How to Run a Virtual Ugly Sweater Contest for Remote Teams

Your team is scattered across four time zones, half of them have cameras off by default, and the annual holiday party is now a calendar invite labeled “Festive Sync (Optional).” We can fix this. A virtual ugly sweater contest is the rare remote event that people join five minutes early for, because nothing unites a distributed workforce like watching the quiet developer from the Denver office reveal a knitted llama in a Santa hat. This is the complete playbook: platforms, voting mechanics, award categories, and the prize logistics that trip up every first-time organizer. Follow it and your contest will be the highlight of the company holiday calendar. Maximum festive chaos, delivered over Wi-Fi.

Quick disclosure: some links below are affiliate links, which means we may earn a small commission if you buy through them, at no extra cost to you. It keeps the tinsel budget funded.

Why a Virtual Ugly Sweater Contest Works When Other Remote Events Flop

Most virtual holiday events fail for one reason: they ask people to perform. Trivia demands knowledge, virtual escape rooms demand cooperation at 4pm on a Friday, and “share a holiday memory” demands vulnerability in front of the VP of Sales. An ugly sweater contest only asks people to wear something ridiculous and sit there. The sweater does all the work.

It also scales beautifully. Five people on a call? Contest. Four hundred people across three continents? Still a contest, just with async voting. And because everyone appears on camera anyway, participation is visible, which means the event builds its own hype as each person joins the call looking progressively more unhinged.

Step 1: Pick Your Platform

You almost certainly already have the tools. Here is how each one handles a contest.

Zoom or Google Meet (live contest)

Best for teams under about 50. Everyone joins with cameras on, contestants get a 15-second “runway moment” where they fill the spotlight view, and voting happens live. Zoom’s built-in polls handle the ballot; Meet users can drop a Google Form link in the chat. Pro tip from our Chief Festivity Officer: assign a host to pin each contestant during their runway walk, because nothing kills momentum like 30 seconds of “wait, who are we looking at?”

Microsoft Teams (live or hybrid)

Teams works the same way for live events, and its Forms integration makes ballots painless. If your company runs on Teams channels, you can also run the whole contest async in a dedicated channel, which brings us to the option most organizers overlook.

Slack (async contest)

For teams spread across time zones, async is the fairest format. Create a channel like #ugly-sweater-showdown, give people 48 hours to post a photo in their sweater, and let emoji reactions serve as votes. One emoji equals one vote, most reactions wins. It runs itself, nobody has to wake up at 3am for the Sydney office, and the channel becomes a highlight reel you can screenshot for the company newsletter.

Our recommendation

Under 50 people in compatible time zones: live on whatever video platform you already use. Over 50, or globally distributed: async photo submissions with a short live awards ceremony at the end. The hybrid gives you async fairness plus a live moment where winners get their applause.

Step 2: Set Voting Mechanics That Cannot Be Rigged by the Sales Team

Voting is where virtual contests go sideways. Choose one system, announce it before the contest, and enforce it.

• Emoji voting (Slack/Teams channels): one reaction per person per entry, votes close at a stated time. Simple and public.
• Anonymous form ballot: a Google Form or Microsoft Form with every contestant listed. Prevents popularity-contest awkwardness and lets people vote for the intern without office politics.
• Live poll: Zoom or Teams polls during the call. Fast and dramatic, but cap the field at about 12 contestants or the poll becomes a scroll of doom.
• Judging panel: three judges score each entry from 1 to 10 on ugliness, creativity, and commitment. Best for big contests where a popular vote would just crown the person with the most Slack friends.

Whichever you choose, publish the rules in the invite: who can vote, when voting closes, and how ties break. (Our house tiebreaker: the entrant who can explain their sweater’s backstory with the most conviction wins.) One person should own the tally. Give them a title. “Commissioner of Cringe” has served us well.

Step 3: Announce Categories That Give Everyone a Shot

A single “best sweater” prize means one winner and 40 people who stop caring by mid-call. Multiple categories keep the whole roster invested. Steal these:

• Ugliest Overall: the crown jewel. Blinding, baffling, unforgettable.
• Best DIY Disaster: for hot-glue heroes. Point contestants to our Top 10 DIY Ugly Sweater Ideas (With Step-by-Step Instructions) two weeks before the contest and watch the arms race begin.
• Most Festive Background: a remote-only category. Sweater plus decorated home office equals bonus chaos.
• Best Themed Duo: two colleagues coordinate across state lines. Melts hearts, wins newsletters.
• Best Pet Cameo: a dog in a tiny matching sweater beats every human entry. Accept this now.
• Most On-Brand: the sweater that best represents your company, product, or that one infamous outage.
• The “Technically a Sweater” Award: for rule-benders and loophole-finders. Every team has one.

Six or seven categories is the sweet spot for teams up to 100. Fewer feels stingy; more turns the awards ceremony into the Oscars, and nobody wants the Oscars.

