Hello and welcome to The Old Summers Home. Today I’m sharing our 5 funny men’s boxers/ briefs designs that make the perfect gift for him. These are a huge hit and everyone gets a great laugh too!

Plus who doesn’t love underwear, especially for Valentine’s day, am I right? These became known as my Valentine’s Boxers because they are so very popular at that time of year! However, they can be a great gift idea for other occasions too!

Today I’m going to show you how to make these funny men’s boxers and the mistakes you need to avoid.

Funny Men’s Boxers Designs

Men’s Boxers are always at the centre of attention during special occasions, especially Valentine’s day! A few years back I had the most successful Valentine’s Day my little business ever had. Valentine’s boxers were a hit!

Here are my favourite designs that I think are epically hilarious!

Are you looking for a hilarious gift for him? These men's boxers will be sure to make him laugh. Learn how to make them at the old summers home! Shop our favourite men's boxers! #MensBoxer #FunnyGiftForHim #ValentinesGiftIdeasForHim #FunnyMensBoxers

Love them too? Grab your FREE designs below!

The Man. The Legend.

This a classic design that never gets old. It is most commonly seen on T-shirts but creates a whole new hilarious aspect when placed on a pair of men’s boxers, hahaha!

Caution. May Contain Nuts.

Funny and cute all the same time! This has to be one of my favourite Valentine gift ideas for him. These would be incomplete without the squirrel!

Pull Down In case of Emergency.

What is not laugh about with these? The bright yellow warning sign is such a fun idea too!

Property of _______(name of significant other)

When I first made my husband a test pair (I tested all my products on my family before selling to customers) I was not sure I should put these on my Business page. I have a great sense of humour but wasn’t sure how my audience would take it. Let’s just say these were a hit!

How to Make Funny Men’s Boxers

Have you ever wondered how to make these hilarious men’s boxers? Well, I have made tons of these and these are my best tips to ensure you provide quality boxers to your customers!

Where to find the perfect Mens Boxers

These Boxers are made by Gildan and are my favourite to use. They are affordable and a much better fit than others I tested. If you are selling men’s boxers or any other apparel make sure to always include a size chart so that your customers can ensure these personalized funny men’s boxers fit correctly the first time!

Choose your favourite Valentine’s boxers design.

Pick a design from our Freebies (Get yours below) or design your own. Whatever you choose I’m sure it will be funny!

Vinyl must be stretch!

Learn from my mistake and use Stretch vinyl! Boxers change their shape entirely when worn so ensure to use the highest quality of vinyl! My favourite HTV is the Siser Easy Weed Stretch.

Always make sure to mirror your image when using HTV. If you don’t your image and text will be backward when pressed onto your apparel.

Some people say Siser EasyWeed is hard to weed, personally, I haven’t had this trouble but you can warm up your sheets by placing them on your heat-press for a few seconds (DO NOT PRESS).

Use a light pad to help make weeding easier on the eyes!

Are you looking for a hilarious gift for him? These men's boxers will be sure to make him laugh. Learn how to make them at the old summers home! Shop our favourite men's boxers! #MensBoxer #FunnyGiftForHim #ValentinesGiftIdeasForHim #FunnyMensBoxers

Pressing the Valentines Boxers

  • Use a pressing cloth.
  • Pre-press boxers
  • Adequate pressure
  • Remove carrier sheet
  • Press for 15
  • Look for fabric lines in the vinyl
  • Test the stretch
  • When in doubt, press again


Visit our How to heat press apparel like a boss post for tips to make our funny men's boxers yourself. including tips and tricks to make heat pressing easier. A beginners guide to using a heat press.

See our how to heat press apparel post (coming soon!) for all the details to get the perfect press every time.

Shopping Valentines Gift For Him!

I don’t know about you but I love to laugh. Laughing makes life more fun, relieves stress and it is so good for the soul! My husband has a great sense of humour and we have a lot of laughs throughout the day.

If your significant other can share with you on some laughs you have to check these out!

Got Game Men's Boxers Available at Walmart. These funny boxers are perfect the guy in your life with a sense of humour.

These hilarious Got Game Men’s Boxers that are sure to make the hunter in your life smile. they have a full all-over print with a few different sayings.

Police line do not cross funny men's boxers from Walmart.

These police tape men’s boxers are a fun gift for him. The yellow is so bright, similar to our warning funny men’s boxers up above.


I like big bucks! Oh, my Gawd, Becky! After finding these I now officially have the song “Baby got back” stuck in my head so I had to spread the love haha.

Free SVG Files!

Love our men’s boxers and want to make your own? Grab our FREE SVG files and get crafting!

Trial & Error Of Making These Funny Men’s Boxers

Before you go, I just want to take a moment to come back to something I mentioned above.

If you are selling products to customers, you must test to ensure quality.

There was a lot of trial and error in making these, in fact, the first round of boxers I designed and made did not go to the public because I noticed a flaw in my design after testing them. Well, a few things actually.

  1. the font was too thin
  2. needed stretch vinyl
  3. needed more pressure
  4. needed a pressing cloth

Imagine if I had sold them to customers and after the first use they came apart?!? You do not want that to happen! Be sure to always test your products first!

Vinyl doesn’t last forever, of course, and there are care instructions you need to pass along to your customers in order to maintain the quality of your work. But most important of all, make sure you are producing quality items. Be sure to subscribe so you can get all my tips and tricks plus these FREE SVG files!

For more great crafts using a cutting machine check out our reverse canvas tutorial and our flip stir whisk mason jar set! There are many more crafts in our DIY Tutorials section too!

Thank you so much for coming today, I hope you enjoyed this post, learnt something new and had a good laugh! Be sure to check back soon for our How to heat press apparel post! See you soon!

Until Next Time;

Jenn Summers The Old Summers Home

Jenn Summers

The Old Summers Home