50 First Dates is a lovely movie to dress from, because so much of it lives in clothes people already own: sundresses, Hawaiian shirts, cargo shorts and sandals. Lucy's bright dresses and Henry's relaxed shirts are the obvious picks, but the café, the aquarium and the boat give you plenty more, and so do the objects the story keeps returning to, like waffles, pineapples, newspapers and the morning tape. Because Henry spends the whole film finding new ways to meet Lucy again, it's a natural theme for couples and groups. Below are thirty ideas, from solo characters to pairs and a full cast, with notes on the pieces I'd thrift, the props that make the reference land and the shoes that get you through a party.
Thrifting Prints That Look Like Lucy and Henry
Nearly every costume in this list starts with a tropical print, and the wrong print is the quickest way to look like a generic luau guest. When I'm digging through a rack for this movie, I look for prints with a light, sunny background and medium-sized flowers. Very dark backgrounds and huge, loud florals read as a vacation shirt rather than as Henry.
What to check on the hanger
- Fabric: rayon drapes like the shirts in the film and feels cool, but it shrinks in a hot wash, so wash it cold or not at all before the night.
- Fit: men's shirts from that era were boxy with a straight hem worn untucked; a shirt that only works tucked in won't look right.
- Length on the sundresses: knee length or just above keeps Lucy sweet and casual, and lets you wear shorts underneath if you'll be sitting on the floor.
- Pairing: if you're dressing a couple, hold the two prints side by side in daylight. One small print beside one larger one looks planned; two busy prints of the same size fight each other.
1. Lucy Yellow Floral Café Costume
Lucy's breakfast look starts with a soft yellow sundress printed with small tropical flowers, knee length with short sleeves or wide straps. A light cream cardigan goes over it, and I'd take that seriously in October, since most of these dresses are thin rayon. Loose waves with one side pinned back by a yellow flower clip, rosy blush and a soft pink lip keep her fresh-faced. The props do the storytelling: a paperback, a folded newspaper and a plastic plate of waffles. A small woven shoulder bag holds your phone, and tan flat sandals or canvas sneakers carry you through the night.
2. Lucy Pink Hibiscus Dress Costume
A bright pink tropical dress gives Lucy's sunny side the most color. Look for a relaxed midi or knee-length cut printed with white hibiscus or bold leaves, and keep a cropped white cardigan in the bag if the evening turns cool. Medium-length blonde hair in loose curls works, or a natural wavy blonde wig. If you're buying a wig, pick one with some darker root showing; a flat, single-tone blonde looks like a costume wig from across the room. Tuck a pink flower behind one ear and keep the makeup peachy. A sketchbook and colored pencils point to her art, a pineapple purse makes the link to the movie, and wedge sandals or low white sneakers handle the walking.
3. Lucy Blue Tropical Sundress Costume
Blue gives Lucy's island wardrobe a cooler variation that still feels like Hawaii. Start with a blue sundress with white flowers, green leaves or a soft ocean print. Cotton and rayon both drape well, but rayon wrinkles badly in a bag, so hang it in a steamy bathroom before you leave. A shell necklace and a small woven bag are all the accessories it needs. Wear the hair loose with a white flower above one ear, and keep the makeup to tinted moisturizer, coral blush, mascara and pale pink lips. A newspaper with a handmade crossword pinned to the front gives you a prop. Tan sandals finish it, and a light denim jacket keeps you warm without hiding the print.
4. Lucy Art Teacher Costume
Lucy paints, so an art-teacher take on her is practical and easy. Tuck a light floral blouse into an ankle-length khaki skirt or loose linen pants, then put a paint-splattered apron over the top. Flick washable fabric paint off a stiff brush for the splatters; it looks far more convincing than paint dabbed on in neat dots. A low messy bun with a pencil through the hair tie, rosy cheeks and a coral lip suit her. Carry a sketchpad, a few brushes and a small cardboard canvas painted with a tropical scene. Flat sandals or canvas sneakers keep you comfortable, and a handmade Art Teacher badge helps guests who haven't seen the film in a while.
5. Lucy Memory Journal Costume
The memory journal is the emotional center of the movie, and it makes a quiet costume that people warm to. Wear a pale blue floral dress, or a white blouse with a flowing blue midi skirt, plus a soft cardigan and simple shell jewelry. Loose waves with a small blue flower clip, pink cheeks and a glossy lip keep the face soft. The journal is the real costume. I make it from a large scrapbook with today's date on the cover and fill the visible pages with printed photos, notes, hearts and drawings, glued down well so nothing flutters loose. Carry markers in a crossbody bag and let guests add a note, which makes it interactive. Tan flats or low sandals finish it.
