Category Archives: Ugly Sweaters
Uncle Ugly’s Christmas Sweater Jamboree 2010
*For complete viewing pleasure you will need to click on the photos to enlarge them. There were just too many and they were just too big. And now they are too small. And hard to see. Hence the need for the clicking.*
Last Christmas my husband, Cool Daddy, came up with the idea of having an Ugliest Christmas Sweater competition for the following year. It sounded just like the weird sort of thing our family would love, so I agreed and we made our plans.
On Christmas Eve Cool Daddy and I hosted The First Annual Uncle Ugly’s Christmas Sweater Jamboree. Everyone in the family participated except for the babies since we figured that a tricked-out sweater might be a choking hazard.
The Ugliest Christmas Sweater Champion would be awarded the Ugliest Christmas Sweater Trophy of Awesomeness. Contestants also had the opportunity to win the title of overall Most Festive Attire and Most Naturally Ugly (unaltered) Christmas Sweater (they’d win the title and bragging rights, but no award).
Here are all of the 2010 Ugliest Christmas Sweater Contestants…can you guess who won?
(The winner is announced at the bottom, so don’t scroll down and cheat! Cheater.)
First here we are, the Cool Family.
I think our sweaters prove just how cool we really are. Ahem.
When planning the party I didn’t consider the fact that Adaline might be freaked out by all of the sweaters.
I thought she would love them and try to pull at them.
Well.
Adaline was freaked out by all of the sweaters.

Isn’t that the ugliest Santa head?!
I found it at The Dollar Tree. What a treasure.
There were lights around the Santa head but they didn’t show up on camera ![]()
My hat had Santa legs coming out of the top (so that it looked like Santa was going down the chimney), but the legs kept flopping over, so it just looks like I’m wearing a brick-print top hat
.
Still awesome, but not quite the same. Sigh.

Cool Daddy can rock a woman’s sweater vest like nobody’s business.
There’s lights on the front and back (but again, they’re hard to see) and it’s covered in glow sticks. I’m not really sure why.
He’s wearing a Christmas tie that plays Jingle Bells (um, awesome, anyone?).
He purposely shaved off his goatee to have his creepy mustache compliment his sweater.
You better believe it was gone before the night was out. *Shutter*

So my sister waited until only a few days before to get her sweater together. Then decided that she couldn’t find anything (that she was willing to pay for), so she turned a shirt inside out and wrote all over it with a Sharpie. Um, okay.
She did even less for her husband having him wear an old sweatshirt, which for some reason he decided to fold up into a mid-drift. Sure.

I wised up when taking the picture of my mom’s sweater and turned off the flash so that you can see her lights. The lights on her sweater were s-weet! They were shaped like stars and changed colors!
(P.S. The tinsel on her sweater forms a Christmas tree…in case you couldn’t tell.)

Oh Christmas Ben, Oh Christmas Ben, how lovely are thy sweater…
My cousin Ben is sporting a Christmas tree sweater, complete with presents for shoes. A jingle bell fur collar adds musical appeal while tinsel and Christmas trees on the back make sure that you have a Happy Holiday from every direction. Oh yes.

On the first day of Christmas my true love gave to me,
a peacock in a pear tree…
Okay, so I think that my cousin, Aunia’s, sweater is actually kinda cute. And I would totally wear it to the grocery store peacocks on the shoulders and all.
(Then again I would wear my totally rockin’ Santa sweater to the grocery store too because I’m super weird and have no shame…)
She’s stylin’ with a pear tree on the front of her sweater, peacocks on her shoulders (because apparently partridges are hard to come by) and feathers on the sleeves.

My aunt, A.C., is trimmed in lovely green tinsel and featuring giant candy canes surrounded by puffy balls.
My uncle, U.A., is wearing a sweater that I originally thought was a reindeer head…and now I think might be a clock. Not really sure.
Either way, my favorite part was that he had real mini candy canes in the stockings. Tee-hee ![]()

Now’s your last chance to pick your winner
before scrolling down to see the results.

Okay. So here are the 2010 winners of Uncle Ugly’s Christmas Sweater Jamboree Ugliest Christmas Sweater Contest.
My brother-in-law, Matt, won the title and bragging rights for Most Naturally Ugly (unaltered) Christmas Sweater because he had the only unaltered shirt…even though it wasn’t Christmas-y. But my sister said that it has red and green on it so it counts. I guess.
Ben won the title and bragging rights for overall Most Festive Attire.
Wearing an entire Christmas tree on your chest will do that.
Have a Holly Jolly Christmas.
My very own main squeeze, Cool Daddy, rose victorious as the Ugliest Christmas Sweater Champion.
I think we all voted for him because we were so creeped out by the mustache.
And we wanted it to go away.
Very quickly.
And never return.

