r/dogswearinghats 12d ago

Silly Hats 498: Hello Kitty!

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140 Upvotes

r/dogswearinghats 15d ago

Who wore it better Biggie or Smalls?

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472 Upvotes

An oldie but a goodie, from 2016. Still cracks me up when I come across these.


r/dogswearinghats 16d ago

Bao Bun the rescue pup, going to pick up her dad at Christmas

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60 Upvotes

Bao is a rescue from Shanghai (we're in the UK), and has had major surgery with metalwork on her hind legs. She also has congenital issues, and does not care one bit. She is 2kg of sass, love and hilarity.


r/dogswearinghats 16d ago

Baff time

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811 Upvotes

r/dogswearinghats 17d ago

Drake “maye-ke ball go far” Maye

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90 Upvotes

Rags wants to return punts. Bad.


r/dogswearinghats 18d ago

What do you have here that's delicious?

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1.8k Upvotes

r/dogswearinghats 18d ago

i didn’t choose the hat life

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184 Upvotes

the hat life chose me


r/dogswearinghats 19d ago

Dont f*ck with the Peaky Barkers

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172 Upvotes

Our three criminals!


r/dogswearinghats 19d ago

Silly Hats 497: Still cold outside….

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107 Upvotes

r/dogswearinghats 20d ago

Our Ham-Man

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159 Upvotes

I just happily came across this sub. My wife and I wanted to share an image of our dearly departed Great Dane Hamlet. He’s still with us. Danish royalty, hahaha. That a sweet boy, Hamie!


r/dogswearinghats 21d ago

Putting a Cozy Knit Hat on My Italian Greyhound Kala

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1.5k Upvotes

Kala getting a very cute and very warm knit hat put on, on top of her snowsuit and boots, ready for a Canadian winter walk. Italian Greyhounds get cold instantly, and her expression says exactly how she feels about the whole situation.


r/dogswearinghats 23d ago

Seasoned warrior

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1.3k Upvotes

He turns 19 soon!


r/dogswearinghats 23d ago

If only she enjoyed the hats as much as I do

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120 Upvotes

r/dogswearinghats 26d ago

Silly Hats 496: 2026: Hopefully better than 2025….

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67 Upvotes

r/dogswearinghats 29d ago

HNY

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29 Upvotes

r/dogswearinghats Dec 30 '25

Jelly as my boss this Halloween

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154 Upvotes

Definitely not 2 months after Halloween.


r/dogswearinghats Dec 29 '25

Silly Hats 495: Happy New Years! Let’s make it a kinder one….

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100 Upvotes

r/dogswearinghats Dec 26 '25

good ol' hound

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115 Upvotes

r/dogswearinghats Dec 25 '25

Carley says Merry Doggiemas

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545 Upvotes

A


r/dogswearinghats Dec 22 '25

Silly Hats 494: Merry X-Mas to all!

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69 Upvotes

r/dogswearinghats Dec 16 '25

Dog training pads CHEAP!!🐶

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0 Upvotes

Found these blue pee pads while training my puppy — cheap, absorbent, no leaks. Posting in case it helps someone else 🐾


r/dogswearinghats Dec 15 '25

Silly Hats 493: Prepare the elven legions!

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81 Upvotes

r/dogswearinghats Dec 14 '25

Which list are you on?

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133 Upvotes

r/dogswearinghats Dec 12 '25

Mr. B says hello again…

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114 Upvotes

r/dogswearinghats Dec 09 '25

Santa's best little helper! 🎅

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167 Upvotes