10 Best Costumes from our Pineapple Pup Costume Contest

October was such a fun month for us here at Staypineapple as we got to enjoy all the cute and hilarious dog (and sometimes human) costumes that were entered into our annual Pineapple Pup Costume Contest.

When judging costumes, we always appreciated something that was handmade, had accessories, and like us, was a little out of the ordinary. We were honored to give Bear and His Boy our grand prize of two complimentary nights at any of our hotels for his impressive 31 costumes in 31 days, some of which were shared via entertaining video.

For all the dogs out there who didn’t win but are still interested in treats and sleeping on a Staypineapple doggie bed, you can always save a few bucks at any Staypineapple hotel with the Pineapple Pup Package.

Without further ado, here are our favorite 10 entries from the contest!


Last year’s champ, 2husketeers brought the creativity again with multiple costumes that were lead by this furry pharoah. Maybe the hieroglyphics got it wrong and the ancient Egyptians actually worshipped dogs?


808london_hawaii was a strong participant in this year’s contest, putting together multiple out-of-the-box costumes. This vibrant choice made us think that he could surely survive in the world of Mad Max, at least in the fashion sense.


Who doesn’t like a bit of ice cream? Well Meeko the Pug had one of the cuter ice cream stands we’ve come across. We just won’t bother trying to solve how he scooped the ice cream with no opposable thumbs.


Heidi found herself in many custom costumes this October, all of which were documented by Amanda Conley Photography. We were partial to this gem that highlighted a nature-filled fishing expedition at a local watering hole.


This is either a great use of extras or the best photoshopping we saw all competition. One way or another, respect is due to Cosmo.


For all you Riverdale fans out there. Also impressive other than the costumes - getting Emie and company to pose perfectly.


Definitely the most EPIC shot of the month, Fox and the Gremlin perfectly captured the mythical lake creature.


Popular characters from animated movies are always a favorite. This year we had lots of Toy Story costumes, but this UP recreation from Hanna and the Tramp warmed our hearts the most.


Originality is always welcome, and Neville the Fluff Bottom nailed it with his Dwight Schrute from The Office. Next year, might we suggest our favorite, Toby?


A classic with a fluffy twist, Sukiyaki put it all together with this ode to Wizard of Oz. Also, we’re suckers for puns.

Those were our favorite 10! Thanks for reliving the memories with us, and we can’t wait to do it again next year!

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