Most guys don’t wake up excited about buying underwear. It’s usually one of those things you pick up when your drawer starts looking tired or when a favorite pair finally gives up. So when a brand manages to make underwear feel even a little interesting, it’s worth paying attention.
That’s where On That Ass enters the picture.
Instead of selling endless styles and collections, the brand has built its reputation around one main idea: deliver a new pair of boxer shorts to your door every month through a subscription. Simple concept, but surprisingly effective. And judging by how often the name pops up in conversations about subscription underwear, a lot of people are clearly curious about it.
So what’s actually special about these boxer shorts? And are they any different from the pairs you’d normally grab off a store shelf?
Let’s break it down in a more practical, real-world way.
First Things First: How They Feel
Comfort is non-negotiable when it comes to underwear. If something feels scratchy, stiff, or too tight, it doesn’t matter how good it looks.
On That Ass boxer shorts are made mostly from cotton, with a small amount of elastane mixed in. That combination is pretty popular in modern underwear, and for good reason. Cotton keeps things breathable and soft, while elastane adds stretch so the fabric moves when you move.
In everyday use, this means the boxer shorts feel flexible rather than rigid. You can sit, walk, bend, or lounge without constantly adjusting. They don’t feel heavy, but they also don’t feel paper-thin. It’s that middle ground most people want but don’t always get.
After a few washes, they generally stay soft too, which isn’t always the case with cheaper underwear that tends to roughen up over time.
The Fit: Snug Without Feeling Tight
Fit is where a lot of underwear brands fall short. Either things are too loose and start sagging, or they’re too tight and feel restrictive.
The boxer shorts from On That Ass aim for a close, supportive fit without squeezing. The waistband has enough elasticity to stay in place, but it doesn’t dig into your skin. The legs sit at a comfortable length, which helps prevent riding up during the day.
One thing many people notice is that the boxer shorts keep their shape. You don’t get that stretched-out look after a few wears, which makes a bigger difference than it sounds.
It’s the kind of fit that fades into the background — and that’s usually a good sign.
About Those Designs
This is where On That Ass separates itself from plain, everyday underwear brands.
Instead of sticking to only black, grey, and navy, they release new designs each month. Some are subtle with simple patterns, others are loud and playful. You might get something minimal one month and something bold the next.
Not everyone loves surprises, but for a lot of subscribers, that unpredictability is part of the appeal. It keeps things from feeling boring.
The important part is that the designs don’t change the actual structure of the boxer shorts. No matter what the print looks like, the fit and fabric stay consistent.
How the Subscription Changes the Experience
Buying underwear usually happens in bursts. You realize you need new pairs, buy a pack, and then forget about it for months or even years.
On That Ass flips that habit.
You sign up once, and a new pair shows up every month. The first pair is offered as a free trial, so you can test the quality before committing. After that, the subscription runs automatically unless you decide to cancel.
For some people, this feels unnecessary. For others, it’s incredibly convenient. You slowly replace old underwear without thinking about it. Your drawer gradually upgrades itself.
There’s also something oddly satisfying about knowing a fresh pair is on the way each month, even if it’s something small.
Are They Built to Last?
Comfort is great, but durability matters just as much.
The cotton-elastane blend used by On That Ass tends to hold up well with regular washing. The fabric doesn’t easily lose its stretch, and the colors usually stay solid if you follow basic care instructions.
Seams are stitched cleanly and don’t feel bulky. That reduces friction and also helps prevent early wear in high-stress areas.
You’re not buying disposable underwear. These are meant to be worn repeatedly over a long period, which is what you’d expect from a mid-range subscription brand.
Who Will Probably Like These
These boxer shorts make the most sense for guys who value comfort and don’t enjoy shopping for basics.
If you like variety and don’t mind being surprised by designs, the subscription model can be fun. If you prefer choosing every single color and pattern yourself, it might feel limiting.
They’re also a decent gift idea. Since the first pair is free and sizing is straightforward, it’s a low-risk way to introduce someone to the brand.
Subscription vs. Store-Bought Underwear
With store-bought underwear, you get immediate control. You choose exactly what you want, when you want it.
With On That Ass, you trade some control for convenience.
You don’t browse. You don’t compare. You don’t remember to restock. You just receive a steady stream of new boxer shorts over time.
Neither option is objectively better. It comes down to how you prefer to shop.
The Bigger Picture
The success of On That Ass isn’t really about boxer shorts alone. It’s about fitting into modern habits.
People subscribe to music, movies, food kits, grooming products, and now underwear. The idea of automating small parts of life is becoming normal.
This brand simply applied that idea to something most people don’t enjoy buying.
So, Is It Worth Trying?
On That Ass boxer shorts aren’t trying to reinvent underwear. They’re focusing on getting the basics right: soft fabric, comfortable fit, and consistent quality, wrapped in a convenient subscription model.
If you’ve ever thought, “I hate shopping for underwear,” this service makes a lot of sense. And with the free first pair, there’s very little downside to seeing what the fuss is about.
Sometimes, the best upgrades are the quiet ones — the ones you stop noticing because everything just works.