6. Lucy Morning Video Costume
Lucy's morning video turns into a clever costume built from comfortable sleepwear. Wear a pastel pajama-style button-up over a white tank, with loose lounge pants or cotton shorts and a light floral robe on top. Soft, slightly tousled waves and almost no makeup suit the just-woken look. The props are a cardboard TV frame, a labeled tape and a remote. Hold the frame on a cord around your neck rather than carrying it, or your hands will be full all night. A date card stuck to the screen tells everyone what's going on. Slippers with real soles work indoors; white slip-on sneakers are safer outside.
7. Henry Green Hawaiian Shirt Costume
Henry is one of the easiest characters to thrift. An oversized light green Hawaiian shirt with white hibiscus goes over a plain white T-shirt, with loose khaki cargo shorts and a brown belt. When I hunt for that shirt, I go up a size or two, since the early-2000s fit was roomy and boxy, and a slim modern cut looks wrong. Keep the hair short and a bit messy, or use a dark brown wig, and add a little bronzer if you want an outdoor look. A toy fish, an aquarium badge or a small cooler works as the prop. A plain watch, a canvas bag and brown sandals or boat shoes suit his easygoing style.
8. Henry Aquarium Veterinarian Costume
Henry's job at the marine park gives you a work-uniform version of him. A blue polo or short-sleeve work shirt tucked loosely into khaki cargo shorts is the base, with a laminated badge, a utility belt and rubber gloves sticking out of one pocket. Short brown hair with some texture and natural skin finish him. Clip a plush penguin or sea animal to a clipboard of pretend care notes, and hang a toy stethoscope around the neck. Make your own patch for a blue cap rather than copying a real park's logo. Waterproof-style work shoes, white sneakers or brown walking sandals all fit.
9. Henry White Shirt First Date Costume
Henry's first-date look is the polished option. Wear a crisp white button-down with the sleeves rolled, dark straight-leg jeans and a brown belt. A neutral cap tames his tousled hair, or a short brown wig lifted a little at the front. Roll sleeves twice to just below the elbow and press the fold, otherwise the cuffs slide down every time you reach for a drink. Carry a shoulder bag with a dictionary and thesaurus, a nod to how he prepares before talking to Lucy in the café, plus a folded crossword. Brown casual shoes or clean sneakers finish it. On its own it looks like a nice outfit, which fans will enjoy decoding.
10. Henry Boat Captain Costume
Henry dreams of sailing, so a casual captain costume suits him. Wear a navy polo or striped T-shirt under a light tan utility vest, with beige cargo shorts and a weathered baseball cap. To age a new cap, rub the brim edge with fine sandpaper and give it a wash; a stiff, bright cap looks fresh off the shelf. Add a short brown wig if you need one and a little bronzer for sun. Carry a folded nautical map, toy binoculars and a cardboard boat wheel. A canvas duffel holds your things, and nonslip boat shoes or white canvas sneakers keep your footing. A handmade patch with a boat name makes the costume more specific.
11. Henry Roadside Date Plan Costume
Henry stages one elaborate meet-cute after another, and that gives you a funny roadside version. Wear a bright tropical button-down over a plain tee, cargo shorts and a cap, with windblown hair and a natural face. The sign is the joke. Cut it from light corrugated cardboard and letter it in thick marker with something like Need Help or First Meeting Today. Big, dark letters read across a room; thin pen disappears. Add a toy tool kit, a folded map and a clipboard listing conversation plans, plus paper date cards pinned to a messenger bag. Neutral sneakers or sturdy sandals fit the outdoorsy scene.
12. Henry And Lucy Café Couple Costume
This pair recreates Henry and Lucy's repeated café meetings, and both outfits are comfortable. Lucy wears a yellow floral sundress, a cream cardigan, blonde waves, soft pink makeup and tan sandals. Henry wears a green Hawaiian shirt over a white tee, khaki shorts, tousled brown hair and brown sneakers. Lucy carries a paperback and the crossword; Henry has a dictionary, a shoulder bag and a folded note of conversation starters. A plate of craft-foam waffles connects the two of them to that breakfast table. When styling a couple like this, I make sure the yellow and green prints don't clash in scale. A small floral beside a large leaf print is easier on the eye.
