suspenders give the pinafore lines in a different shape. I keep the leg slightly cropped or tapered so the red glitter loafers stay visible; a full-length wide leg hides the shoes, and the shoes carry half the character. White socks, braided pigtails and blue ribbon keep the familiar signals. Rosy cheeks, brown liner and a red lip finish the face. A structured wicker handbag with a plush terrier peeking out, and a red belt linking the shoes and lipstick, pull it together. It's the one I suggest for work parties, cycling or anyone who simply lives in trousers.
17. Dorothy Overalls Costume
Overalls read as a pinafore with legs, which is why this casual version works. Layer a fitted white puff-sleeve blouse under full-length gingham overalls and roll the cuffs a little so the white socks show. Red canvas sneakers with sparkly laces give you the signature shoe in comfort. Part your hair down the center for two relaxed braids with blue ribbon, and keep makeup light: foundation, pink cream blush, mascara and a red tinted balm. A small wicker basket or woven backpack holds the plush dog. Plain denim overalls work too if you add gingham patches to the bib and pockets; I'd pin them for a one-night costume and sew them if you plan to wear the overalls again.
18. Denim Dorothy Halloween Costume
Denim instead of gingham is the subtle route, and it depends on everything else being right. A blue denim pinafore over a white eyelet blouse keeps the farmhouse feel, with white ankle socks and glittery red flats. Tie narrow blue ribbon around two softly pulled-apart braids. Light makeup with rosy blush, brown mascara and a satin red lip suits it. Line a natural wicker basket with blue checked fabric so the print appears somewhere, with the plush terrier peeking over the edge. If people still look puzzled, add gingham buttons, pocket trim or a removable apron panel. The denim takes outdoor wear without complaint and goes straight back into your everyday clothes afterward.
19. Dorothy Gingham Jumpsuit Costume
A gingham jumpsuit gives a sharper outline while keeping the print that defines the character. I'd choose a sleeveless style with wide legs, a fitted waist and adjustable straps, so you can shorten the straps if the crotch hangs low. Layer a white puff-sleeve blouse underneath and wear red platforms or supportive red wedges. Polished pigtail braids with small blue bows, fresh skin, rosy cheeks, soft lashes and a red lip keep the face classic. A compact wicker handbag with a tiny plush dog replaces the basket. A narrow white belt brightens the waist and red studs echo the shoes. It suits adults who'll be dancing and want something less expected than the full skirt, though bathroom trips take longer.
20. Cottagecore Dorothy Costume
Soft textures and handmade touches pull Dorothy into cottagecore. A blue gingham midi pinafore goes over an ivory blouse with lace-trimmed puff sleeves, a cotton petticoat adds fullness, and white ribbed socks sit under red leather Mary Janes with a low heel. I weave narrow blue ribbon right through the loose braids instead of tying it at the ends, and leave a few natural curls free at the face. Freckles, peach blush, brushed brows and a sheer berry lip fit the mood. Fill the wicker basket with a checked napkin, faux wildflowers and the plush terrier, and pin a small gingham bow at the neckline. Keep the flowers low in the basket, or the dog disappears behind them.
21. Western Dorothy Halloween Costume
This one blends the gingham with friendly Western details. A gingham shirt dress with a flared knee-length skirt and a white yoke or collar is the base, and bright red cowboy boots take over from the sparkly flats, with white ruffled socks showing above the boot tops. Two braids sit under a small white cowboy hat trimmed with blue ribbon. Warm blush, brown mascara, light freckles and a red balm give a sun-kissed face. Tie a blue bandana around the handle of a woven basket holding the plush dog, and add a red belt with a simple silver buckle. New cowboy boots are stiff, so wear them around the house for a few evenings before Halloween.
22. 1950s Dorothy Costume
A full circle skirt gives this version its 1950s shape. Choose a blue gingham shirt dress with a fitted waist, white collar and short cuffed sleeves, and put a white petticoat under it for volume. White ankle socks with red kitten heels or Mary Janes fit the period and are easy to find. Two smooth braids or curled pigtails with blue bows both suit the decade. Softly winged liner, defined lashes, pink cheeks and a classic red lip finish the face. Carry a structured wicker handbag with a plush terrier tucked inside, and add small pearl studs and a narrow red belt. Stiff net petticoats scratch bare legs, so I'd pick a soft one or wear sheer tights.
