Fashionista Seeking Irony Pillows

'I need something to wear to a bankruptcy hearing.'

'Now that I've lost weight, I can't afford new clothes in my size.'

Middle-Age Superheroes

'I hate waking up with coffin hair.'

All it takes is a little willpower and a good metabolism...

'Have you any W fronts?'

"Wow, you look sexy today."

The Inventor of the Man Bun!

Buy One Get One Free Sign Outside Shoe Shop

"Do these puffy pants make me look less tyrannical?"

"I thought I put on my 'big boy' pants this morning but apparently they were my 'fire me' pants."

"I don’t know, honey – sort of makes you look like a blockhead."

"Gap... Tony Soprano fit"

"Look at these old clothes, Dylan! You know, tie-dye HAS made a comeback!"

"Apparently 'the vest' is making a comeback..."

Hoody Woodpecker.

"Apparently, he's well over 100 now."

"We're thinking of having your nose pierced."

Home for the Holidays

Luke Warm & Over E-Z: The World's Blandest Rappers.

"Does it say I'm a Wittgenstein scholar?"

"I'll only remove what's necessary...your gall bladder and the man bun."

Ugly sisters

"Wingtips - this is a white collar gang."

The latest fall fashion trends

"Everyone who cares about you is here, Frank, because we all feel it's time you quit wearing your baseball cap backwards."

"I don't want to look ridiculous at the clown convention!"

Holy cow. Holycow. Holycow. What? You won't believe the American hero coming to the cafe. Lady Gaga? Kanye? Elon Musk? A venture capitalist. Do I look greedy enough in this shirt? I weep.

'I couldn't decide what to wear to work so I just didn't go.'

"Mum, I can't find my camouflage jacket."

The Three Stylish Klansmen

As his hearing worsened, Larry had to buy louder and louder clothes.

I like your suit, to me it says 'management'

A Simple Guide To The Trump Combover

"We've been wearing our jackets wrong all these years."