(from left: Erik, Lisa, Jenny, Alie the Intern, and scared Elyse)

This all began at the Zazzle HQ’s business park’s annual fiesta. Free sombreros were handed to each of us, we wore them and ate tacos – twas an enjoyable event. But now we are back at our desks, still wearing these festive caps, wondering when the party will end. So it was decided – the weakest willed shall determine el fin.

The challenge is simple: Last sombrero standing wins. Sombreros must be continuously worn during work hours. This includes meetings, lunches, and, most importantly, potty breaks. We are all very stubborn individuals so this could go on for days, weeks, etc. I am terrified.

What do you think should be my the winner’s prize? Share in the comments below!

Feel free to place bets and stay tuned!


  1. Reyu Says:

    That is so cool! I wish my work was as fun ;D There should be some kind of punishment for the first loser as well!!

  2. Caroline Everitt Says:

    I think that a cruise to Mexico would be a great prize. Thanks for sharing this with us all. What a silly and fun thing to do. Way to go Zazzle employees.

  3. Garrett Williams Says:

    Free taco!

  4. charlene Says:

    I don’t know what the prize should be but Erik is the only one with his hat tied to his head.

  5. SeItUp Says:

    Clearly, the winner should take possession of everyone else’s sombrero! ;)

  6. Arold Augustin Says:

    I think the winner prize should be a check.

  7. Hamilton Says:

    This takes serious determination, so the prize has to be awesome! If I was the winner I would want a personalized poster stateing that I was the Sombrero Grand Champion, framed and hung in my office. Second I would want a bottle of Patrone and 2 tickets for a cruise to anywere but Mexico so I could rest my tired neck that has held up the oversided sombrero.

  8. Pam Says:

    I predict that Erik will win (ladies have too much hair for this to be comfortable for long) and his prize should be a chihuahua!

  9. KG Says:

    I like Hamilton’s idea of a framed poster for the winner’s office. In addition the winner should receive a gift card to their favorite restaurant.

  10. Bunny Boiler Says:

    Z winner: Gets to pick their favorite “Day of the Dead” T-Shirt from Z Marketplace. Z Losers: should be forced to eat a meal at Chevy’s.

    Erik’s tied hat strings do exemplify his determination and commitment. I’ll put my $ on that pony!

    V/R, BB

  11. Jes, Zazzle Community Producer Says:

    I can make a tiny sombrero out of sculpey for the winner! :)

    I think as people drop out they should bring lunch (or at least cookies or something) for the group.

  12. Ken & Faith Gauthier Says:

    The winner should receive massive amounts of margaritas, he’ll have a headache and will need to relieve the pain LOL
    The losers will have to peel him limes for said margaritas.
    Oh heck just let them have one big party! :)

  13. Jenny, zTrend Commentator Says:

    @Ken&Faith, “he?!” Said, “he,” only has a 1/5 chance. But I love the margarita idea! And @Jess, my desk would look great with that trophy addition.

  14. Ken & Faith Gauthier Says:

    @Jenny ooops sorry to many margaritas for me….I meant who ever wins…not meaning any gender in particular. May the last person standing against the cold harsh wind….win!
    Somehow this reminds me of the stand off between the “Zax” in the Dr Suess books LOL

  15. SOMBRERO CHALLENGE: The Three Amigos « Zazzle Blog Says:

    [...] been two whole weeks. Lisa, Erik, and I are still in it to win it. Erik says he’ll wear it until he’s dead. Holy guacamole. No need for Halloween [...]

  16. ¡Sombreros Candidas! « Zazzle Blog Says:

    [...] 3/5 are still participating in the Sombrero Challenge. [...]

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