Jae’s Boxing Day Boxers Conundrum

It’s Boxing Day, and while most people are slumped on the sofa trying to remember what day it is, I find myself standing in the bathroom, staring at my reflection in a sad pair of pants and wondering when exactly underwear became complicated.  

This all started a few weeks ago when I realised every pair of boxers I owned had crossed that invisible threshold between “broken in” and “biodegradable.” The elastics were tired, the fabrics were translucent in places that should never be translucent, and one brave pair was held together largely by nostalgia.  

Ordinarily, Christmas is when the universe fixes such problems. You behave all year, drop a few unsubtle hints, and then: voilà! Someone drops a multi-pack of “essentials” under the tree. But, of course, this year was different. I unwrapped sweatpants, a couple of books, and a “funny” mug. No socks. No pants. Just vibes.  

I knew before then, that I was on my own in this endeavour. And so, like any man in his forties facing a crisis between his laundry and his wallet, I opened my laptop and typed “best men’s boxers UK”. A phrase that only gets searched when desperation is in the air.  

At some point, underwear for men stopped being simple. It used to be easy: you had your M&S multipack and got on with your life. Now every brand has discovered “performance.” They talk about “technology,” “airflow,” and “dynamic stretch” as if I’m planning to run a triathlon rather than just walk the dog and make coffee.  

Meanwhile, women’s lingerie remains a whole mood.. decadence, lace, power, allure. Men’s underwear, on the other hand, is basically PPE. No seduction, no flair, no mystery. Just sweat-wicking practicality.  

There’s a cruel imbalance in the underwear market: women buy lingerie to feel something; men buy boxers to stop feeling something. Namely chafing.  

And maybe that’s why we end up buying whatever multipack is closest to the till, until one day we realise our pants are more holes than fabric.  

The results of my internet search were both promising and horrifying.  

Pages upon pages of Adonis like men gazing moodily into middle distance wearing boxer briefs that look more like triathlon gear than underwear. Reviews claiming they “changed my life” or “made me feel confident again.” Honestly, if a pair of pants is doing that for you, good for you, champ, but I just want to get through a day without feeling like my thighs are at war.  

Still, curiosity got the better of me. I picked three highly reviewed brands: Step One, Randies, and Crossfly. I ordered a couple of each and paid in full; no adverts here. If influencers can review electric toothbrushes with scientific precision, I could surely take three pairs of boxers for a two-day test drive…

The Test Protocol  

To keep this robust, I set up identical testing conditions for every pair.  

- Day one: Workshop duty. Physical movement, light lifting, and the kind of bending and crouching that separates the strong seams from the lies.  

- Day two: Normal home day, desk work in the morning, dog walking in the afternoon, and a steady stream of coffee-fuelled trips upstairs.  

In total, about 20 hours of wear per pair. Enough to reveal if something rides up, rubs, or wrinkles in the wrong spots. And, because transparency matters, I will admit that all secondary testing involved the “no trousers walk-around” test, because no one should judge comfort through denim.  

 

Step One: great idea, but too noisy 

Step One’s marketing reads like the Apple keynote of the underwear world. Sustainable bamboo, “UltraGlyde” technology, anti-chafe innovation. You half expect them to sync with your iPhone. Out of the packet, they felt great: silky, stretchy, and with the promise of comfort.  

And they do deliver… sort of. No creeping up the leg, no waistband drama, and no feeling like you’re being gently garrotted by your own clothing; all big wins. But they lack one major feature: an internal pouch. Everything’s left to free-ball it in a loosely governed democracy, and while that’s fine standing up, it can get a bit too… communal when seated.  

Then there’s the noise. My chunky thighs, when left unchecked, usually generate only a faint hum of friction. In Step Ones, however, I discovered an entirely new sound, a low “swish-swish” with each step, like corduroy and a tarpaulin had a baby. It’s not loud enough to be embarrassing but just audible enough to make you weirdly self-conscious. It’s like being followed by your own sound effects.  

For pure comfort, 8/10. For confidence in silence, maybe a 4.

 

Randies: stylish chaos  

Randies are the cool kid’s boxer. The website oozes style with bold colours, sharp branding, pouches that promise support, and a marketing tone that sounds like it was written by a lad who owns too many candles. They look superb: great cut, soft waistband, and the kind of flair that makes you almost proud to fold your laundry.  

And for the first hour, they’re heavenly. The pouch keeps everything where it should be, and the fit feels athletic in a good way! Supportive, gently compressive, borderline heroic.  

Then, slowly, it all unravels. By lunchtime, they start to migrate north. By mid-afternoon, they’re practically making a break for freedom. I found myself doing subtle readjustments that were anything but subtle. If you’ve ever tried to discreetly fix your boxers while in public, you’ll know the mental gymnastics involved: bend a little, cough a bit, hope no one’s watching.  

By the end of day one, I was ready to demote them to the emergency drawer; the place where old pants go to die but still see action when you forget laundry day.  

The easy access pouch? Great. The comfort? Fleeting. It’s like dating someone stunning who then eats noisily. You realise looks aren’t everything.

Crossfly: boujie brilliance  

Finally, the underdog: Crossfly. I’ll be honest, they didn’t scream masculinity out of the packet. Aesthetically, there’s something a touch... boutique about them. The kind of underwear that comes in a box with tissue paper rather than plastic wrap.  

I half expected them to smell faintly like sandalwood and start a welcome conversation about mindfulness. Still, I put them on: inside out, naturally, because mornings and I have an ongoing feud. And by the time I realised, it was too late. The tag was already carving my lower back like a tiny tattooist made of nettles.  

Despite that rocky start, they were a revelation. Soft, breathable, and properly supportive thanks to that well-placed pouch. The design gets full marks for keeping everything organised without compression or overheating. These are boxers designed by someone who clearly has thighs, and my thighs were grateful.  

The fit was slightly on the snug side, particularly in the leg openings, but never to the point of circulation issues. The pouch itself feels engineered rather than just sewn on, which might explain why they’re the only pair that survived the full two-day test without a single adjustment.  

I even caught myself doing that small post-shower “which pair shall I honour today?” moment and picking the Crossfly ones out of choice, which says everything.  

The winner (by a comfortable margin)  

After thoughtful deliberation (and a mild existential crisis), Crossfly comes out the winner. They look decent, feel properly engineered, and after two full days of wear, I didn’t hit my usual allergy to discomfort. Step One gets runner-up for its lovely softness but loses points for the swishy soundtrack. Randies finishes last. All style, very little stamina.  

So, what have I learned? That men’s underwear is a labyrinth of false promises, and that any marketing phrase containing “cloud-soft” or “freedom fit” should be treated with suspicion. But also, that investing in decent boxers is worth it, if only to avoid those small, daily existential groans as you sit down and regret your choices.  

If I were wise, I’d bulk order Crossflys and be done for a few years. That would be the adult thing to do: buy once, buy right, and move on. But my car currently has more lights flashing on the dashboard than a Christmas tree having a seizure, and common sense isn’t exactly on brand for me.  

So, will I buy more? Yes. Will I still procrastinate for another six months until I’ve run out? Absolutely. Because some traditions, like Boxing Day leftovers and questionable life choices, are sacred. That and I still have no idea how much car repairs are going to cost me…