Running Risks With That “Ugly Sweater” Contest

People at our office are always coming up with events to try to keep the workplace interesting.  Recently they announced that, on some date in the near future, there will be an “ugly sweater” contest.  With that innocent, well-intentioned decision, they placed the fashion-challenged among us at enormous risk.

The problem is that, once you get beyond a solid colored sweater, there is no sure way of distinguishing an “attractive” sweater from a repulsive one.  This isn’t an issue for men’s attire; few guys have a taste for sweaters as vivid and outlandish as those worn by Dr. Cliff Huxtable on The Cosby Show.  Women are another story, however.  You may see sweaters with hanging fuzzballs or swaying threads of yarn, scattered sequins, ribbons, or spangles, large Brutus Buckeye figures, bright orange pumpkins, or fake fall leaves sewn on, or blinding abstract designs that could have been ripped from the walls of the Guggenheim.  And there appears to be no rule of thumb that allows you to safely place one sweater versus another in the humorous, isn’t-this-a-razz,”ugly” category.

Therein lies the awful risk.  A guy might cheerfully tell a fellow passenger in the elevator that their sweater is a sure winner in the “ugly sweater” contest, only to realize from the icy response that the event isn’t until the day after tomorrow.  Or he might compliment a co-worker about her lovely ensemble, and then be advised that she thinks the sweater is hideous and certain to prevail in the competition.   The opportunities for a colossal faux pas are endless.

The safest course is to stay in your office, keep your head down in the common areas, and avoid any discussion until after the contest day has passed and a period of apparent sweater normalcy has returned.

103 thoughts on “Running Risks With That “Ugly Sweater” Contest

  1. The thing is that the ugly sweater became a trademark for Dr. Huxtable…so the more he was known for wearing them, the more he would wear them. Ridiculous looking or not.

    I guess I have a hard time distinguishing between ugly sweaters and “haute couture” sweaters…I would throw them all in the same category. 😉

    Cute post!

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  2. So true! I don’t know why you would have an ugly sweater day at work. I’ve been to ugly Christmas Sweater parties where everyone knows why they are there and what they are wearing. Good luck at work & Congratulations on Freshly Pressed!

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  3. I would be the one with the foot in my mouth! I made a comment to a recently divorced friend last week when we passed around birthday cards. I said, “for your new life.” It was a picture of a half naked studly guy someone else had brought. I immediately realized my mistake in that I should have said “with him she would officially be a cougar.” Several hours later she left a long message on my machine reaming me and telling me how thoughtless I was. If I had taken my time, I would have made the cougar remark instead,
    Oh for a few friends with a sense of humor……
    Congrats on being FP’d!!

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  4. The ugliest sweater has to be the one worn by the actor who played the stage producer in the movie, “Help” with the Beatles. It looked like the man was wearing a thick panda bear skin. And, he wore it all through the movie.

    One of the Beatles commented, “Look at that sweater. She must have knitted it for him.” Another Beatle replied, “It knitted him.” Connie
    http://7thandvine.wordpress.com/

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  5. We had this at my work. “Ugly Christmas Sweater Contest” and my boss wore a sweater she wears every Christmas season over and over. I did kind of feel bad since she actually thought this was a cute, (cotton ball covered) bell jingling, holly leaf sportin’ sweater. Good for her though for recognizing her “faux paux” and wearing it the day of the event. It got a lot of office buzz and she still wears it because she likes it. To each their own.

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  6. That sounds funny. We had nothing similar to that! Always kinda boring. I would find it even more interesting if people would exchange their sweaters at the end 😀

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  7. Women always have the advantage in an ugly sweater contest for two reasons: one, they can wear those seasonal sweaters with ghosts, or turkeys, or snowmen, or hearts on them; and two, men get knitted homemade sweaters that may very well be hideous, but that they would never wear for an ugly sweater contest out of respect for the woman who made it for them.

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  8. I once went to a party and a friend had to borrow his dad’s sweater – it was all he could find to wear. There was another man at the party – a family friend of the host’s – he was wearing a sweater, too. Both were wearing ugly sweaters at a non-ugly sweater party. My friend thought his was ugly. I can guarantee that was not what the family friend of the host was going for when he selected a sweater from his drawer.
    There is a picture to prove the awkwardness.

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  9. Funny and risque either way…. Fashion is a circle and it all depend on one’s liking, the sure way is to follow your style while staying aware of colors, patters and fit because if i had my way Neons would be agains the law, tie dye would be bye bye and ugly sweaders would be gag gifts but the sun rises and sets for every one even when our fashion compass seam to be in the burmuda triangle 😉

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  10. As a woman who’s made extensive study of knitting, I think I can help here:

    Arguile – Stylish
    Large, square plaid – ugly
    Cable knits – Stylish
    Shoulder pads – ugly
    Mild ruffle – stylish
    Gold and black – ugly
    Pastel and black – stylish
    Pilled – ugly
    Fine fuzz – stylish
    50% or more beads or sequins missing – ugly
    100% to 75% of beads or sequins still attatched – Stylish

    Gold and black with shoulder pads and a turtle neck – folks, we have a winner.
    Anything someone’s mom or grandma made – ignore all the rules, it’s beautiful!

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    • I love this! And I love that every guy is going to have to print this out and look carefully down the list before commenting! Too funny!
      I would have to say that since it’s not the 80’s anymore, you’re safer with thinking any amount of beads or sequins are just ugly. May I also add, it is difficult to determine the stylishness of sweaters with large holes, since to the untrained (non-knitter’s) eye, they may just look like unintended holes, when they are, in fact, stylish holes, purposely put there.
      I disagree with your pastel and black analysis. Kind of depends on the pattern it takes!

