Posted by: Barbara Evanhoe | June 21, 2011

Ugliest Hawaiian Shirt Contest

It was a fine Father’s Day afternoon in Cedar Key…sunny and hot…but it was cool inside the comfy digs at the Black Dog Bar and Tables, as folks came in for a cold one, glass of wine or fine cigar, along with a good dose of “Oldies”, performed by none other than “Me and My Baby”, while waiting for the 2nd Annual Ugliest Hawaiian Shirt contest to begin!

Sporting our finest in front of the "marquis" before the contest and show

Each time the door opened and a new Hawaiian shirt walked in, those already gathered would assess the competition, and shout out a sportsmanlike greeting, and/or challenge.

It was interesting to see what different people considered “ugly”…the “Key Lime Cowboy”, for instance had chosen a tan and pink Hawaiian print shirt and lime green straw cowboy hat, recently purchased at the consignment shop just a few blocks away.

Judges for the competition were the crowd at the Black Dog, and the vote was determined by the level of applause for each contestant. And, although The Key Lime Cowboy’s hat was pretty ugly, his shirt was just too cool, and it did not earn him a place in the finals.

The Key Lime Cowboy "poses" during "Secret Agent Man"

The Cowboy’s friend, who went by the name of “Wasabi” for the contest, had managed to find a Hawaiian shirt with an all-over sushi theme print. Unfortunately, the shirt was just too tame, and Wasabi was culled from the competition as well.

Keith was convinced that his newly purchased blue shirt adorned with large pink and purple fish would be a sure winner, but although he made it into the finals, he was knocked out by a little dog named Okeechobee, who was wearing a tiny white and tan flowered Hawaiian shirt.

Keith and his "nemesis", Okeechobee

I tried to enter the contest myself, with an orange sundress covered in red, green and white Hawaiian flowers, but I didn’t even get one vote ~ they said the dress was just “too cute” ~ so I will just have to keep my eyes peeled for an ugly MuuMuu, for the 2012 competition.

There were a number of other contestants who met the same fate…it appears that not all wild and crazy Hawaiian print shirts fall into the “ugly” category, but after this year’s competition, us “losers” have learned a bit, and could be serious contenders in the future.

The final contestant stepped up to be judged, sporting a worn blue Hawaiian print shirt, necklace made of “things that probably came off the beach”, and an old tie-dyed undershirt to set off “the look”.

Perhaps it was the “ensemble” effect, or perhaps it was the fact that this contestant arrived with an entire cheering section in tow, but she was proclaimed the winner, hands down, and presented with a $50 bar tab gift certificate.

Black Dog owners with the 2011 Champ, and one of her cheering section

After the contest, Keith and I hung out at the Black Dog for a couple of hours, relaxing and imbibing, and enjoying the company of friends, old and new.

Here I am, after the contest and show, relaxing with a fine glass of organic Merlot!

Keith was also treated to a Perdomo Habano cigar from the Black Dog humidor. He reports that it was a fine, enjoyable smoke, and could easily become part of his regular “stogie repertoire”. (Special note to brothers-in-law from Keith…give this fatty a try…ring gauge 52, about 1.5 hours smoking time!)

It was a good day!……..and oh yes, for those of you who celebrate the turning of the Wheel of the Year…..Happy Solstice!



  1. What a great article, Barbara!

    Jay & I have read it a few times and laughed and laughed. You really nailed to mood of the day! Imagine, an innocent victim of her own poor fashion sensibilities winning!! Perhaps next year will be the year for you – although being “too cute” really ain’t such a bad thing!!

    • Glad you enjoyed my “event report”…it was such fun!

  2. Ms. Babs — if you need a muumuu for the 2012 contest, I’ve got a dress for you. It’s polyester — not so comfortable in the Florida heat — but I guarantee, it’s ugly. Could be a winner! XO.

    • Thanks, Ms Becca – I will gladly take you up on the offer…I am sure that the muumuu is “divine”!

  3. Love that outfit BE – especially the hat!

    • Oh yes, we can be mighty fine if we put our mind to it 🙂

  4. We have some vintage clothing in our store that would be appropriate too. We actually sold 12 dresses to a vintage clothing store in Lawrence last week. 🙂

    • Was it Wild Man Vintage? I just love that shop! I’ll have to check out the vintage clothing section of your antique store when we are there in September.

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