Underwear Considered

The Postbag: How I Converted My Mates

Six letters on talking friends into briefs: a wager that went far too well, a five a side team, a wedding crisis and a son who got there first.

· · 12 min read

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The Postbag is where readers write in and the editor writes back. The correspondents are, let us say, composites. The situations are not.

We asked, in a small line at the bottom of a piece about persuasion, whether anybody had actually managed it. The answer arrived in a volume requiring a second table in the office and a firm word with the person who suggested it.

The mail splits into two piles. In the first are men who converted somebody and now find the convert has gone past them at speed and is out ahead making the case in ways they would never have dared. In the second are men who have been at it for years with nothing to show for it, and who write in with the calm of a fisherman who has caught nothing since March and intends to go out again on Saturday.

We have printed both, plus one letter that reverses the arrangement entirely. None of the methods below are endorsed by this magazine, several are covered as things to avoid in How to Convert Your Friends to Briefs Without Losing Them, and at no point did we suggest wagering money on it.

The wager I won, and have regretted daily since

Sir,

In November I made a bet with Douglas, whom I have known since we were put in the same under fifteens squad, neither of us any good. The terms were simple. He maintained he could not wear a brief for a calendar month. I maintained he could. A modest sum was staked, in front of witnesses, and I considered the matter a formality.

He completed the month. He then completed a second month without being asked. By February he had done what I can only describe as reading, and by March he was correcting me.

At a dinner in April he explained leg opening construction to my wife, who has never expressed an interest, while I sat opposite holding a serving spoon and saying nothing, because everything he said was correct and I had taught him it. He has views on waistbands now. He has a view on my waistbands. Last month he told a man in a car park that the whole thing came down to fit, in exactly my cadence, and the man agreed with him.

I won the bet. I have not felt like a winner since the second week of January.

Gerald Pinnock, Shrewsbury

The editor writes: Every movement produces somebody more devout than its founder, and the founder is never ready for it. This is not ingratitude, it is the ordinary arc of the recent convert, who has none of your years of quiet embarrassment to slow him down and is operating at full power with no dimmer switch. It burns off. Give it a year.

Take the consolation that a man repeating your cadence in a car park was listening more closely than you ever knew.

The wager is the one method we advise against, since it makes the garment a matter of winning rather than comfort, and a man proved wrong in front of witnesses usually digs in. That he did not is luck. What he might have said instead is at Things Men Say About Briefs, Ranked by How Wrong They Are.

The season it went round the team

Dear sir, I am not going to pretend there was a plan, because there was not, it started in September when Baz did his groin and asked me in the car what I wore for football and I told him plainly, without any of the carry on, and he tried it and said nothing for six weeks which I took as a bad sign until he mentioned in the pub that he had bought two more, and after that it was Chris, who asked Baz and not me, then Owen, who asked nobody and simply appeared in the changing room in October wearing them as though he always had, daring anybody with his eyes to say a word, which nobody did, and then over the winter it went round the rest of them the way a cold goes round a primary school, one a fortnight, always quietly, always after somebody had pulled something, until by the last game there were nine of us and only Mattie holding out, and Mattie only holds out because his brother started it and he will not give his brother the satisfaction, which I respect, and which I expect to outlast us all.

Dermot Slattery, Athlone

The editor writes: This is the only method that reliably works and almost nobody has the patience for it. You answered a direct question, once, in a car, and then shut up for a season. The rest was Baz saying nothing for six weeks and then buying two more, which is worth more than any speech.

Note that they all converted after an injury or a niggle. A man who has just pulled something is briefly willing to reconsider his kit, and that window is the subject of Right Support, Right Sport: What to Wear for What You Do. If Mattie ever cracks, a plain sports brief is the thing to have in the bag, handed over without ceremony.

Do not mention the nine to him. He will be counting.

An emergency in room 214

Dear editor,

My brother in law has been dismissive of the subject for eleven years, largely because it annoys me, which is a legitimate hobby and I have never begrudged it.

At my niece's wedding in June he came to my door at approximately one fifteen in the morning with a problem he described as private and structural. His own arrangements had failed him across a long day of standing, dancing and one ill advised attempt at a lift during the ceilidh. There had been chafing. There was still chafing. He had photographs at ten the following morning and the trousers were not negotiable.

I had a spare pair. I have always had a spare pair. I handed it over in the corridor without commentary, because I had waited eleven years for that moment and was determined not to spoil it by speaking.

He wore them for the photographs. He wore them home. In August he mentioned, apropos of nothing, that he had bought some, then changed the subject at such speed that a bird flew off the fence.

Wilf Anstruther, Perth

The editor writes: Not speaking in the corridor was the finest thing you have ever done. One sentence at that moment, any sentence, and he would have been back in his own kit by Tuesday out of pure principle.

A wedding is the highest pressure day most men ever ask of their clothing, and almost nobody prepares for it, which is why we wrote Under the Suit: What to Wear on Your Wedding Day. Twelve hours upright, warm rooms and dancing will find any weakness in what you have on.

We file your corridor as further evidence for The Emergency Pair: A Tribute. The man who keeps a spare is not fussy. He is running a service for everybody else in the building.

Field report, month twenty six

To the desk,

Subject remains Alan, of accounts payable, who sits four metres from me and has done since 2024.

Position at last report: dug in, well supplied, hostile to the topic. Position now: materially softened.

Month nine, subject volunteered that his current arrangements "ride up on the train". No action taken by me. Month fourteen, subject asked what I meant by "stays put", question answered in one sentence and not revisited. Month nineteen, subject went to Portugal and returned having independently discovered that the men there are not embarrassed about any of this, a fact he reported to me as news. Month twenty two, subject bought one pair. One. He did not tell me. I learned it from Priya, who learned it from him at the printer.

