I’m a 54-year old Y-front aficionado – here’s what happened when I tried some new underwear

Briefs encounter: Nick Harding tries a new look
Briefs encounter: Nick Harding tries a new look - Andrew Crowley

Underpants are the most personal thing we wear. Yet most of us pay zilch attention to them, sticking with one style all our lives, often the same brand, the same material and the same colour. We cling on to our favourites until they disintegrate. Many of us don’t even buy our own and rely on the charity of birthdays and Christmas gifts instead.

Personally, I live safe in the knowledge that should I be involved in a road accident, whatever the day, when the paramedics cut off my bloodied jeans they’ll find a nice pair of black Marks and Spencer microskin hipster trunks. I wear nothing else.

This attitude to pants is not unusual, as personal stylist Nick Hems explains: “Pants get forgotten. I often ask my clients, ‘Where’s your underwear at?’ and mostly they don’t think too much about it beyond what they always wear. They generally go for black or grey. But underpants are one of the most important garments you own.

“You wear them every day so why not consider wearing something that makes you happy, rather than wearing something because it’s functional?”

Indeed, a change of underwear can change your life.

Men's underwear is big business
Men's underwear is big business - WENN Rights Ltd / Alamy

Hems continues: “I’ll often throw in something a client hasn’t tried and sometimes they come back and say, ‘You have changed my life, I’ve gone out and bought seven pairs of these.’ Men underestimate the effect underwear can have. Getting it spot on can have a massive impact on how you feel about yourself every day. Brands are beginning to wake up to this and are introducing more variety and styles.”

The latest brand to dip its toes into this untapped market is Kim Kardashian’s Skims, which recently expanded its $4bn (£3bn) range of shapewear to the male market.

Men’s shapewear is nothing new. Ancients Greeks wore a form of girdle as far back as 750 BC. Today brands like Colombia’s Leonisa produce a men’s shapewear range, Leo, which includes compression tank tops and padded butt enhancer briefs. The difference between men and women, however, is that men are unlikely to admit they wear shaping garments.

Kim K’s pants may change that. The brand’s launch campaign starred Brazilian footballer Neymar Jr, basketball star Shai Gilgeous-Alexander and NFL hotshot Nick Bosa. The range consists of three collections: Cotton, Stretch and Sport. The focus of the range is activewear, rather than body contouring, which sets it aside from the women’s offering and will likely appeal to a wider male audience.

And while Skims underpants shape subtly, other designers have gone all out.

Actor Nick Kamen stripped off in a TV ad for Levi's in 1985
Actor Nick Kamen stripped off in a TV ad for Levi's in 1985

“Recently you have new companies that have introduced designs that separate and support the different elements of the male anatomy to keep it all in place for practicality and comfort,” says Hems.

This is all new to me. My underwear journey has been unremarkable apart from a short spell in my early twenties when I worked as an advertising copywriter for Ann Summers and briefly flirted with an elephant-shaped posing pouch. For my generation (I’m 54) you were a Y-front brief wearer, just like your dad and his father before him.

It all changed for me in 1985 when model Nick Kamen stripped to his white boxers in a launderette for the iconic Levi 501s advert. After that it was boxers all the way until the early nineties when Calvin Klein introduced the boxer brief, a revolutionary hybrid combining the stretchy snugness of the brief with the shape of the boxer. The first set of ads for these gamechangers featured a ripped Mark Wahlberg. The innovation of a branded waistband allowed me and my peers to peacock in bars and nightclubs, pants hiked up, trousers pulled down, signalling to anyone who was interested that we were packing a pair of expensive designer underpants.

Fast forward to 2023 and I had become underwear lazy, nuzzling my junk in the familiar, uninterested in experimenting, until Kim came along and revived my interest in undies.

Nick’s adventures in undies

'Strong care home vibes': M&S pure cotton high-waisted briefs
'Strong care home vibes': M&S pure cotton high-waisted briefs - Andrew Crowley

M&S pure cotton high-waisted briefs

£20 for 3 pairs

In hindsight, possibly not the best style to try first when looking to rekindle a love for lad’s lingerie. As soon as I hiked these bad boys up, I felt like I was waiting to be changed. They gave strong care home vibes. My wife Stephanie, a decade my junior, walked into the bedroom and, faced with a frightening vision of her future, walked straight out again. Passion killers maybe, but according to Hems, they do have a place.

