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Oof that hits a sore spot. I was the 2016 Winner of the Ugliest Shirts Award at one of the first technology companies I worked at. Being singled out in front of all your peers for poor fashion sense and then the ensuing obligatory laugh ruined my opinion of that company's leadership. I would strongly encourage anyone in a professional environment (especially those in leadership roles) to keep comments on appearance to yourself.

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I'm sorry to remind you of a bad time. I would like to point out that "2016 Ugliest Shirts" is a pretty different concept from "Person who wore the ugliest shirt this week" with a picture of you in a ratty beloved tee. It sounds like those were year end remarks, which means instead of judging an act they were judging your long term taste. Also it implies the most memorable thing about you was your shirt choice. And lastly, you weren't anticipating it, so you found out everyone was secretly judging you on something.

If, during orientation you were told a trophy gets given out every week for it, and some people wear really ugly shirts each Friday to try to win it, it would have felt very different.

But yeah, year end humorous awards like that probably belong confined to episodes of The Office.

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