13. Henry And Lucy Pineapple Couple Costume
The pineapple is tied to Lucy's family's birthday routine, which makes it a sweet couple reference. Lucy wears a bright yellow floral dress, wavy blonde hair, rosy makeup and flat brown sandals, with a green leaf headband and a light craft pineapple. Henry wears a green Hawaiian shirt, khaki cargo shorts, sneakers and a simple cap, plus a small birthday calendar and a shopping bag of artificial leaves. Matching paper badges reading Pineapple Trip join them up. I'd avoid full foam fruit suits here, because they cover the clothes that make them Lucy and Henry. A craft pineapple is easy: a paper-mache ball painted yellow with a brown diamond pattern and a crown of green felt leaves.
14. Henry And Lucy Beach Couple Costume
A beach version suits a warm-weather party. Lucy wears a blue tropical sundress over modest shorts, loose blonde waves, coral makeup, a flower clip and flat sandals. Henry pairs a white T-shirt with an open floral shirt, beige cargo shorts, tousled hair and canvas sneakers. A woven beach bag holds a rolled towel, a sketchbook and a plastic sunscreen bottle; Henry can carry toy binoculars or an aquarium clipboard. A cardboard surfboard sign with a heart and a date photographs well. Keep swimwear covered. The thing that keeps this from turning into a generic luau is restraint: skip the grass skirts and leis and let the clothing stay everyday.
15. Henry And Lucy Wedding Couple Costume
The wedding version is romantic without needing formalwear. Lucy wears a simple white tea-length dress with short sleeves, a floral hair comb, loose blonde curls, rosy makeup and white flats. Henry pairs a light linen shirt with tan trousers, brown shoes and casual short hair. Linen creases the moment you sit, which actually suits a relaxed island ceremony, so don't fight it. Add tropical flower necklaces in coordinated colors and a small bouquet of artificial hibiscus. Henry can hold a handwritten vow booklet or a cardboard boat key, and Lucy's journal works as a second prop. Skip trains and stiff tailoring, especially at a crowded party.
16. Henry And Lucy Arctic Boat Couple Costume
The couple's cold-water sailing trip near the end of the film gives you the warmest option on this list. Lucy wears a blue sweater, dark jeans, snow boots and a cream puffer vest, with waves under a knit beanie and natural pink makeup. Henry wears a navy sweater, cargo pants, hiking boots, a weatherproof jacket and a brown knit cap. Paper luggage labels on light travel bags, a plush penguin, a folded sailing map and a cardboard ship wheel connect it to the voyage. Matching scarves tie the two together. For a trick-or-treat walk on a chilly night, this is the version I'd actually recommend.
17. Doug Blue Workout Costume
Doug, Lucy's gym-obsessed brother, makes a funny solo costume from comfortable athletic pieces. Wear an oversized blue mesh jersey with loose blue training pants or long athletic shorts, a wide brown lifting belt, black fingerless gloves, sport sunglasses and a red cap. Hair goes under the cap, and light bronzer is enough for the face. A small foam dumbbell is the safe prop, and a cord necklace adds a detail. Mesh jerseys are see-through and scratchy, so wear a plain tee in a matching color underneath. Black sandals or athletic sneakers depend on how far you'll walk. Leave the padded muscles at home; the attitude carries it.
18. Marlin Tropical Dad Costume
Marlin, Lucy's protective father, comes through as a relaxed island dad. Wear a muted tropical button-down in brown, green or navy with tan pants or knee-length shorts, a simple belt, reading glasses and a light cardigan. Style gray or salt-and-pepper hair neatly, with a natural-looking wig if needed. For a gray wig, I lightly dust the hairline with a matching powder so your own darker brows and temples don't contrast too sharply. Keep any age lines very soft. Carry a birthday calendar, an artificial pineapple and a family photo album, since those props tie him to his daily routine. Brown loafers or walking sandals, and a Lucy's Dad badge if you want help.
19. Sue Café Owner Costume
Sue, who runs the café, inspires a practical diner costume with island touches. Wear a colorful short-sleeve blouse under a solid apron, with black pants or a knee-length skirt. A handwritten name tag, an order pad and a few pens in the apron pocket do most of the work. Pick an apron with a deep front pocket; shallow ones drop pens every time you lean over. Tie dark hair into a tidy bun or ponytail and add a bright coral lip. Carry a light tray with foam waffles, a mug and a folded newspaper. Nonslip black sneakers suit restaurant work and a long party, and hibiscus earrings or a flower clip bring in the setting.
