Style -- 13 hours ago
The Best Men's Underwear | A Gentleman's Guide to What Goes Underneath
Choosing good underwear is an exercise in quiet discernment. The best pieces balance softness with structure and feel dependable without drawing attention to themselves.
- Words: Rupert Taylor
The best underwear for men is not the kind you notice. That is the first and perhaps only serious truth in this entire saga. The truly great pairs never demand your attention. They do not chafe, ride up, roll down, twist, pinch, or attempt an unsanctioned relationship with your inner thigh. They simply exist, quietly, doing vital diplomatic work between you and your trousers.
Unfortunately, most men learn this only by contrast. We grow up in multipacks, suffer through student years in greying cotton, dabble briefly in novelty prints, and then, at some point in early middle age, realise we are essentially high-functioning adults in every area except the one that touches us most intimately for the longest amount of time each day.
So I decided to fix that. Or at least understand it.
What began as a modest “I should probably buy some decent pants” turned into a months-long investigation into the best underwear for men across everyday wear, performance, modern comfort, heritage luxury and designer excess. I have worn more fabrics than a sofa showroom. I have become uncomfortably familiar with the word “modal”. I have opinions about pouch architecture.
This, then, is not a listicle. It is a long, honest, slightly unhinged piece of field reporting from the front lines of men’s underwear.
Everyday Basics | Finding The Best Underwear For Men
I started with the basics. The underwear I could wear to work, to the pub, on a flight, or while pretending to focus on a spreadsheet.
The first real turning point came with Mack Weldon. Their boxer briefs have been quietly crowned “best overall” so many times in American reviews that I approached them with suspicion. Anything described as “the iPhone of pants” is usually dreadful.
And yet.
Their AirknitX fabric manages that rare trick of feeling light without feeling flimsy. It wicks moisture, which is a polite way of saying it will not punish you for existing on a humid Tube. It has odour control, which we shall not unpack further. The pouch is supportive without looking like a structural engineering project. Mostly, though, you put them on in the morning and you don’t think about them again. That, to me, is the mark of great everyday underwear.
But before we get lost in innovation, we have to acknowledge the baseline, Calvin Klein. The Cotton Stretch and microfibre boxer briefs are still the default answer to the question “What are you wearing?” in every mid-tier department store and teenage bedroom. They are not perfect. They are not miraculous. But they are reliably soft, lightly elasticated, decently cut, and reassuringly familiar.
Calvin Klein is the metric system of underwear. Even if you never wear it, you need it as a reference point.
The first time I truly understood the gap between “fine” and “oh, that’s different” was when I tried Tommy John. Their “Second Skin” range is made from micro-modal so smooth that I briefly checked the label to see if it was legal. It has that uncanny “second skin” sensation marketing people love to promise and almost never deliver. The waistband stays flat and unruffled. The legs do not bunch. You never have to do that tragic little shuffle men do when their underwear has migrated somewhere it shouldn’t, but they are in public and too proud to admit it.
Tommy John is not the kind of brand you buy by mistake in a supermarket. It is the brand you buy when you finally admit that perhaps, just perhaps, a few extra pounds spent here might be more life-improving than yet another shirt.
Day to day, these three became my control group. Calvin for the baseline, Mack Weldon for the “I have a day ahead of me and I’d rather not know I’m wearing anything”, Tommy John for the “I intend to be kind to myself today” feeling.
Performance And Sport | When The Best Underwear Has An Actual Job
Then there are the days when your underwear has to work for a living. Gym days. Run days. Days when you agreed to something described as “a hike” by someone suspiciously fit. On those days, the best underwear for men stops being about softness and starts being about survival.
Enter Saxx and its BallPark Pouch. If you have never seen it, imagine a small, soft, internal hammock designed to keep everything separate, supported and under control. It sounds absurd. It looks a bit absurd. It works brilliantly.
I wore Saxx on a summer run that, historically, would have ended in a deeply personal vendetta against my own clothing. Instead, everything stayed where it should. No rubbing. No sticking. No moments of pure existential rage at mile four. Saxx has become the one I automatically reach for when I know I will be active and would rather not think about the consequences.
Lululemon, meanwhile, appears in almost every “gym underwear” conversation now, and not without reason. Their “Always in Motion” boxer briefs are that rare technical garment that doesn’t feel overthought. Lightweight. Quick drying. Enough support to stop the chaos, not so much that you feel vacuum-packed. They are the silent partner to your over-ambitious training programme, quietly compensating for your choices.
Between Saxx and Lululemon, I learned something important. The best underwear for men is situational. The pair that feels miraculous under tailoring is not necessarily the pair you want on a treadmill. Trying to force one pair to “do it all” is like expecting your accountant to DJ your wedding.
Quiet Luxury | The Best Men’s Underwear When You Care About Fabric
At some point in this odyssey, I drifted away from performance wear and into the more dangerous waters of “modern luxury basics”. This is where you find the brands that talk about lyocell and modal and sustainability, and where the phrase “Scandinavian design” appears so often you begin to suspect the entire region has been secretly designing our pants for years.
The star here is CDLP. If Mack Weldon is the engineer and Calvin Klein is the diplomat, CDLP is the architect. It makes underwear that looks like it was designed by people who own mid-century furniture and know their barista’s surname.
