Irresistibly Charming: Unforgettable Moments from The Chronicle’s Homemade Halloween Costume Contest

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Over a decade ago, The Chronicle’s homemade Halloween costume contest began with the assumption that the costumes would be humorous, resulting in images that could be seen as “Pinterest fails.” The initial intent was to share a laugh, then move on.

However, the tone of the contest shifted when a creative email arrived featuring a girl dressed as a Converse Chuck Taylor sneaker. From that point forward, the contest evolved to showcase increasingly cool, creative, and epic costumes.

This year, the contest makes a triumphant return as the “Total SF Halloween Costume Contest.” The Chronicle is offering cash prizes, including $250 for the best San Francisco-themed costume. Submissions can be sent to with the subject line “Total SF Halloween.”

Here are ten of the most memorable costumes in the contest’s history:

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  1. Space Shuttle Endeavor and Jet Longtime reader Rhean submitted this topical costume in 2012, after the Space Shuttle Endeavor toured the Bay Area. The costumes featured Rhean’s daughter as the jet carrying the Space Shuttle Endeavor (her brother), creating a heartwarming and delightful image.

  1. Little Red Corvette Prince A young Prince admirer made a grand entrance with his Little Red Corvette costume in the 2014 contest. The costume showcased the boy’s love for the iconic musician and his hit song.

  1. Little RBG One of the winners from the 2012 contest featured a girl dressed as Ruth Bader Ginsburg. This poignant entry captured the girl channeling the spirit of the iconic justice, complete with RBG’s signature glasses.

 

This contest has evolved beyond its humble beginnings to become a showcase of creativity, heartwarming moments, and community engagement. The costumes that have graced its history represent a diverse range of themes, talents, and passions. As the contest continues, it promises to bring more delightful and imaginative moments to light. If you have a creative costume in mind, be sure to participate for a chance to add your own touch to this beloved tradition.

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