And this is supposed to be a picture of Ben sad because he didn’t win the trophy, but the sad picture that I took of him ended up being really blurry and so I used this one instead wherein he is kinda smiling and holding up one finger even though he was very sad and truly tortured to the very core of his being for not having won the trophy and he must be pretending that he is number one in order to make himself feel better and not cry in front the entire blogosphere. I thank you for not laughing at him during his hour of great pain and distress.
(Nothing says, “Feliz Navidad!” like a good nonsensical run-on sentence.
You are welcome.)

Hope you had a Merry Christmas! Keep it ugly
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Uncle Ugly’s Christmas Sweater Jamboree Rules
This year Cool Daddy and I are planning on starting a new Christmas tradition with our family. We usually go to my mom’s on Christmas Eve, but this year we are going to host the festivities at our house. And not just any festivities…Uncle Ugly’s Christmas Sweater Jamboree featuring the Ugliest Christmas Sweater Contest. We’re excited to see how this turns out and I thought that I’d share the Ugliest Christmas Sweater Contest Rules with you in case you were planning your own party this year. Enjoy.
Photos and results from the 2010 Ugliest Christmas Sweater Contest are here! Enjoy the Ugly
Uncle Ugly’s Christmas Sweater Jamboree
Featuring the Ugliest Christmas Sweater Contest
Contest Rules and FAQs
To be eligible as an Ugly Christmas Sweater Contestant you must wear a Christmas or Winter themed Sweater, Sweatshirt, or Sweater Vest to the Jamboree. Turtlenecks and long or short-sleeved t-shirts will not be accepted. You may wear such items underneath an Ugly Christmas Sweater-vest, but it will not be considered part of your sweater and therefore not eligible for judging. You may add to or alter your Christmas sweater however you like, have fun and get creative. Additional items such as hats, jewelry or other festive attire will not be considered when voting for the Ugliest Christmas Sweater. An item must be attached to your Christmas sweater in order to be eligible.
You can be disqualified from the Ugliest Christmas Sweater Contest for the following:
+Putting on your ugly Christmas Sweater after entering the jamboree (You must be already wearing your sweater when you show up to the jamboree.).
+Removing your sweater before the Ugliest Christmas Sweater Champion has been announced.
+Altering your Christmas sweater after entering the jamboree (Any and all alterations or additions to your sweater must be completed before entering the jamboree.).
+Swapping your sweater with another contestant before the Ugliest Christmas Sweater Champion has been announced.
+If you are overheard using the word “boring” anytime before the Ugliest Christmas Sweater Champion has been announced.
+If your sweater does not have a Christmas or Winter theme
+If your “sweater” is actually a t-shirt, turtleneck, or any shirt other than a sweater, sweatshirt, or sweater vest.
How will the Ugliest Christmas Sweater Champion be determined?
All eligible Ugliest Christmas Sweater Contestants will have the opportunity to vote for the champion. You may not vote for yourself. You must vote for someone. Anyone not competing and anyone who has been disqualified are not permitted to vote for the Ugliest Christmas Sweater Champion.
What will the Ugliest Christmas Sweater Champion receive?
The Champion will receive the coveted Ugliest Christmas Sweater Trophy of Awesomeness.
Will any other prizes be awarded?
Contestants will also have the opportunity to vote for the person with the overall Most Festive Attire and the person with the Most Naturally Ugly (unaltered) Christmas Sweater. The winners of these categories will win only the title and bragging rights. No prizes will be awarded.
Where do I get an Ugly Christmas Sweater?
I don’t know. That’s your problem. I’ve got my own sweater to find.
Uncle Ugly’s Christmas Sweater Jamboree is only two weeks away! Start looking for or making your Ugly Christmas Sweater right away!
Other Christmas Posts:
+Dear Santa: Part 1 Writing a Letter to Santa
+Dear Santa: Part 2 Mailing a Letter to Santa
+Dear Santa: Part 3 Paper for Writing a Letter to Santa
+Dear Santa: Part 4 Emailing a Letter to Santa
+My Letter to Santa 1984
+10 Ways to Shake Up Your Christmas Pajamas Tradition
+Phone Calls from Santa
+Uncle Ugly’s Christmas Sweater Jamboree 2010 Photos and Winners
+Traditions, Truces, and Cartoon Moments
+Food as Tradition: Norwegian Butter Cookies
Coolest Family on the Block is committed to helping you find creative ways to have fun and make memories with your family this holiday season. Don’t miss an idea, tip, or trick…subscribe and have updates sent directly to your email!
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