23. 1970s Dorothy Costume
The 1970s take breaks the pinafore into separates: blue gingham flared pants, a white blouse with billowy sleeves and a fitted gingham vest on top. Red platform clogs bring height and color, and white socks soften them. Two loose, slightly undone braids with faded blue ribbon match the decade better than tight neat ones. Warm neutral shadow, peach blush, separated lashes and a brick-red lip suit the palette. A rounded woven bag with a plush terrier charm replaces the formal basket, and a blue neck scarf with daisy earrings adds the period details. Clogs are slippery on smooth floors, so scuff the soles with sandpaper before you head out.
24. 1980s Dorothy Costume
Turn the volume up with a bright gingham skater dress that has puffed shoulders, a fitted waist and a full skirt. A white ruffled blouse goes underneath and a wide red belt cinches the middle. White slouch socks with red high-top sneakers and glitter laces handle a night of dancing. Pull two high braided pigtails up with oversized blue scrunchies. Blue eyeliner, rosy blush, glossy red lips and softly defined brows look right for the era. A boxy wicker handbag with the plush dog clipped to the handle and red plastic earrings finish it. The shoulders and scrunchies already shout 1980s, so I keep everything else plain to stop it tipping into a different character.
25. 1990s Dorothy Costume
The 1990s version is a gingham slip dress over a fitted white baby tee, with white crew socks and chunky red sneakers or platform Mary Janes. Two low braids and a few small blue butterfly clips near the part do most of the decade work. Brown pencil liner, matte skin, muted blush and a deep red lip stain keep the face understated. A mini woven backpack with a small plush terrier poking out of the top stands in for the basket. A blue choker and silver hoops add period detail without stealing focus. Slip dresses tend to cling, so fitted shorts underneath help it hang cleanly as well as keeping you covered.
26. Y2K Dorothy Halloween Costume
A Y2K Dorothy leans shiny and young. A blue gingham mini dress goes over a fitted white top with mesh sleeves, with white knee socks and red platform sneakers. I'd pick footwear with glitter or metallic accents over an extreme heel; tall platforms and trick-or-treating curbs don't mix. Two mini braids feeding into low pigtails, with blue star clips, set the era. Frosted blue shadow, glossy red lips, pink blush and a little face shimmer suit it. A small woven shoulder bag with a plush puppy keychain replaces the basket. Red-tinted sunglasses and a silver heart necklace add early-2000s energy, and the gingham and red shoes keep it Dorothy.
27. Punk Dorothy Halloween Costume
Punk Dorothy gets her edge from texture, not from anything graphic. Layer a gingham pinafore with decorative safety-pin closures over a white band T-shirt or puff-sleeve blouse, and add black-and-white striped tights with red lace-up ankle boots that have glitter panels. Weave blue and red ribbon through two textured braids. Smudged black liner, strong brows, rosy cheeks and a deep red lip carry the attitude. Decorate the wicker basket with removable plaid patches next to the plush terrier, and throw on a cropped denim jacket for warmth. Use costume-safe plastic hardware rather than real metal spikes; real ones catch on sweaters and scratch whoever you hug.
28. Gothic Dorothy Halloween Costume
Deeper shades turn Dorothy gothic without making her frightening. A navy-and-white gingham pinafore over a high-neck white blouse with lace sleeves sets the tone, with opaque white or gray tights and dark ruby velvet Mary Janes. Two long sleek braids with navy bows suit the palette. Pale matte foundation, smoky gray shadow, defined lashes, burgundy blush and dark red lipstick give the mood. Paint a wicker basket charcoal and fill it with a black plush terrier and a folded blue cloth. A fitted navy capelet adds warmth and a little drama while leaving the dress visible. Velvet shoes mark easily on wet pavement, so I'd save this one for an indoor party.
29. Pastel Dorothy Halloween Costume
Pastels make this outfit light and dreamy. A pale blue gingham pinafore over a white blouse with sheer puff sleeves and ruffled cuffs, plus white ankle socks and blush-red or rose-pink glitter flats, set the palette. Powder-blue satin bows on two loose braids, pastel blue shadow, pink cream blush, curled lashes and glossy rose lips keep it soft. A whitewashed wicker basket holds a cream plush puppy and a folded gingham cloth, and cloud or star earrings suit the storybook feel. The risk with pastels is that pale pink shoes stop reading as Dorothy's shoes, so I push the shoes toward the red end of that range. Done that way, it suits adults, teens and coordinated groups at daytime events.
