Ugly Sweater Trophies

The office holiday party trophy, with the categories and the rules to go with it

Short answer

An ugly sweater trophy is the prize for the worst, loudest or most ambitious holiday sweater at a party, and it works best as a perpetual: one trophy that returns every December with a new name on it. We design it from scratch in layered, full-color acrylic, so it can be shaped like a sweater, carry the company logo and be as tasteless as the occasion demands. Add two or three smaller awards for other categories. There is no minimum order, and you approve a design proof before anything is produced.

Layered acrylic award with a clear mountain-profile backing plate and a red and black cut-out X

One trophy, handed over every December

The best version of this contest has a single trophy with a history. It sits on the winner’s desk for a year, it is surrendered at the next party, and by the fourth year people are planning their sweater in October to win it back.

That is a perpetual award, and it needs two decisions at the start: how many years of names it should hold, and what happens when it is full. Both are easier to settle before the first winner than after.

Perpetual trophies covers plate counts and return rules. The trophy itself is a custom award, designed around your company and your sense of humor.

What to order

Custom acrylic award icon

The perpetual

The main trophy, cut to a sweater shape or built around your logo, with room for a name plate each year.

Layered award icon

A keeper for the winner

A small award the winner takes home for good, since the big one has to come back.

Pin and commemorative award icon

Category awards

Two or three smaller pieces for the other categories, so more than one person gets called up.

Categories that give more people a chance

A single “ugliest sweater” prize goes to whoever spent the most. A few categories spread it around.

Ugly sweater contest categories
CategoryGoes to
Ugliest OverallThe grand prize. The perpetual.
Best HomemadeGlue, felt and effort over store-bought
Most LightsAnything battery-powered
Best Team or PairCoordinated sweaters across a desk group
Most Likely to ShedTinsel, pom-poms and anything that leaves a trail
Vintage FindA sweater that was once worn sincerely
Best Remote EntryFor the team on the video call

Three or four of these are plenty. Pick them before the party and put them in the invitation.

Keeping it kind

The contest judges sweaters, not people. That sounds obvious, and it is where these contests go wrong.

  • Judge only what people chose to enter. Nobody gets a prize for clothes they did not mean as a costume.
  • Make entering optional, and make that clear. Not everyone celebrates the holiday or wants to dress up.
  • Keep the category names about the sweater.
  • Let the room vote, or use two or three judges. One judge makes it personal.

Funny award ideas and work superlatives both hold to the same rule: an award should be something the winner is happy to show their family.

More than one office, or half the team at home

A sweater contest is one of the few party traditions that survives a video call, because the entry is visible from the waist up. Two adjustments make it work across locations.

  • Vote from photos. Everyone submits a picture by a set time, and the vote happens in a shared channel. That puts the remote entry and the in-person entry on equal terms.
  • Decide where the perpetual lives. If the winner is in another city, the trophy has to travel. Either send it on, or keep the perpetual at one office and give the winner the keeper award.
  • One contest, not one per office. A single trophy that every site competes for is more fun than four small ones.

We ship nationwide, including to a winner’s home address. Awards for remote and hybrid teams covers what changes when an award arrives in a box.

What goes on it

The Golden Reindeer
Ugliest Sweater
Awarded Annually

Give the trophy a name of its own. A named trophy becomes a tradition, and “Ugliest Sweater 2026” does not. The year and the winner’s name go on the plate, not the trophy, so the piece itself never dates.

If the party also has serious awards, such as an employee of the year, keep them visually separate from the joke awards. Employee of the year awards and the award ceremony script cover that side of the evening.

What to send us

  • The name of the trophy and the company logo, if you want it on there.
  • How many years of name plates the perpetual should hold.
  • The other categories, if you want matching smaller awards.
  • The date of the party.

We send a design proof and you approve it before anything is produced. Request a quote with the party date and we will answer against it. More office event ideas are in the Recognition Library.

Ugly Sweater Trophies FAQs

What is an ugly sweater trophy?

The prize for the best, or worst, holiday sweater at a party. In an office it is usually a perpetual trophy that returns each December with a new winner’s name.

Can the trophy be shaped like a sweater?

Yes. Our acrylic is cut to shape and printed in full color, so the trophy can be a sweater, a reindeer or anything else you send as artwork.

How many years of winners should it hold?

Plan for at least ten. An annual party fills a small trophy faster than people expect.

Does the winner keep it?

Usually for a year, then it comes back for the next party. A small keeper award lets the winner hold on to something permanently.

What categories work besides ugliest overall?

Best homemade, most lights, best team or pair, and a category for remote staff. Three or four is enough.

Can you make just one?

Yes. A single trophy is all most offices need.

Racer in a helmet raising both arms as gold confetti falls under stage lights
PARTY ON THE CALENDAR?

Tell us what the trophy is called

Send the trophy’s name, your logo and how many years of winners it should hold. We design it and send a proof before anything is made.

Give us the party date and we will quote against it.

Request a Quote