Gift styling inspiration. Packaging and accessories shown are not included.
Buying someone a funny shirt is a small test of how well you know them.
There’s the joke that makes you laugh—and then there’s the one they’ll happily wear to brunch. Ideally, you find the overlap.
You can probably picture the moment you’re hoping for: he opens it, reads it, pauses, and looks up at you with that smile. You got him.
If you’re looking for funny gifts for gay men, that’s a useful place to start. Think about the particular man you’re buying for: his taste, his humor, and the little things you’ve noticed.
Here’s how to choose something that feels personal and earns a place in his wardrobe.
1. Start with the joke you already share
Think about what he sends you. The screenshots. The running commentary. The very specific reason he suddenly became interested in hockey.
Those details give you a better starting point than browsing every gift category on the internet.
Look for a reference he already enjoys. A sports double meaning might be perfect for someone who appreciates a raised eyebrow. A flirty line might suit the friend whose finest opening move is temporarily forgetting how sentences work.
The question to ask is simple: would he enjoy being in on this joke?
If you can immediately imagine him sending a picture of the shirt to someone else, you may be onto something.
2. Picture where he would actually wear it
Before choosing the design, imagine an ordinary outfit of his.
Does he reach for black tees and jeans? Does he like a crisp white shirt under an open layer? Is his wardrobe full of illustrations, or does one well-placed line usually do the talking?
Choose a color and style that can join what he already wears. There’s room for a little surprise, especially when it connects to something you know he loves.
Try picturing the shirt on him three weeks after the occasion. A coffee run. Drinks with friends. A relaxed evening with you.
That’s the version of the gift worth shopping for.
For outfit inspiration, our guide to styling a graphic tee for a night out puts five combinations together.
3. Choose the level of flirtation he’ll enjoy
A joke between partners can land differently from one given by a friend—or opened in front of a room full of relatives.
Consider the relationship and the setting. You want him to enjoy the gift without having to manage an uncomfortable explanation.
There’s plenty of room between a gentle wink and a very clear invitation. Pick the place where his sense of humor lives.
A few PPA examples:
For the charmingly awkward flirt
If I Seem Awkward follows its introduction with “You’re Probably My Type” and a small “Please Proceed.”
A possible choice for someone who already laughs about their own flirting style. If you’re giving it to someone you fancy, consider that it may also do a little communicating on your behalf.
For the friend with a very specific fall forecast
Seasonal Outlook turns gray sweatpants season into a vintage weather advisory.
Think of the person who will understand the forecast immediately—and happily wear it.
For someone who appreciates financial double meanings
Bear Market pairs its title with “Bullish on Men.”
Choose it because he enjoys the wordplay or identifies with the reference. Let him decide which labels feel like his.
4. Do a little homework on fit
Sizing is worth a moment of attention. A shirt he feels comfortable in has a much better chance of becoming a favorite.
If he’s your partner and you have access to a tee he loves, compare its measurements with the listing’s size guide, following the guide’s measuring instructions. Notice whether he likes a closer fit or extra room.
For a friend, asking is perfectly reasonable: “I found something for you—what size do you usually like in a tee?”
The design can still be a surprise. You don’t need to turn sizing into an undercover operation.
Check the current return policy and processing information before ordering, too, particularly if the gift is needed for a specific date.
5. Add the sentence only you could write
The easiest way to make a gift more personal is to say why you chose it.
Keep it short:
“This reminded me of your extremely detailed hockey commentary.”
“For your next attempt at making the first move.”
“Saw this and immediately wanted to hear your laugh.”
Use your own words. A small, specific note gives the joke somewhere affectionate to land.
The best part is feeling noticed
We hope a PPA shirt brings a little humor into someone’s day. As a gift, it can carry something else, too: the pleasure of knowing someone paid attention.
You remembered what makes him laugh. You noticed what he likes to wear. You found something you wanted him to have.
That’s a lovely thing to give.
Find the shirt that makes you think of him at Position Pending Apparel.
Wear Your Type.