30. Rainbow Dorothy Halloween Costume
This version nods to the color of the journey with rainbow trim on the classic outfit. Start with a blue gingham pinafore and white puff-sleeve blouse, then run narrow rainbow ribbon around the hem, the waistband and the basket handle. Red glitter sneakers with white ankle socks keep it comfortable. Braids tied with multicolored ribbon look fun, but I keep blue as the main ribbon so the hair still matches the dress. Soft rainbow liner, pink blush, mascara and a glossy red lip finish the face. The basket holds a plush dog and a small fabric rainbow. Resist adding color to the dress itself; the blue, white and red base is what tells people who you are.
31. Dorothy Scarecrow Mashup Costume
Here Dorothy borrows from her straw-stuffed friend. A gingham pinafore goes over a cream plaid shirt with straw-colored fringe at the cuffs, plus patched blue leggings or tights and red lace-up boots. Two braids sit under a floppy brown hat with a blue ribbon band. Painted freckles, rosy cheeks and a few stitched lines drawn around the mouth with brown face pencil give the scarecrow hint without heavy makeup. Tuck a little faux straw around the edge of the basket beside the plush terrier, and sew fabric patches onto the skirt to tie the two characters together. Real straw sheds everywhere and pokes through fabric, which is why I stick to raffia or fringe trim.
32. Dorothy Tin Traveler Mashup Costume
Metallic accents merge Dorothy with a friendly tin-inspired traveler. Wear a checked pinafore over a white blouse with silver cuffs and a small metallic collar, then silver leggings under the skirt and red glitter ankle boots. Two sleek braids get silver and blue ribbon. Cool gray shadow, silver liner, rosy cheeks and red lipstick suit the mix. A lightweight silver-painted basket holds the plush dog and a small decorative heart. The funnel hat is where I'd spend the effort: soft craft foam rolled into a cone stays light, and a thin elastic under the hair keeps it from sliding forward. Metallic leggings run hot, so test them in a warm room first.
33. Dorothy Lion Mashup Costume
Golden details blend Dorothy with her brave lion companion. A blue gingham pinafore over a tan puff-sleeve blouse, with caramel tights and red Mary Janes, sets the warm palette. Add a faux-fur ear headband over the two braids and a small golden mane collar at the neckline. Bronze shadow, a brown button nose, whisker dots, peach blush and a red tinted balm make a friendly face. Tie golden ribbon around the basket handle next to the plush terrier, and pin a detachable faux-fur tail to the back of the dress. Faux fur sheds badly when cut with long scissor strokes, so I snip only the backing from behind with small cuts and shake the pieces outside before wearing them.
34. Dorothy Good Witch Mashup Costume
This one adds fairytale sparkle to the gingham. A pale blue gingham midi dress with a fitted bodice, full skirt and sheer white puff sleeves sits under a translucent pink capelet, with white ankle socks and red glitter flats. Two soft braids go beneath a small silver star crown, with blue ribbon at the ends. Pearly shadow, pink blush, a little face shimmer, defined lashes and a rose-red lip match the shine. The basket holds a plush puppy and a light foam star wand. Tall crowns slide backward on braided hair, so I keep this one low and anchor it with two bobby pins crossed in an X on each side.
35. Dorothy Wicked Witch Mashup Costume
Black and green details give the cheerful dress a mischievous turn. A gingham pinafore goes over a fitted black puff-sleeve blouse, with black tights and deep red ankle boots. Two long braids sit under a small black pointed hat trimmed with blue ribbon. I use green eyeliner instead of full green face paint, which rubs onto collars and takes real effort to remove; pair it with smoky shadow, rosy cheeks and dark red lipstick. A black wicker basket holds the plush terrier and a striped cloth, and a light black cape comes off indoors. Green earrings or nail polish echo the liner. It stays playful enough for any public party.
36. Dorothy Tornado Costume
This idea turns the journey itself into the costume. The classic base of gingham dress, white blouse, white socks and red glitter sneakers stays underneath, and gray tulle wraps around the waist and shoulders in soft spiral bands. Tiny foam clouds and miniature lightweight house shapes ride on the tulle. Wind-tossed braided pigtails with blue bows, gray-blue shadow, pink blush and red lipstick finish the face. Secure the plush dog inside a small basket so it doesn't fly off. I tack the tulle at a few points with needle and thread rather than glue, because hot glue goes stiff and pops off once you start moving. It also gets through a doorway far more easily than a cardboard tornado.
