Ugly Shirt Draw

Ugly T-Shirt Challenge Rules

A secret name draw for group trips. Everyone buys one person the worst shirt they can find, and the whole crew wears theirs on the same night.

Run a draw for your group

What you need

  • A group of three or more.
  • A spending cap everyone agrees on.
  • One night when every shirt gets worn.
  • A way to draw names so nobody sees the whole list.

How to play

  1. Pick the night. Choose one dinner or night out when the shirts go on, and tell everyone before the trip.
  2. Set a cap. Somewhere from $10 to $20 works. A low cap keeps it about the hunt, not the money.
  3. Collect sizes. Ask ahead of time. A shirt that doesn't fit is an excuse not to wear it.
  4. Draw names in secret. Each person draws one other person, and nobody knows who drew them. The draw page does this and gives you a private link to send each person.
  5. Shop. Buy before you leave, or hunt once you arrive. Souvenir stalls, markets and thrift stores are where the worst shirts live.
  6. Hand over and wear. Give out the shirts just before the big night. Everyone puts theirs on and keeps it on until the night is over.

House rules

  • No hints about who you drew.
  • No swaps once the names are drawn.
  • You wear what you get, all night.
  • Stay under the cap.
  • Ugly, not cruel. Aim for loud and ridiculous, not for something a person couldn't wear in public.

Ways to make it worse

  • Style briefs. Deal each buyer a direction to shop toward, like “cruise-ship magician” or “too many flamingos”. The draw page can deal these for you.
  • Local only. Every shirt has to be bought at the destination.
  • Thrift only. Second-hand shops and nothing else.
  • Vote on it. The group picks the worst shirt of the night. The person who bought it takes the glory.
  • The photo. One group picture in the shirts, repeated every year.
  • Winter version. Swap shirts for ugly sweaters in December.

Common questions

How many people do we need?
Three or more. With two, there is no secret to keep.
What about couples?
Keep them apart in the draw so they don't buy for each other. The draw page has a setting for it.
What if someone joins late?
Redraw if nobody has shopped yet. If people have, let the group choose a shirt for the newcomer together.
Do we need a website to play?
No. Paper slips in a hat work when everyone is in one room. The draw page helps when the group is spread out, because nobody has to see the whole draw, not even the organizer.
Is the draw page free?
Yes. There is no sign-up, and the draw runs on your own phone.
Run a draw for your group