“It is always worth considering where your waistband is. A higher waistband is better for men with bigger posteriors or taller men. They also help prevent builder’s bum as they don’t tend to ride down if you bend or get pulled down by a belt,” he says.

'No-frills': M&S pure cotton briefs
'No-frills': M&S pure cotton briefs - Andrew Crowley

M&S pure cotton briefs

£18 for 5 pairs

These are the underwear versions of a Ford Transit van. No-frills, trusty and versatile enough to carry a variety of loads. Wearing them was nostalgic, like being acquainted with an old friend. I was also surprised to find they didn’t look too bad with my physique. The elastic around the high legs took a bit of getting used to but overall they were comfortable and practical. One criticism. The Y, which is supposed to provide easy access when nature calls, was designed in such a way that in field tests I found myself fumbling deep in the folds of material between my legs trying to find a route out.

'They feel premium': Skims stretch boxer briefs
'They feel premium': Skims stretch boxer briefs - Andrew Crowley

Skims stretch boxer briefs

£24 for one pair

Light and soft but also robust, they bear up well to activity. Made from 91 per cent modal and 9 per cent elastane, they have an engineered pouch and gusset structure that holds everything in situ, which works on a practical level for exercise and also creates some aesthetic confidence, because it creates a display case for the crown jewels. Stephanie acted unimpressed, but I sensed a faraway look in her eye that I hadn’t seen for some time. All in all, these are a silky claxon-call for the genitals. They feel premium, push everything out front and announce it loudly.

'These were my favourite': Lululemon Always in Motion mesh boxers
'These were my favourite': Lululemon Always in Motion mesh boxers - Andrew Crowley

Lululemon Always in Motion mesh boxers

£88 for 3 pairs

More expensive per pair than Skims, but it tells. Technically not boxers, but boxer briefs, these were my favourite. They got Stephanie’s vote too. They were softer than Skims and made from 86 per cent modal, 9 per cent Lycra elastane and 5 per cent polyester. The ergonomic pouch provided room and support and held everything in place without making a fuss of it. While the Skims grabbed my bits, these gently cupped and protected them while I smashed out a 45-minute HIIT class. Comfort, support, practicality, but also stylish. And they come in a range of brighter colours at a lower price, which Hems explains can help boost confidence.

“Men tend to buy underwear for practical reasons and overlook the benefits of choosing the right colour. When you find a colour that works with your skin tone it brings out the best of you,” he says.

'Quintessentially gentlemanly': Hamilton & Hare striped cotton boxers
'Quintessentially gentlemanly': Hamilton & Hare striped cotton boxers - Andrew Crowley

Hamilton & Hare striped cotton boxers

£40 for one pair

Having fallen out of love with boxers, it was a revelation to slip on a pair of these and thrill at the liberating effect of ventilation. Made from 100 per cent cotton these were designed by a Savile Row tailor and, according to the brand blurb, had a triple stitched fly and a “natural corozo nut button”, whatever that is. They looked stylish, fitted well and were quintessentially gentlemanly. I loved them until I pulled on a pair of slim fit jeans, and they ruched up like a pair of baby’s swim pants.

'They gave the missus the ick': Rubinacci silk satin boxers
'They gave the missus the ick': Rubinacci silk satin boxers - Andrew Crowley

Rubinacci silk satin boxers

£130 for one pair from Mr Porter

According to the blurb, these 100 per cent silk Italian boxers with mother of pearl buttons are “designed to make you feel as good as you look”. They made me feel like inviting a model to my hotel room. Designed for show, and perhaps for guests at a rather dodgy party, they reminded me of some of the VHS tapes my dad kept hidden in the cupboard when I was a kid in the Eighties. Maybe things would have been different if I had a hairy chest and a medallion? They gave the missus the ick too. Best kept for attention-seeking oligarchs.