What lies beneath matters, so choose your underwear carefully chaps

In 1933, the journal Men’s Wear announced that a pair of pants should bestow on their wearer ‘the grace of Apollo, the romance of Byron, the distinction of Lord Chesterfield and the ease, coolness and comfort of Mahatma Gandhi’.

If only it were so simple. When I started researching this piece, I quickly realised that the business of picking the right underthings is fraught with difficulty. The first man I spoke to admitted he once ripped his clean in two when striding down Pall Mall, being possessed of what his tailor refers to as an ‘athletic seat’. The second, newly divorced, turned down the offer of a nightcap from a very attractive woman a few weeks ago ‘because he was worried his pants wouldn’t pass muster.

Clearly, the nation is in the grip of what Jeremy Paxman referred to as ‘widespread gusset anxiety’ in the famous email he sent to Marks & Spencer complaining about its merchandise. The good news is that it isn’t actually difficult to get it right, but first, a bit of backstory a brief history, if you will.

Underpants as we know them came into being in the 1920s. Before that, gentlemen mostly went about in flannel drawers, or, all-in-ones known as ‘union suits’ with buttons up the front and button-up access flaps at the back. Then, in 1925, the founder of the boxing-equipment company Everlast started fitting stretchy waistbands to the shorts worn by prize-fighters. Within 20 years, his invention had gone mainstream, thanks in part to how nicely these ‘boxer’ shorts complemented a well- cut pair of trousers.

To business. Boxers or briefs? Well, if you’re under 40 and can still touch your toes, stretchy smalls are fine and flattering but, at the first sign of middle-aged spread, you need to swap them for plain old cotton. A Bunterish silhouette is not enhanced by Calvin Kleins. If you go down the boxers route, pastels are the smart choice: think cornflower blue, pistachio or salmon pink. Tartan is fine, if a bit of a 1980s throwback, and red always raises a smile. Pick dark green and you run the risk of looking like a snooker table when you bend over.

Avoid novelty fabrics at all costs. ‘I once impulse-bought a pair of silk boxer shorts during a press trip to Hong Kong,’ confesses one of Fleet Street’s most respected commentators. ‘They itched like anything and, frankly, I looked ridiculous. My wife would never have stopped laughing. I ended up leaving them behind in the hotel.’

Now that’s settled, consider your socks. They might look perfectly all right to you, but how will they fare when you sit down and cross your legs? Too many otherwise dapper chaps find themselves falling victim to the Sock Gap. This isn’t the brief window of opportunity in which you can whip them off when disrobing (miss it, and you’re a naked man in socks), but the flash of calf you risk giving the room if they’re too short and your trousers ride up.

Knee-high socks are the best defence against this, but don’t discount the old- school alternative. A female friend gets all misty eyed when she remembers running a hand up a paramour’s leg and feeling, through his tweedy trousers, the unmistakeable outline of a pair of sock-suspenders.

Vests have developed a bad reputation over the years: a bit Kwik-Fit, a bit Readers’ Wives. However, thick cotton singlets are very Old Hollywood, especially if accessorised with Scotch and a furrowed brow. But if you’re going to wear one, it needs to be whiter than white shades of grey have no place in your underwear drawer.

Finally, a word about braces. Worn properly, they can be tooth-grindingly sexy – that fishtail bit at the back of your trousers they button onto is purest Flashman. Not all of them are created equal, however. You want them to be at least an inch wide (yes, size does matter), felt for daytime and white moiré for evening, following James Bond’s lead. Resist patterns you are not in a 1970s ska band.

Ultimately, when you stand in front of someone in your underwear, whether that person is your wife of 15 years’ standing or an attractive divorcée you met 15 minutes earlier on the bus, you’re saying to them ‘This is the real me’, so you need to put some thought into what you’re putting on—or leaving off, as the case may be.

Halfway through writing this piece I had lunch with an almost pathologically neat and precise colleague, the sort of man who irons his handkerchiefs. In the spirit of journalistic enquiry, I decided to ask him what sort of pants he wore, fully expecting him to start blushing furiously or even storm out.

‘Oh, I don’t,’ was his breezy reply. ‘Never have.’ I choked on my panini. ‘One less thing to worry about in the mornings,’ he continued, buttering his bread roll. ‘And between you and me, I’ve always found them a bit restrictive.’ Proof, if any were needed, that you should never judge a bloke by his cover.

** This article is taken from our GENTLEMAN’S LIFE magazine, out this week with COUNTRY LIFE. Read the 39 steps to being a gentleman.