Ask six players for their size and you will get six confident answers, and one or two of them will be wrong. The guy who says large has worn a 2XL since 2019. The guy who says medium is thinking of a shirt he bought in college.
Nobody is lying to you. People remember the size they used to be and the size printed in a brand's cut that no longer exists, and they answer from memory because you asked a memory question.
Ask for a measurement, not a letter
The fix takes two minutes per person and it removes the guessing entirely.
Have each player take a shirt they already own and like the fit of, lay it flat on a bed, and measure straight across from armpit to armpit. That number, doubled, is the chest measurement. Then measure from the top of the shoulder straight down to the hem for the length.
Two numbers, from a shirt that is already the right size, on a person who is standing in their own bedroom. Compare those to the chart and the letter picks itself.
That is a better answer than a body measurement, because a chest measurement tells you about the person and a garment measurement tells you about the fit they already chose.
Send the actual chart
Put the size chart in the group message when you ask, not after somebody questions it. It costs you nothing and it makes the request specific enough to answer.
Every garment has its own chart. A tee, a long sleeve, a hoodie and a tank do not size the same, so a player taking a hoodie needs to check the hoodie chart rather than assuming their tee size carries over. It usually does. It does not always.
Unisex and women's cut are two different questions
Both exist and both come in the same design at the same tier price. The women's cut is its own chart with its own measurements, and it fits closer through the body.
Ask, and let people answer for themselves. Plenty of players prefer the unisex tee in a size down, plenty prefer the women's cut, and a captain guessing on somebody's behalf gets it wrong about half the time. One extra question in the group message settles it.
Sizing up, and the dryer
When somebody lands between two sizes, take the larger one. A shirt slightly too big reads as a shirt. A shirt slightly too small never gets worn, and the whole point of this exercise is six shirts at the table, not five shirts and a guy in his old polo.
Worth saying out loud to the team: cotton takes a little off in a hot dryer. The care instructions ask for a cold wash and a low tumble for a reason. The player who dries everything on high should take the larger size and will be happier for it.
Do it in the room, in one pass
Collect sizes the same night you collect money, on league night, walking around the table between matches.
Text threads lose sizes. Somebody answers in a different thread, somebody answers with a joke, and a size you got on a Thursday two weeks ago is a size you are going to ask for again. In person you get it once, you write it down while they are standing there, and it is done.
Six names, six sizes, one list. That list is the whole job.
When one still comes back wrong
Something will. The number to know is what fixing it costs, because that is what turns a disaster into an errand.
There is no minimum, so a wrong size is a one-shirt reorder. One tee is $27.99 with no new design fee, since the design was paid for the first time and stays on your team's page. Order the one shirt and move on.
The old fear here comes from bulk printing, where a wrong size means either eating it or ordering another run. That arithmetic does not apply when a single shirt is a normal order.
Ordering for the player who never answers
Every team has one. He was at the table when you asked, he said he would text you, and he has not.
Order a large or an extra large for him, based on what he is wearing every Tuesday, and tell him that is what you did. If it is wrong, it is a one-unit fix at the same price. That beats holding six people's shirts hostage to one guy's group chat habits for another two weeks.
Keep the list
Write the sizes somewhere that survives the session. You will need them again in four months, when two players have joined and everybody else wants the same shirt in a hoodie for the winter.
The captains who dread reordering are the ones who lost the list. The ones who kept it spend about four minutes on it.
The rest of the ordering, from the team name to money to reorders, is in the captain's guide to team shirts.