Their signature fabric is lyocell, soft, cool, slightly silky, derived from wood pulp and therefore easy to talk about at dinner parties. The cuts are minimal. The colours are cultivated, muted greens, navies and greys that feel more “considered capsule wardrobe” than “three for two”. There are no big logos. No loud waistbands. Just exceptionally comfortable, well-cut trunks that make the rest of your drawer look faintly tragic.
CDLP quickly became my answer to the question of what I would say if a Gentleman’s Journal reader asked me for the best underwear for men that feels luxurious without being silly. I would say this.
On the more pop-cultural side of things sits Skims. I wanted to dislike it. Truly. It has all the makings of a brand I would roll my eyes at, celebrity association, social media dominance, hype. Then I tried the men’s modal boxer briefs and had to admit they are outrageously comfortable. The fabric is soft in an almost implausible way. The cut is snug but not aggressive. The pouch is supportive without shouting about it. There is a sort of technical hug quality to them.
Skims, for better or worse, is the brand I reach for on days when my body and brain both feel slightly fragile and I want everything to be as forgiving as possible.
Bombas approaches the same category with a more wholesome angle through very soft fabrics, clever seams, excellent comfort, and a buy-one-give-one model where they donate a pair for every one you purchase. Wearing Bombas makes you feel like a decent person, and, crucially, like a comfortable one.
At the more aesthetic edge of things we find Ron Dorff. Imagine if a Scandinavian gym hired a French creative director. Clean lines. Good cotton. Slightly athletic cuts. Branding that says “DISCIPLINE” and actually makes you want to live up to it. There is a quietly sexy, athletic energy to Ron Dorff that makes it one of the best underwear choices for men who would like their pants to say “I own a decent set of dumbbells and a well-lit bathroom mirror”.
And then there’s Bluebuck, which takes sustainability seriously but packages it with reassuringly masculine branding. Organic cotton, durable construction, the sort of trunks you might plausibly wear while chopping wood, even if your real daily challenge is navigating Pret at lunchtime. Bluebuck is what you choose when you want to do right by the planet without needing to talk about it too much.
Heritage And High Fashion | Underwear For Men Who Like A Bit Of Theatre
Of course, not all underwear exists purely to be invisible. Some of it exists to satisfy the part of our brain that enjoys unnecessary excellence and, occasionally, outright theatre.
At the refined end of that spectrum is Sunspel. Sunspel is the quiet British heritage brand that has been making exquisite basics since before most of our wardrobes existed. Their jersey trunks and woven boxer shorts are exercises in restraint, perfect cotton, thoughtful cuts, subtle details. If CDLP is modern Scandinavian luxury, Sunspel is classic English understatement. The fact that James Bond has worn their underwear is simply a bonus flourish.
Then there is Hanro, the Swiss master of calm. Hanro excels in fabrics that make you question everything you thought you knew about cotton. Mercerised cotton, silk-modal blends, even cashmere-silk for men who believe their thighs deserve the same respect as their neck. Hanro underwear is not about impact. It is about an ongoing, entirely private sense of “oh, that’s nice”.
At the top of the mountain sits Zimmerli, a Swiss brand so indulgent it borders on satire. Often described as some of the most luxurious underwear in the world, Zimmerli uses extremely fine cotton and silk, cut and sewn by hand, to create garments you will feel guilty hiding under jeans. It is ridiculous. It is unnecessary. It is magnificent. It is also probably the best underwear for men who have solved all their other problems and are now just optimising for pleasure.
On the more extrovert side are Versace and Tom Ford. Versace underwear is exactly what you think it is, bold prints, big logos, baroque waistbands announcing Medusa to anyone in a five-metre radius. Underneath the drama, the fabrics are decent, the fits good, and the effect undeniable. These are not your everyday office trunks. These are “I am on holiday with ill intentions” trunks.
Tom Ford, by contrast, is all about controlled intensity. Sleek cuts. Excellent fabrics. Waistbands that let you know exactly who is responsible. Pulling on a pair of Tom Ford boxer briefs does not turn you into a different man, but it does make you walk around your bedroom with slightly different energy.
So Which Is The Best Underwear For A Gentleman?
After all of this, the testing, the travelling, the occasional regret, what would I actually recommend?
If you want a simple, boring answer, it’s this. You need different underwear for different situations. Mack Weldon or Tommy John under a suit. Saxx or Lululemon for the gym. CDLP, Skims, or Ron Dorff for days when you care about how things feel as much as how they look. Sunspel or Hanro when you want to feel quietly superior. Zimmerli when you have completely lost perspective.
But if you forced me, at silk-covered gunpoint, to choose one brand that feels most appropriate for a Gentleman’s Journal reader as the “if you’re going to upgrade, start here” option, it would be CDLP.
Why? Because it sits at the intersection of everything that matters. Modern but not try-hard. Luxurious but not shouty. Technically impressive but not obsessed with its own technology. Sustainable in a way that feels intelligent rather than preachy. Underwear you can wear under a suit, under cashmere, on a date, on a flight, at a desk, in a life that aspires to be at least mildly curated.
The best underwear for men, in the end, is not about which logo you see in the mirror or which fabric sounds the fanciest. It is about how you feel for the twelve hours you forget you are wearing it. And if you can forget you are wearing something that well-designed, that soft, and that carefully made, then that, to me, is money very well spent.
Upgrade the drawer. The rest of your wardrobe will thank you.
