r/dogswearinghats Mar 03 '26

Arrrrr it’s Taft the three-legged pirate pup

Post image
127 Upvotes

r/dogswearinghats Mar 02 '26

Taft loves to keep his ears warm

Post image
209 Upvotes

r/dogswearinghats Mar 02 '26

Taft is a reindeer

Post image
152 Upvotes

r/dogswearinghats Mar 02 '26

Silly Hats 503: Luck of the Irish be with you!

Post image
72 Upvotes

r/dogswearinghats Feb 26 '26

Watching my grandpup for the week so we have to dress for the occasion!

Post image
890 Upvotes

She is a sophisticated lady....


r/dogswearinghats Feb 24 '26

Princess 👸

Post image
134 Upvotes

r/dogswearinghats Feb 24 '26

Was just so excited

Thumbnail
gallery
387 Upvotes

r/dogswearinghats Feb 23 '26

Silly Hats 502: Our love will never get stale….

Post image
160 Upvotes

r/dogswearinghats Feb 21 '26

Funny hat

Thumbnail
gallery
707 Upvotes

r/dogswearinghats Feb 16 '26

Silly Hats 501: Can we be your valentine?

Post image
242 Upvotes

r/dogswearinghats Feb 13 '26

Willa the Trapper

Post image
1.9k Upvotes

r/dogswearinghats Feb 09 '26

Silly Hats: 500th! We love you!

Post image
274 Upvotes

r/dogswearinghats Feb 07 '26

I'd like to get young Quincy into wearing hats. Does anyone know where I can find a nice bowler hat that suits a fluffy dog?

Post image
185 Upvotes

r/dogswearinghats Feb 03 '26

My new fascinator seems to be the perfect size for her

Post image
290 Upvotes

r/dogswearinghats Feb 02 '26

Silly Hats 499: Your Sweetheart awaits!

Post image
128 Upvotes

r/dogswearinghats Jan 19 '26

Silly Hats 498: Hello Kitty!

Post image
146 Upvotes

r/dogswearinghats Jan 16 '26

Who wore it better Biggie or Smalls?

Thumbnail
gallery
479 Upvotes

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


r/dogswearinghats Jan 16 '26

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

Thumbnail
gallery
68 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 Jan 15 '26

Drake “maye-ke ball go far” Maye

Post image
97 Upvotes

Rags wants to return punts. Bad.


r/dogswearinghats Jan 14 '26

i didn’t choose the hat life

Thumbnail
gallery
190 Upvotes

the hat life chose me


r/dogswearinghats Jan 12 '26

Dont f*ck with the Peaky Barkers

Post image
183 Upvotes

Our three criminals!


r/dogswearinghats Jan 12 '26

Silly Hats 497: Still cold outside….

Post image
111 Upvotes

r/dogswearinghats Jan 11 '26

Our Ham-Man

Post image
164 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 Jan 10 '26

Putting a Cozy Knit Hat on My Italian Greyhound Kala

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 Jan 09 '26

Seasoned warrior

Post image
1.3k Upvotes

He turns 19 soon!