Step 4: Run the Timeline

Two weeks out: send the invite with date, platform, categories, voting rules, and prize list. Include shopping links so nobody has an excuse. Our guides to the Best Men’s Ugly Christmas Sweaters and Women’s Ugly Christmas Sweaters cover every taste and budget, and the Cheap Ugly Sweaters roundup keeps entry costs under $30 for anyone watching their wallet.

One week out: post a reminder with one or two “inspiration” photos. If leadership participates, tease it. A CEO in a light-up reindeer knit doubles turnout, and we do not make the rules.

Contest day (live format): 30 to 45 minutes total. Five minutes of welcome, runway moments for each contestant, five minutes of voting, then awards. Keep it tight. A contest that ends while people are still laughing beats one that runs long.

Async format: 48-hour submission window, 24-hour voting window, then a 15-minute live ceremony or a results post with screenshots and fanfare.

One ground rule saves every HR follow-up email: state plainly that entries must be workplace-appropriate. The line exists, and some of your colleagues have browsed our Inappropriate Ugly Sweaters collection, so say it before someone tests it. If people ask what qualifies, send them to our office-safe ugly sweaters guide and let them go wild inside the fence.

Step 5: Solve Prize Logistics Before You Announce Prizes

Here is where remote contests differ from in-person ones. You cannot hand a trophy across a conference table, and shipping physical prizes to distributed employees involves collecting home addresses, which some people would rather not share with the party committee. Layer your prizes:

Instant digital prizes (zero shipping)

• E-gift cards: the workhorse. Coffee chains, food delivery, or a general card delivered by email within minutes of the win. Announce the winner and the prize lands before the call ends. Very satisfying.
• Winner certificates: printable award certificates make the win feel official and cost almost nothing. Zazzle has a full range of ugly sweater award certificates you can customize with your company name and each category, then email as a PDF or mail printed. Winners pin these to their home office walls for years. We have seen it.
• Bragging rights: a custom Slack emoji of the winning sweater, a “Reigning Champion” title in their profile, or a spot in the company newsletter. Free, and weirdly the most fought-over prize of all.

Shipped prizes (plan two weeks of lead time)

• A novelty desk trophy that shows up in the background of every future video call.
• A hot chocolate gift set for the cozy crowd.
• A ring light, the gift that says “your sweater deserved better lighting.”

Collect shipping addresses through a private form after winners are announced, never in the public channel. And run the printable ballots, scorecards, and category signs from the same planning kit you would use in person; our guide on How to Throw the Best Ugly Sweater Party Ever covers games, ballots, and party structure that translate straight to screen.

Level Up: Put the Whole Team in Matching Custom Sweaters

Want to turn a one-hour contest into a company-culture moment? Ship every team member a custom knit with your logo woven in before the event. The contest becomes “who styled the company sweater best,” the all-hands screenshot becomes recruiting gold, and the sweaters come back out every December like a uniform of chaos.

Our custom knit program handles exactly this for distributed teams, including bulk pricing and drop-shipping to individual home addresses so nobody on the party committee has to play warehouse manager. Get a quote through our corporate custom sweater page, or if you are an event planner running holiday programs for client companies, our event planner hub has volume options. One hard date to know: knitted orders need to be locked in by November 15 to arrive before mid-December contests. Printed all-over designs have a little more runway, but the knits are the ones people keep for a decade.

FAQ: Virtual Ugly Sweater Contest Questions

How long should a virtual ugly sweater contest last?

Keep the live event to 30 to 45 minutes: welcome, runway moments, voting, awards. For async contests, allow 48 hours for submissions and 24 hours for voting so every time zone gets a fair shot.

How do you judge an ugly sweater contest over Zoom?

Use a live poll for small groups, an anonymous form ballot for medium ones, or a three-judge panel scoring ugliness, creativity, and commitment for large contests. Announce the method and tiebreaker before the event starts.

What are good prizes for remote employees?

Lead with instant digital prizes like e-gift cards and customized award certificates, then add one or two shipped items such as a novelty trophy for the grand winner. Collect addresses privately after the results.

Can people who do not own an ugly sweater still participate?

Yes, and they often win. A DIY entry built from a plain sweatshirt, tinsel, and a hot glue gun competes in its own category, and budget-friendly options start under $25. No one gets to claim wardrobe poverty.

How do you get remote employees to participate?

Announce two weeks ahead, offer multiple categories so everyone has a lane, get one leader to commit publicly, and make voting anonymous. Turnout follows visibility, so tease entries as they arrive.

The Festive Folks’ Verdict

A virtual ugly sweater contest is the highest-return remote event you can run: one calendar invite, near-zero budget, and a screenshot that outlives the fiscal year. Pick the platform your team already lives in, run async voting if you span time zones, spread the glory across six or seven categories, and sort prize logistics before you promise anything that needs a shipping label. Do it right and this becomes the tradition your team asks about in October. Our Chief Festivity Officer rates a well-run remote contest a 10 out of 10 on the cringe-o-meter, and that is the highest honor we bestow. The uglier, the better. The louder the laughter over the speakers, the bigger the win.