20. Alexa Aquarium Assistant Costume
Alexa, Henry's coworker at the aquarium, gives you a sharp, work-friendly option. Wear a teal polo or short-sleeve uniform shirt with navy cargo pants, plus a badge, utility belt, radio prop and a clipboard of pretend marine-animal schedules. Short, neat hair or a cropped wig and clean, understated makeup suit her. Carry a plush penguin, or stitch it to a canvas tote so it can't drop. Black work sneakers are comfortable for standing. To keep her distinct from Henry's veterinarian, lean on schedules and walkie-talkies rather than anything medical. A teal cap with a handmade wave patch finishes the uniform.
21. Dr. Keats Hospital Costume
Dr. Keats is a simple uniform costume with memory props to explain him. Wear blue scrubs under a white lab coat with a plain name badge and a toy stethoscope, plus supportive white or gray sneakers. Short, neat hair and a natural face suit the role. The clipboard does the explaining: an illustrated brain diagram, appointment notes and a calendar page. Thrifted lab coats are often sized generously, so check the sleeve length; if it covers your knuckles, a quick fold and a few hand stitches inside fix it. A stack of labeled memory cards and colored pens in the pocket add detail. Avoid real medical logos or anything that looks like working equipment.
22. Linda Travel Executive Costume
Linda's polished look is a smart contrast to all the island prints. Wear a fitted blazer over a satin-look blouse with straight-leg trousers or a knee-length pencil skirt, in a neutral like cream, navy or soft gray. A smooth shoulder-length blowout, defined lashes and a rose lip keep her groomed. Carry a structured handbag, a travel folder and a cardboard plane ticket, with a printed itinerary for an Alaska trip. Satin-look blouses show sweat marks quickly in a hot room, so pick a darker shade or a textured crepe if the party will be crowded. Pointed flats or low block heels, a slim watch and a name badge separate her from ordinary office clothes.
23. Nick Diner Cook Costume
A diner cook brings another café character into a group. Wear a plain white T-shirt under a short-sleeve cook's jacket, dark work pants and a striped waist apron, with hair covered by a paper diner hat or a clean bandanna. A tiny washable flour mark on one cheek is a fun touch. Carry a light spatula, an order ticket and a foam waffle fixed to a plastic plate. Glue the waffle down with a dot of hot glue on each corner, not one blob in the middle, or it spins on the plate. Black nonslip sneakers match the setting. Make your own café patch for the apron, and tuck a newspaper dated to Lucy's day into a pocket.
24. Stacy Café Server Costume
Stacy, the café server, wears a pastel blouse, a dark knee-length skirt and a contrasting waist apron. Add a name tag and tuck a few pencils into the apron pocket. A high ponytail or tidy bun with a tropical flower clip, coral blush and pink lipstick keep her cheerful. Carry a small tray with a plastic coffee cup, a foam waffle and a folded crossword. An order pad turns into a fun prop when you take pretend orders from other guests. Black ballet flats or nonslip sneakers are safe. In a group she fills out the café beside Sue, Nick, Lucy and Henry, and the pastel uniform keeps her from blending into Sue.
25. Willie Penguin Costume
Willie the penguin can be a cute animal costume without a bulky mascot suit. Black overalls over a white long-sleeve shirt create the black-and-white body. Add an orange bow tie, orange socks and soft orange shoe covers over black sneakers, then a black beanie with large felt eyes and a small orange felt beak. Stitch the eyes and beak onto the beanie rather than gluing, because knit stretches and glue cracks off as soon as it's pulled over a head. Rosy cheeks and a little white highlight around the eyes keep the face soft. Small black fabric wings attached at the sides leave hands free. It suits adults, teens and children alike, especially beside a Henry.
26. Jocko Walrus Costume
Jocko the walrus is a soft gray-and-tan outfit with a few felt details. Start with gray overalls or a gray sweatshirt with matching joggers, then add a tan felt belly panel and a hood or beanie with rounded ears. The tusks are the giveaway. I make them from white felt stuffed lightly with fiberfill so they stay soft and bend if someone bumps into you in a crowd. Gray makeup around the cheeks and nose, kept light and friendly, and gray sneakers or shoe covers carry the color down. A blue aquarium badge and a beach ball make the props. Pair him with Henry's uniform for a duo.