Month twenty six, this week, subject said out loud, to the room, that he could not go back.

I have not celebrated. I have not mentioned it. The correct response is to hold the line and say nothing for another quarter, and I intend to.

T. J. Hardcastle, Warrington, writing from the desk by the window

The editor writes: Twenty six months is not slow. It is how long these things take when done properly, and your discipline in month fourteen, answering the question once and then leaving it alone, is the part most men cannot manage.

The Portugal trip did more work than you did, and that is worth accepting with good grace. A week somewhere the garment is unremarkable undoes years of quiet self consciousness in a way no colleague can.

Your instinct to say nothing is right. If you want one more useful move, put a single merino brief in the office secret santa pool and let him pick it out of a hat, and if he asks how long the strange stage lasts, Making the Switch: The 14-Day Brief Plan answers it without either of you having to.

A record of nil returns

Dear sir,

Thirty one years teaching physical education, eleven of them as head of department, and I have converted nobody.

Not one. Not a colleague, not a friend, not my brother, not either of my sons in law, not the four men I have played bowls with every Wednesday since I retired. I have raised it perhaps a dozen times in total, always briefly, always when asked, and every one of them heard me out politely and carried on precisely as before.

I am not writing in a spirit of complaint. Your correspondents seem to be doing rather well and I felt the record should show the other column. I have been comfortable for four decades. I have never had to adjust anything in a car park, and I have watched a great many men do exactly that while explaining to me that what I wear is old fashioned.

Bernard, who is seventy nine and has the best serve of the four of us, told me last week that he had thought about it. That is the sum total of my life's work in this area, and I found it more satisfying than I expected.

Ken Rutherford, Barnsley

The editor writes: Thirty one years and one Bernard is a better return than most campaigns and a far better one than shouting. You have done the thing the loud ones never manage, which is to be visibly, boringly fine for four decades in front of men who noticed more than they let on.

We push back on one word. Nil is not the figure. You cannot know what any of them did privately a fortnight later, and the ones who go quiet are usually the ones who went home and thought about it.

Several may also simply prefer what they have, and that is allowed. There are conditions under which the loose boxer is the best garment in the house, as we set out in In Praise of the Loose Boxer.

Tell Bernard the serve is holding up.

The boy got there first, which I did not enjoy

Dear editor,

I am fifty four and my son is nineteen, and I want it on record that the sequence of events was not my doing.

He came back from a summer in Spain having reorganised several things about himself, most of which I said nothing about. Some weeks later he was putting a wash on and made a remark, entirely without edge, about the state of what I had contributed to the machine. He then said, and I quote, that the reason mine all look like that is that I have been buying them five at a time since before he was born and have never once liked all five.

I told him he was being ridiculous. I then went upstairs and counted, and he was right, and I sat on the end of the bed for a while.

I bought two pairs, on my own, telling nobody. I have now bought rather more than two pairs. He has never mentioned it again, which I suspect is deliberate and which I find slightly unnerving, as though he has read something I have not.

Marek Dunphy, Cork

The editor writes: He has read something you have not, and the something is you. Nineteen year olds are very good at spotting a decision a parent made once and then stopped examining, which is why it stings and why it is nearly always correct.

Sitting on the end of the bed after counting is a specific experience and you are not alone in it. We wrote a whole piece from inside it at A Letter to My Nineteen Year Old Self, Who Wore Boxers.

His not mentioning it again is the most impressive part of your letter. Most people, at any age, cannot resist the follow up.

Buy one good cotton rib brief, wear it a fortnight, and if it still pleases you after the washes, buy more of exactly that. The rule works at nineteen and at fifty four, and it is the only thing here your son has not worked out for himself.

The editor's postscript

A conversion is only ever half the story. The other half happens in the room where the newly converted man has to get changed in front of the people he used to agree with, and that correspondence is filed under The Postbag: Dispatches from the Locker Room. For the harder case, the household that has opinions about what arrives in the wash, see The Postbag: The Home Front.

Questions people ask

How do I switch from boxers to briefs?

Buy one pair rather than a multipack, in the correct waist measurement rather than the letter size you have always used, and wear it for a normal working day. Judge it on how it behaves after eight hours of sitting, walking and getting in and out of a car, not on the first ten minutes. If it rides up, digs in or rolls at the leg, that is a fit fault and you need a different pair. Keep your boxers for the sofa and hot nights.

How long does it take to get used to wearing briefs?

About two weeks of consistent wear for most men. The first two or three days feel unfamiliar because the sensation of support is new, not because anything is wrong, and the usual mistake is deciding after one day. By the end of a fortnight the novelty has gone and you can judge the garment on its merits. If discomfort remains at that point, it is almost always a sizing or construction problem rather than acclimatisation, and a different cut solves it.

How many pairs of briefs should I buy when starting out?

One or two. Buying a large quantity before you know how a cut suits you is how drawers fill up with things nobody wears. Wear the first pair through several washes, check that it holds its shape and that the waistband has not loosened, and only then buy more of that exact model. A settled rotation for most men is around ten to fourteen pairs, which covers a normal laundry cycle without reaching the back of the drawer.

What size briefs should I buy if I usually wear boxer shorts?

Measure your waist with a tape where the waistband will actually sit, which is lower than a tailor measures for trousers, then read the maker's size chart rather than assuming the letter you wear in boxers carries over. It often does not. Loose boxers are forgiving of a wrong size, so many men have worn the wrong letter for years without noticing. Continental sizing runs differently again, so check the chart with any unfamiliar brand.