For June and Beyond. Shop the Pride Collection.

Smug Man Caps

52 items

52 items

Item preview, I'm very clever man designed and sold by PenandFox.

I'm very clever man Dad Hat

Item preview, Rest assured, I'm incredibly wealthy... designed and sold by PenandFox.

Rest assured, I'm incredibly wealthy... Dad Hat

Item preview, Very much above average - man designed and sold by PenandFox.

Very much above average - man Baseball Cap

Item preview, Once again, I've landed on my feet man - ironic designed and sold by PenandFox.

Once again, I've landed on my feet man - ironic Dad Hat

Item preview, Stick with me, you'll go far - man designed and sold by PenandFox.

Stick with me, you'll go far - man Baseball Cap

Item preview, Definitely not a fashion victim designed and sold by PenandFox.

Definitely not a fashion victim Baseball Cap

Item preview, He who is not satisfied with a little... designed and sold by PenandFox.

He who is not satisfied with a little... Baseball Cap

Item preview, A stitch in time is worth two in the bush... designed and sold by PenandFox.

A stitch in time is worth two in the bush... Dad Hat

Item preview, Never yoga on a full stomach... designed and sold by PenandFox.

Never yoga on a full stomach... Dad Hat

Item preview, Definitely not a smoker designed and sold by PenandFox.

Definitely not a smoker Dad Hat

Item preview, Oh dear, I'm right again man designed and sold by PenandFox.

Oh dear, I'm right again man Baseball Cap

Item preview, Definitively not mad designed and sold by PenandFox.

Definitively not mad Dad Hat

Item preview, Be like water, but a bit drier... designed and sold by PenandFox.

Be like water, but a bit drier... Dad Hat

Item preview, Definitely not sad designed and sold by PenandFox.

Definitely not sad Baseball Cap

Item preview, Talented? Just a bit... man designed and sold by PenandFox.

Talented? Just a bit... man Dad Hat

Item preview, Definitely not easily shocked designed and sold by PenandFox.

Definitely not easily shocked Dad Hat

Item preview, Needless to say, I had the last laugh man designed and sold by PenandFox.

Needless to say, I had the last laugh man Baseball Cap

Item preview, Definitely not tired designed and sold by PenandFox.

Definitely not tired Dad Hat

Item preview, Don't cut your nose off, period... designed and sold by PenandFox.

Don't cut your nose off, period... Baseball Cap

Item preview, 75% or above at everything man designed and sold by PenandFox.

75% or above at everything man Dad Hat

Item preview, Honestly, I don't even try - man designed and sold by PenandFox.

Honestly, I don't even try - man Dad Hat

Item preview, Still waters run shallow sometimes... designed and sold by PenandFox.

Still waters run shallow sometimes... Dad Hat

Item preview, The pen is smaller than the sword... designed and sold by PenandFox.

The pen is smaller than the sword... Dad Hat

Item preview, Definitely not loved-up designed and sold by PenandFox.

Definitely not loved-up Dad Hat

Item preview, Definitely not weird designed and sold by PenandFox.

Definitely not weird Baseball Cap

Item preview, Beauty lies in the eye of the storm... designed and sold by PenandFox.

Beauty lies in the eye of the storm... Dad Hat

Item preview, Do not tread on old water designed and sold by PenandFox.

Do not tread on old water Baseball Cap

Item preview, I am a dancer and so so human... designed and sold by PenandFox.

I am a dancer and so so human... Baseball Cap

Item preview, Definitely not drunk designed and sold by PenandFox.

Definitely not drunk Dad Hat

Item preview, Definitely not secretly judging you designed and sold by PenandFox.

Definitely not secretly judging you Dad Hat

Item preview, Lukas Smug designed and sold by ThatJordo.

Lukas Smug Baseball Cap

Item preview, old man listens to music designed and sold by sosdesignn.

old man listens to music Dad Hat

Item preview, Smug Little Man designed and sold by TheSaltedSlug.

Smug Little Man Dad Hat

Item preview, Moth Giggles designed and sold by SoupedGuts.

Moth Giggles Baseball Cap

Item preview, Smug married gay - HUSBAND designed and sold by Smug Gay.

Smug married gay - HUSBAND Dad Hat

Item preview, Smug men collection designed and sold by PenandFox.

Smug men collection Dad Hat

Item preview, Smug frog - Anya Frogger designed and sold by CryptidArt.

Smug frog - Anya Frogger Baseball Cap

Item preview, Smug Cat designed and sold by sandpiperstudio.

Smug Cat Dad Hat

sandpiperstudio

Item preview, Golden Trump is a poor man's idea of a rich man, a weak man's idea of a strong man, and a stupid man's idea of a smart man. designed and sold by SubtleSplit.

Golden Trump is a poor man's idea of a rich man, a weak man's idea of a strong man, and a stupid man's idea of a smart man. Dad Hat

Item preview, Silly Cartoon man Collection No. 1 designed and sold by PenandFox.

Silly Cartoon man Collection No. 1 Baseball Cap

Item preview, Silly Cartoon man Collection No. 2 designed and sold by PenandFox.

Silly Cartoon man Collection No. 2 Dad Hat

Item preview, Superlative Man (#11 - Smuggest) [Create a set!] designed and sold by SolidEarthArt.

Superlative Man (#11 - Smuggest) [Create a set!] Baseball Cap

Item preview, Pepe Aesthetics designed and sold by MousMuse.

Pepe Aesthetics Dad Hat

Item preview, Smug Man with New Neck Brace for Insurance Fraud designed and sold by Naux | Design & Illustration.

Smug Man with New Neck Brace for Insurance Fraud Dad Hat

Naux | Design & Illustration

Item preview, Pepe the Frog Meme designed and sold by Asutip.

Pepe the Frog Meme Baseball Cap

Item preview, Smug Jet Tower Man (Artwork by Shend) designed and sold by Hoorahville.

Smug Jet Tower Man (Artwork by Shend) Dad Hat

Item preview, Moped wanker - funny, humour, joke - smug male on a scooter designed and sold by UKVanlife.

Moped wanker - funny, humour, joke - smug male on a scooter Dad Hat

Item preview, Cigar Straw Man – Off-White POD Print for Dark T-Shirts designed and sold by JonelCrafts.

Cigar Straw Man – Off-White POD Print for Dark T-Shirts Baseball Cap

Item preview, Cigar Straw Man – Black-Ink POD Print for Light T-Shirts designed and sold by JonelCrafts.

Cigar Straw Man – Black-Ink POD Print for Light T-Shirts Baseball Cap

Item preview, That’s None of My Business | Meme-Style Cartoon designed and sold by MyFashionDreams.

That’s None of My Business | Meme-Style Cartoon Dad Hat

MyFashionDreams

Item preview, Cat Dad Appreciation Day Greeting with Proud Man and Ginger Cat Royalty designed and sold by Places On Earth.

Cat Dad Appreciation Day Greeting with Proud Man and Ginger Cat Royalty Dad Hat

Places On Earth

Item preview, Charming and Supreme: The Chad Effect designed and sold by TeeGrit.

Charming and Supreme: The Chad Effect Baseball Cap

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