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  11. Contests like this were the birth of the innocuous comment that replaced compliments. IE: “that’s quite a sweater” replaces “nice sweater”.

    Bill Cosby’s got quite the sweater on in that picture.

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  12. This happened to my daughter. A group of young singles in our area was having an ugly sweater contest. When they called everyone up on stage that was competing, my daughter turned to the guy setting next to her and asked if he was going to go up. As he sat there looking at her, she realized that he was not part of the competition. Pretty much scarred the poor child for life. I am not sure she will recover.

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  13. I would love for us to have an Ugly Sweater Contest at my Church around the holidays. But I’m guessing someone’s feelings might get hurt. Just like beauty, ugly is also in the eyes of the beholder. Lol

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  14. I have a sweater that made everyone laugh when I would wear it to work. It got to the point that I would wear it just to get a response which mostly were, “Look he’s wearing that Cosby sweater again!” I admit, I just couldn’t get enough of it. Thanks for the blog!

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  15. Yes, an ugly sweater contest sounds like fun, but also a great opportunity for faux pas. I think I’d stick with only commenting on sweaters I truly like, and then if the wearer says they think it’s a good one for the ugly contest, I’d just giggle and say “Oh, well, I’d wear it, but that may not mean much! Haha” I love hand-knitting though. I know how much work a homemade sweater would take, so if any of them were handmade, I’d cheer no matter how they looked.

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  16. I think of the ugly sweater contests whenever someone puts a “favorite” heart on a Polo Ralph Lauren sweater I have in my vintage etsy shop, MistressOfMerlin. I know it is a valuable sweater, but… two guys paddling a canoe in a mountain scene??? I think it would look great on the right man, but I also wonder if people are looking at it as an ugly sweater candidate!

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    • Sorry, I’ve been on the road. Lots of the comments seem to urge avoidance — that, is, don’t show up on the day of decision — but others offer tips on how I can avoid that faux pas that inevitably is going to happy. I’m flattered with the latter comments, because they confidently presume that I am capable of distinguishing the stylish from the dreadful. I’m afraid that presumption is utterly misplaced — but I appreciate the vote of confidence!

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  17. I hadn’t thought about it like that, but you’re right. The “ugly sweater” thing is just a way to really stick your foot in your mouth. It reminds me of a little tip everyone should know…never ask a woman if she’s pregnant. Just like the ugly sweater that might not be ugly at all, that woman may have just recently had one too many donuts and not be baby bumping.

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  18. I should think most males in the office wouldn’t care a bit about whether or not a woman’s sweater is ugly. isn’t it what’s underneath that he’s more interested in?

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  19. I love ugly sweaters -blush-

    they are my secret, guilty pleasure

    I would definitely wear something hideous, it’s better than being normal haha

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  20. Ahhhh! too funny! Since we are required to wear a uniform ugly anything can not be competed for….but my goodness, I can see an issue in many a workplace!!!!

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  21. Somewhere recently I saw a photo of George Harrison wearing an extremely ugly sweater. I’ll bet I thought it was beautiful way back then, though! Actually, a lot of stuff I wore as a teenager, my mother would say, “Some day, you’ll look back at these clothes and laugh!” Dang, Mom was right again.

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  22. I have the same problem with T-shirts in my arena. I’m an aviculture writer and must attend bird expos, parrot festivals and aviculture conventions and some of the plug-ugliest t-shirts with birds on them are found on people wandering around at these events. Some of them are absolutely hideous but you can’t say anything.

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  23. LOVED THIS!

    I ran into a similar problem when I hosted an ’80s party. My 50-something friend with the hair that spikes STRAIGHT UP (think Pat Benatar circa 1982) told me she wanted to attend “without costume.” YIKES! I spent the entire night diverting disaster by adding into every introduction that she was a party-pooper and DIDN’T WEAR A COSTUME.

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  24. Someone should just get a sweater that has a knit depictions of various human rights abuses. That’d win for sure.

    Again, I suppose there is an off chance that could be someone’s favorite sweater that their mom made for them- but it seems less likely.

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  25. Don’t stay in your office and put your head down, instead put on your absolute favourite sweater, ugly or not, and march around with your head held high!!! Take any comments that come your way with pride, and tell everyone else you see in their sweaters, ‘that is a fantastic sweater’.
    Because you know what? We all don’t make the treks to Vallue Village to buy a god-awful hideous sweater, most of us have these hanging right in our closets? And why do we have them? Because we secretly like to curl up in the house when we’re all alone and wear these hideous things. Why do we do that? Because, well, we love them.
    Bring on Ugly Sweater Day!!!

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  26. I pride myself on my Ugly Sweater collection. It’s hideous, comfortable, warm, roomy and eclectic. I will never be cold, and I will never be boring. It is true that women have more room…I own no puff-ball wonders, though!
    Great post, thanks!

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  27. I love it when they have ugly sweater days at high school…but you do have to be careful about what sweaters you call ugly because some people really like them. I really admire the people that can put on a sweater that is butt ugly and make it look cute.

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  28. Bill Cosby’s sweaters are the equivalent to mom jeans. So awful. This reminds me of how people throw “holiday sweater” parties. The last thing anyone should have on a sweater is a reindeer with protruding antlers and a bell that really jingles.

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  29. Hah! Bill Cosby’s sweaters are not ugly. The color palette is appealing and there’s nothing furry or hanging out. It’s only around Christmastime or Halloween that the true ugly sweaters show its face. *shudders*

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  31. OH so true! I would suggest making the contest a little more specific so there’s no mistake like an “ugly Christmas” sweater contest. Or “ugly 80s” sweater contest. Or you could just avoid wearing sweaters all together until the dreaded day!

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