17 Jokes About Underwear

Puns

Updated on: Jul 06 2025

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Why did the underwear blush? It saw the elastic waistband!
My underwear told me a joke, but it was a brief encounter – it left me in stitches!
Why did the underwear apply for a job? It wanted to get a brief career!
Why did the underwear break up? It just couldn't hold things together anymore!
Why did the underwear go to school? It wanted to be a smarty pants!
Why did the underwear go to therapy? It had too many issues to brief about!
Why did the underwear go to therapy? It had too many issues to brief about!

Undie-mirable Situations

You ever notice how underwear has a mind of its own? One day it's all snug and cozy, the next it's playing hide-and-seek in places you didn't even know existed. I'm convinced my underwear has a secret agenda, like it's plotting to escape and start a new life without me. Maybe it just wants to be free, you know, pursue its dreams of being a superhero cape or something.

Brief Encounter

I bought these new fancy briefs the other day – you know, the ones that promise to enhance your confidence and make you feel like a superhero. Well, let me tell you, I put them on, struck a pose in the mirror, and immediately tripped over my own feet. Turns out, feeling like a superhero is not compatible with walking gracefully. Note to self: superheroes need capes, not briefs.

Fashion Faux Pas

Fashion experts say that your underwear should match your outerwear for a seamless look. Honestly, if I followed that advice, I'd have to wear camouflage underwear to match the chaos that is my life. Imagine me at a job interview, confidently striding in, and then accidentally dropping my pen, only to realize I'm also revealing my army-print undies. Talk about making a statement.

Elastic Fantasia

Underwear elastic is a fascinating thing. It starts off tight and supportive, but after a few washes, it turns into this rebellious teenager, refusing to stay where it's supposed to. It's like, I'm not conforming to society's standards, man! My underwear's elastic is on a journey of self-discovery, and apparently, that journey involves constant sagging.

Undercover Operations

Ever put on underwear and feel like you're hiding a classified document? There's this moment of secrecy and importance, like I'm some undercover agent carrying vital information in my underpants. If anyone asks, just tell them I'm on a mission for freshness and comfort.

The Mystery of the Missing Sock

You know how socks always disappear in the laundry? Well, I think my underwear has joined a secret society with the missing socks. They're probably having a wild party somewhere, laughing at us as we futilely search for them. I can almost hear them chanting, No matching pairs allowed!

Laundry Day Dilemmas

Laundry day is like a battlefield, and my underwear is the unsung hero that never makes it out unscathed. It's seen stains that would make a crime scene investigator blush. I feel sorry for it, honestly. It's been through more wars than some countries, and here I am, folding it up like it hasn't been through a battle against spaghetti sauce and coffee spills.

The Sock-Underwear Alliance

I've figured it out – socks and underwear are in cahoots. Socks disappear, and underwear plots its great escape. It's like a coordinated effort to keep us guessing. Maybe they have their own version of a United Nations meeting where they discuss world domination through stealthy disappearance.

Underwear Wisdom

You ever notice how, when you're in a rush, putting on underwear suddenly becomes the most complicated task in the world? It's like my brain goes into slow motion, and I transform into an underwear acrobat. I've come to the conclusion that the key to life's success is mastering the art of putting on underwear gracefully. If you can conquer that, you can conquer anything.

Brief Briefings

Why do they call it briefs? There's nothing brief about the amount of time I spend trying to find a comfortable position once I've put them on. It's like I'm participating in a secret gymnastics competition, and my underwear is the judge, silently scoring my routine from the shadows.

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