37. Emerald City Dorothy Costume
Green accents show that Dorothy has reached the city at the end of the road. Keep the classic gingham pinafore and white puff-sleeve blouse, then add an emerald cropped cape or sequined cardigan. Red glitter shoes and white ankle socks hold the core colors. Twist blue and green ribbon together through two braids. Green shimmer liner, luminous skin, rosy cheeks and red lipstick suit the mix. A green-painted basket holds the plush terrier and a pair of green-tinted glasses, a nod to the spectacles everyone wears in the city in the book. Emerald earrings and a narrow green belt tie the new color in. Sequins scratch bare arms, so the cape is the gentler pick over a short-sleeved blouse.
38. Pop Art Dorothy Halloween Costume
Bold outlines and graphic makeup give this Dorothy a comic-book look. A bright gingham dress over a crisp white blouse gets its seams traced with removable black fabric ribbon, with white ankle socks and shiny red block heels. Shape two neat braids and secure them with vivid blue bows. A fine makeup pencil draws clean black outlines on the face, with small white or blue cosmetic dots across the cheeks, a bright red lip and defined lashes. Outline the wicker basket and its plush terrier's corner with black ribbon too, so it matches. Pencil lines smudge first around the mouth and nose, so I set them with translucent powder and carry the pencil for touch-ups. It reads strongly in bright light and needs no mask.
39. Ghostly Dorothy Halloween Costume
For a gentle spooky version, I fade the colors rather than adding anything gruesome. A pale blue-and-gray gingham pinafore over an ivory blouse with fluttering sheer sleeves sets the tone, with light gray tights and muted ruby flats dusted with fabric-safe shimmer. Loose, slightly wispy braids with faded blue ribbon look weathered. Cool-toned foundation, gray shadow, soft pink blush, silvery highlight and a blurred berry lip keep the face pale but alive. A whitewashed basket holds a gray plush puppy and a scrap of gauze, and a translucent gray cape floats behind you as you walk. Pale gray vanishes in the dark, so add a small light to the basket if you're walking outside.
40. Dorothy And Toto Costume
Bringing your own dog turns this into a duo, but the dog's comfort comes first. Wear the gingham pinafore and white puff-sleeve blouse with white ankle socks and secure red glitter flats or sneakers, plus braids with blue ribbon and rosy makeup with a red tint. Dress the dog in a light gingham bandana or soft vest that leaves the legs and chest free; most dogs put up with a bandana far better than anything with sleeves. Only carry a pet in the basket for photos if it's small and well supported, and use the basket for treats, bags and water the rest of the time. A red leash matches the shoes. Watch for panting or pulling at the vest, and take it off as soon as you see either.
Short Hair, Rain and a Basket You'll Carry for Hours
If your hair won't braid
Shoulder-length hair can usually manage two short braids if you start them high, just behind the ears, and a ribbon tied over the end hides a stubby tail. Shorter than that, I clip two ready-made braids in under the ribbon or use a braided wig. Cheap synthetic wigs tangle at the neck where they rub a collar, so comb them out gently with a wide-tooth comb before the night and keep them away from oven doors and candles; synthetic fiber frizzes or melts near heat.
Keeping the basket and Toto in one piece
A wicker basket is charming for the first hour and a nuisance by the third. I run a crossbody strap through the handle so it hangs at the hip, and I stitch or zip-tie the plush dog to the lining through its back so it doesn't tumble out when you bend down. Line the basket with a scrap of gingham and it doubles as a treat bag. Check the rim for loose wicker ends too, since they snag tights and tulle.
When the forecast turns wet
Cotton gingham shows water marks and glued glitter can soften in the rain, so on a wet night I'd wear the sneaker version and pack a clear poncho in the basket. A clear layer keeps the checks visible, where a dark raincoat turns you back into someone in a coat.
Blue Checks First, Then Make Her Yours
Every version here keeps a few details together: blue checks, a white layer, braided hair, red shoes and a basket or a dog. Hold on to most of those and you can follow the original closely, swap in sneakers, add decade pieces, dress for a cold night or mix Dorothy with another character from the story. Adjust the fit for age and size, choose fabrics you can breathe in, fix accessories so they stay put, and pick shoes you can actually walk in. If you're short on time, I'd start with the closet-built version and a pair of glitter shoe clips, then spend whatever time is left on neat braids.
Related posts:
