When it comes to humor, sometimes the silliest topics make for the best laughs. And what could be funnier (or cheekier) than underwear jokes? These jokes may be a little “brief,” but they pack plenty of punchlines that will leave you grinning from ear to ear. Whether you’re looking for family-friendly gags, playful puns, or slightly cheeky humor, this collection of underwear jokes has something for everyone.
Underwear is something we all wear but rarely talk about—making it the perfect subject for lighthearted comedy. From silly one-liners about boxers and briefs to laugh-out-loud quips about laundry day, these jokes take something ordinary and turn it into pure comedy gold. They’re fun to share with friends, great for breaking the ice, and perfect for making everyday situations a little more entertaining.
In this article, you’ll find a wide variety of underwear jokes—from clean and kid-friendly to witty and slightly cheeky. Whether you’re looking for jokes for social media captions, party fun, or just to brighten someone’s day, this list will keep the laughs rolling.
So get ready to giggle, chuckle, and maybe even blush a little—because these underwear jokes are guaranteed to keep you in stitches (hopefully not in your underwear seams!).
Brief Encounters
I wore my briefs to court—they made a strong case.
Life’s too short for boring briefs.
That joke was brief… and supportive.
I made a brief appearance at laundry day.
Briefs: business in the front, wedgie in the back.
Some wear briefs. Legends wear confidence.
I don’t fold my briefs—I freestyle.
I’m feeling snug and punny.
Elasticity is a lifestyle.
It’s a brief world, after all.
Boxers or Bust
Real freedom starts with boxers.
My boxers are wilder than my weekend.
Loose fabric, looser morals.
I’m not lazy—I’m just boxer’d in.
That print? Pure chaos and confidence.
Boxer rebellion, but make it fashion.
These boxers speak louder than words.
Snug life? Nah, I live loud and loose.
Boxers: party below the belt.
They say size doesn’t matter—tell that to my boxer shorts.
Cheeky Business
My pants are cheekier than my jokes.
Let’s not split hairs—or seams.
Talk about a rear-ending punchline.
You crack me up—literally.
I’m two cheeks to the wind.
My sense of humor is full moon approved.
Booty calls? I respond with boxer briefs.
Pants: keeping cheeky moments PG since forever.
I came, I saw, I cheeked.
This joke’s got back.
Laundry Day Laughs
I fold laundry once a season—spring-ish.
My undies disappeared in the dryer vortex.
Clean underwear? Never met her.
My boxers are social—they mingle in the wash.
My undies live their best life in laundry limbo.
I sort by “hope” and “shrunk.”
Spin cycle? More like sin cycle.
Laundry day: the ultimate gamble.
My briefs came out emotionally wrinkled.
If underwear had feelings, mine would file complaints.
Superpant Powers
Every superhero starts with strong undies.
I put my pants on over my problems.
Capes are optional—briefs are not.
Elastic justice for all.
My briefs hold more secrets than Batman.
I don’t need armor—just reinforced stitching.
Kryptonite? No—wedgies.
Boxers by day, briefs by destiny.
Even Superman needed support.
I’m faster than a snap waistband.
Punderwear 101
I’m a pun-derwear enthusiast.
Brief humor is my full-time gig.
I like my jokes like my underwear—clean and clever.
That pun really hugged the punchline.
Elastic wordplay: flexible and fun.
That was a low blow… literally.
Puns that lift and separate.
No pant-line can hide this humor.
Seamlessly funny.
I’m stitched with wit.
Comfy & Punfident
Good undies = inner peace.
My waistband aligns my chakras.
I feel most powerful in cotton.
Stretch, breathe, repeat.
Namasté in my boxer briefs.
I inhale calm, exhale wedgies.
Comfortable underwear = peak adulting.
Zen and the art of waistband maintenance.
I find stillness between the seams.
Soft waistband, strong soul.
Romantic Undie-takings
Love is blind—but it sees panty lines.
I fell for you—and tripped on my thong.
He said he loved me, then saw my granny panties.
Cupid wears boxer-briefs.
I slipped into something uncomfortable: feelings.
Undies with hearts? Love me tender.
We matched—right down to the waistband.
You make my elastic snap.
We had chemistry—until laundry day.
He ghosted me… and took my socks.
Sock It to Me
My socks are in a committed relationship with my briefs.
Odd sock? Meet awkward underwear.
They disappeared together—love story or laundry crime?
Briefs and socks: the power couple of drawers.
My sock drawer holds secrets.
If socks go missing, blame the briefs.
Laundry: where relationships unravel.
Fold me once, shame on you.
My briefs have matching issues.
Sock puppet theatre, but make it cheeky.
Wedgie Woes
Friends don’t let friends wear tight pants.
That’s not support—it’s a silent scream.
The surprise wedgie: life’s cruel prank.
Elastic betrayal hurts the most.
I walked funny for a reason.
That ride was not amusement.
Wedgie therapy: $99/hour.
This joke chafes a little.
The fabric of failure.
- I sat on my self-respect.
Embarrass-Mint Condition
My underwear showed up before I did.
Sat down… and stood up single.
Accidentally flashed my polka dots.
Bent over—became the star of aisle 5.
When life gives you lemons… cover them.
My underwear called for backup.
Is it hot in here or is that my waistband failing?
Mooned accidentally, blushed eternally.
Elastic karma is real.
I wore confidence… until it snapped.
Pajamas & Panic
Pajamas: where underwear goes to hide.
