Dress up game ideas: 30 style challenges

These work three ways. You can play them in the photo dress up game (with only five pieces, the challenge becomes picking the best of six outfits for each person and defending your choice). You can play them in the outfit maker with your own clothes. Or you can play them for real, with a closet, a mirror and a friend who keeps score. None of them need anything you do not already have.

How to run a round

Draw a theme, set a limit if you like one (five minutes, three pieces, one color), dress up, then show each other. The fun part is the explaining: why the stripes say "seaside", why the jacket is the only sensible choice for a museum. If you want a winner, let the person who did not pick the theme decide. No points needed.

The thirty themes

Everyday days out

1. Picnic in the park. Light colors, nothing that minds grass stains less than you do. Reach for: pale trousers, a striped top, flat shoes. Harder: it is picnic day and the forecast says rain by noon.
2. Museum day. You will walk for hours and stand still a lot. Reach for: a layer you can carry, comfortable shoes, one interesting color. Harder: dress like a painting in the gallery.
3. Saturday farmers market. Early start, cool morning, warm noon. Reach for: a jacket over a tee, sturdy jeans. Harder: make the outfit match the fruit you plan to buy.
4. A quiet afternoon at the library. Cozy, soft, nothing that rustles. Reach for: a knit sweater, relaxed trousers. Harder: dress as your favorite book cover.
5. A day at the zoo. Lots of walking, sun and shade. Reach for: layers, sneakers, a color that makes you easy to find in a crowd. Harder: pick an animal and dress in its colors without looking like a costume.
6. Boardwalk in the off-season. Windy, bright and chilly. Reach for: stripes, a jacket, jeans. Harder: no blue allowed.

Weather rounds

7. The first warm day of spring. Everyone overdresses or underdresses. Reach for: one light layer, a pale color. Harder: the outfit has to work at 8 a.m. and at 3 p.m.
8. Cold, dry and sunny. Reach for: a thick knit, dark jeans, warm shoes. Harder: make winter look bright instead of dark.
9. A rainy Saturday indoors. Reach for: the softest things you own. Harder: still dressed enough to answer the door.
10. Heat wave. Reach for: loose shapes, light fabric, light colors. Harder: it is also a dressy occasion.
11. First leaves on the ground. Reach for: warm yellows, rust, a jacket. Harder: use autumn colors without any brown.

Color challenges

12. One color, head to toe. Different shades of one color only. Harder: use at least three textures so it does not look flat.
13. Primary colors. Red, blue and yellow, like a toy box. In the photo game, the cobalt jacket and the yellow sweater are both in play. Harder: make it look grown-up.
14. No color at all. White, gray, black, navy, denim, cream. Harder: make it look cheerful anyway.
15. Ice cream shop. Pastels only: mint, butter, pink, lilac. Harder: one dark piece allowed, and it must make the pastels look better.
16. Match a picture. Pick any photo (a sunset, a postcard, a cereal box) and dress in its colors. Harder: the other players have to guess which picture.
17. Stripes and something. One striped piece plus one other pattern. Harder: the two patterns must share a color.

Story rounds

18. The detective arrives. Dress the person who solves the mystery. Harder: now dress the suspect.
19. Launch day at mission control. Smart, practical, ready for a long shift. Harder: dress the astronaut on their day off.
20. Ferry captain. Stripes are almost too easy. Harder: no stripes.
21. The baker who opens at 5 a.m. Warm, practical, flour-friendly colors. Harder: the baker is going straight to a party after.
22. The painter's studio. Workwear and a jacket with pockets. In the photo game, the chore jacket was made for this one. Harder: make it look like an art opening.
23. Time traveler. Pick a decade and hint at it with one piece. Harder: pick two decades in one outfit.

Occasion rounds

24. Family photo day. Coordinated, not matching. Harder: dress three people who each choose their own top.
25. First day of school or work. Comfortable, a little bit special. Harder: you do not know the dress code.
26. A birthday lunch. Festive but sit-down. Harder: it is your grandmother's birthday and you want her to approve.
27. Packing for a weekend. Three days, one small bag. Every top must work with every bottom. Harder: one pair of shoes.
28. Outdoor concert. Standing, dancing, a chilly evening. Harder: dress in the band's colors without a band shirt.
29. Outfit swap. In the photo game, dress Rosa in the outfit you picked for Jun and see if it still works. Harder: find the one outfit that works best on all three.
30. Opposite day. Dress in the outfit you would never choose. Harder: make it look on purpose.

Tips for making it fun for everyone

Keep it about the clothes, not the bodies. A good rule at any age: comment on colors, shapes and how an outfit fits the theme, never on whether someone is too tall, too short or too anything. The three people in the photo game were chosen to look different from each other, and part of the fun is seeing that the same pieces can look good in different ways.

Let people pass. Not everyone likes every theme, and "I would wear this on a rainy Saturday" is a fine answer to almost any round.

Save the good ones. In the game, press Save and the outfit goes onto your shelf with its name. In the outfit maker, press Keep. Both stay in your browser, so nobody else can see them unless you share the link.