27. Waffle And Syrup Couple Costume
The repeated café breakfast inspires a food couple. The waffle wearer chooses tan overalls over a cream shirt with a light foam grid panel on the front, a yellow felt butter square on a tan beanie and brown sneakers. The syrup wearer dresses in a brown tracksuit with an amber felt label, a matching cap and brown shoes. For the grid, I score a sheet of thick craft foam with a blunt pencil instead of cutting it; the pressed lines look like waffle squares and the panel stays in one piece. Warm bronze makeup suits both, and plastic forks or menus beat oversized utensils. Tropical flower pins tie the food to the island café.
28. Pineapple And Birthday Dad Couple Costume
This duo pairs Lucy's family tradition with a pineapple. The pineapple wears a yellow shirt and matching pants with a brown felt diamond pattern, a green leaf headband, natural makeup and yellow sneakers. Laying the diamonds out with painter's tape before you glue keeps the pattern from wandering across the shirt. The birthday dad wears a muted Hawaiian shirt, khaki shorts, a gray wig, reading glasses and brown walking shoes, with a paper birthday crown, a calendar and a shopping bag. A small sign reading Picked Again Today explains the repeating day without a long story. Keep the fruit decorations flat and flexible, which makes this a good family-friendly option.
29. Memory Tape And Television Couple Costume
Lucy's daily video becomes an object couple. One person wears black pants and a black shirt under a light cardboard videotape frame, with a handwritten memory label, a black beanie and black sneakers. The other dresses in gray under a cardboard TV frame with rounded edges and an open center for the face and torso, plus paper buttons, a remote, a silver headband and gray sneakers. Tropical pictures, hearts and date cards around the screen make the reference clear. Use wide shoulder straps on both frames; thin cord cuts into the shoulders within an hour. I'd tape the inside edges of the cut-out with masking tape, too, since raw cardboard scrapes arms. It's strongest beside a Lucy or Henry.
30. Full Cast Group Costume
A full group lets the whole movie walk in together. Lucy wears a yellow floral sundress, blonde waves, soft makeup and tan sandals, and carries a book. Henry wears a green Hawaiian shirt, khaki shorts, tousled brown hair, an aquarium badge and sneakers. Doug takes a blue workout jersey, loose athletic pants, gloves and a foam dumbbell, and Marlin a muted tropical shirt with a pineapple calendar. Sue and Nick fill in the café with trays and waffles, and an aquarium assistant in teal can join, plus an optional penguin and walrus. Matching date cards on everyone link the group. With a big cast, I'd assign the shirts first, so two people don't turn up in the same green print.
Island Clothes on an October Night
The catch with this movie is that its whole wardrobe was made for warm weather, and Halloween usually isn't. A thin sundress or a short-sleeved shirt is fine at an indoor party, but on a porch or a walk it gets cold fast. I plan the warmth before anything else, so the extra layer looks like part of the character rather than a coat thrown over the top.
- For Lucy, a cardigan in cream or a color pulled from the dress print looks right for her, and skin-tone tights under a sundress are almost invisible from a few feet away.
- For Henry, a plain long-sleeve tee under the Hawaiian shirt keeps arms warm and still looks casual. Swap shorts for khaki trousers if it's really cold.
- Sandals are the hardest part. Canvas sneakers in tan or white keep the relaxed feel and save your toes.
Foam Waffles That Survive the Party
Waffles show up in half of these ideas, so it's worth making a batch that holds up. Cut squares from a thick sheet of tan craft foam, press a grid into each with a blunt pencil or a ruler edge, then dab on a little brown acrylic and wipe it back so it sits in the grooves. A drop of yellow paint for butter finishes them. Foam waffles weigh almost nothing, don't break if they hit the floor, and can be glued to a plate, a tray or an apron. Paper or real waffles look good in the first photo and fall apart soon after.
One Tropical Print and One Story Prop
One romantic comedy covers a lot of ground here: solo looks, couples, animals, food and a full cast. The easiest way in is everyday tropical clothing plus one strong story prop. Floral dresses, Hawaiian shirts, café aprons, aquarium badges, pineapples, waffles and the morning tape each tell people which movie you mean. Let hair, makeup and shoes support the character without making you uncomfortable. Copy a familiar outfit from the film or build a playful version around a place, an animal or a recurring object. Clear details and a couple of coordinated accessories are what get you recognized, and a warm layer is what keeps you at the party.
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