I wear my feelings—and flannel.
Undies beneath PJs? Layered insecurity.
My pants said sleep, my body said dance.
Is it bedtime or breakdown time?
Who needs pants when you’ve got matching plaid?
Elastic dreams and polyester regrets.
My sleepwear is silently judging me.
Too snug to snore.
I woke up tangled in doubt and drawstrings.
Travel Under-wearabouts
I packed light—but not underwear light.
TSA judged my polka dots.
Airport undies = uncomfortable truths.
My suitcase holds more briefs than hopes.
I forgot toothpaste, packed 12 pairs.
Underwear: the real carry-on essential.
I left my dignity in Terminal 3.
Elastic doesn’t like turbulence.
My underwear went on vacation without me.
Jet lag, tight tag.
Party Pants & Disco Drawers
Shake your briefs like nobody’s watching.
My undies are louder than the DJ.
Pants dropped like the bass.
Confetti and chafing—what a night!
I boogied out of my waistband.
Disco balls, disco drawers.
This dance floor is cotton-lined.
I moonwalked too literally.
It was lit—so were my undies.
I came to party and forgot my pants.
At Home in Underwear
Pants? Where we’re going, we don’t need pants.
Home is where the elastic is.
Boxers are my work-from-home uniform.
Zoom waist-up, freedom waist-down.
My couch knows my polka-dot side.
These undies have been through all 8 seasons of my comfort zone.
I’m emotionally stitched to my loungewear.
Socks optional, shame not.
My AC and I share an intimate breeze.
Undies: the fabric of remote productivity.
Granny Panty Pride
More fabric, more feelings.
Granny panties: because comfort comes first.
Coverage you can trust.
My bloomers have Wi-Fi.
Elastic so good, it holds my childhood together.
These aren’t panties—they’re real estate.
Lace? No. Legacy.
Bold, beige, and beautiful.
I don’t chase trends—I chase coverage.
Granny called—they’re back in style.
Secret Undie-Gents
My briefs have top-secret compartments.
License to chill in boxers.
Spies wear briefs too—you just don’t know it.
My underwear’s got more intel than my browser.
I hide snacks. What’s your superpower?
This message will self-destruct in 10 elastic snaps.
Stealthy… except for the neon.
I blend into crowds with cartoon characters.
Brief encounters of the stealthy kind.
Double-O-Drawer.
Kids Say the Brief-est Things
“Why are your pants sleeping?” – 5-year-old.
My kid wears undies on his head. No questions.
Potty training = betrayal in cotton form.
“Mommy, why do your panties scream?”
They outgrow everything—except chaos.
I bought 10 packs. We still ran out.
My child picked undies with dinosaurs. Respect.
Laundry looks like a Crayola box exploded.
“These smell weird.” “They’re clean!”
Tiny pants, huge drama.
Every Day’s a Brief Holiday
Monday: matching socks and matching briefs.
Tuesday: surprise thong.
Wednesday: laundry panic.
Thursday: polka dots for courage.
Friday: going out briefs—sparkly and sassy.
Saturday: boxers with pizza slices.
Sunday: no shame, no pants.
Valentine’s = lace and regrets.
Halloween = glow-in-the-dark ghosts.
Christmas = reindeer wedgies.
The Gift of Gitch
Gave boxers. Got blank stares.
Nothing says “love” like novelty underwear.
They unwrapped a wedgie.
“You got me… a 3-pack?”
Red hearts, blue regret.
Lace lingerie: the emotional gamble.
My gift screamed “last minute.”
Underwear subscription: the gift that keeps riding up.
Socks + undies = family traditions.
Gift-wrapped giggles.
FAQs
1. What are some funny underwear captions for Instagram?
Try: “Wearing confidence… and a little cotton,” or “My mood? Boxers and bad choices.”
2. Can I use these underwear jokes for a birthday card?
Absolutely! They pair well with gift-wrapped briefs or socks.
3. Are these jokes safe for kids?
Yes! They’re cheeky but clean. PG-level puns for all ages.
4. What’s the funniest type of underwear to joke about?
Granny panties, novelty boxers, and glow-in-the-dark briefs are comedy gold.
5. How do I make my own underwear puns?
Think: fabric + emotions + awkward moments. Then fold in some wordplay.
6. Can I print these puns on underwear or merch?
Yes! They’d be hilarious on shirts, socks, or even boxer tags.
7. What’s a good gag gift involving underwear?
Undies with quotes like “Brief Encounter” or “Cheeky but Classy.”
8. Is it weird to name your underwear?
Only if they answer back.
9. Are boxer briefs funnier than thongs?
Boxers are roomier for jokes, but thongs have more edge.
10. Where can I find more themed puns like this?
Right here on PunsPlanet.com — the internet’s favorite place to hang out (like laundry).
Conclusion
From wild prints to weird wedgies, underwear is universally funny. It’s the great equalizer—everybody wears it (hopefully), and everyone’s got a story or two that ends with, “and then my pants split.”
These jokes may go below the belt, but they lift the spirit. Because when life gets heavy, the best thing you can do is laugh it off—and maybe adjust your waistband.
So whether you’re lounging in boxers, rocking silky briefs, or living that granny panty life, remember: you’re always one joke away from a better day.
Share the Laughs & Stay Cheeky!
If these puns made you snort-laugh or tug at your waistband in solidarity, share the giggles!
👉 Comment, share, and visit PunsPlanet.com for more pun-derwear brilliance, one cheeky category at a time!
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