Number them
Matching sibling shirts work when the design admits there's an order. One print, one big numeral each — it's funnier than a coordinated set and it survives a fourth arrival.

Sibling sets usually try to be sweet about it: coordinated colours, a bear and a smaller bear, big sis and lil bro.
The version that gets worn admits what's actually going on. There's an order, everybody knows it, and the joke is that it's printed on them.
Why numbers instead of roles?
Because roles change and numbers don't.
Big sister stops being funny when a third arrives and she's now the middle one. Number 1 survives every subsequent arrival, and the new person simply gets a 4.
There's also the thing numbers do that words can't: they're legible to everyone and meaningful to almost nobody. A stranger sees three kids in matching shirts with digits. The family sees the entire pecking order.
Does it work for adults?
It's arguably better for adults, and nobody makes it for them.
Three siblings in their thirties in matching numbered shirts at a family gathering is a considerably funnier object than the toddler version, and it's the case the market ignores entirely — sibling merchandise assumes everyone involved is under six.
A set made for grown siblings at a reunion, a parent's birthday, or a funeral works for the same reason the numbers do: it acknowledges the hierarchy without anybody having to discuss it.
What should the print register be?
Loud. This is not a design that wants to be tasteful.
The version above is bootleg cartoon lettering — fat outlined letters, a drop shadow, an airbrushed fill. It's the register of a joke, and the joke is the point. A delicate line drawing of three birds would be the same idea rendered as a lifestyle product, which is a different and much quieter object.
Loud also survives the actual use: these get worn by people being photographed together, and a small mark disappears in a group shot.
Should the shirts match exactly?
The print should. The garment colour is a real choice.
Identical shirts read as a set for a photograph. Different colours with the same print read as a set rather than a uniform, and people wear those more afterwards.
For a one-day thing — a birthday, a reunion photo — matching is fine and looks better in the picture. For something anyone will wear again, let them pick.
What about the numbers themselves?
Big, and assigned by birth order without negotiation.
The temptation is to soften it — to give everyone a 1, or to use initials instead. That removes the entire joke. The design works precisely because it's a ranking that nobody chose and everyone accepts.
The one variation worth knowing: twins both get the same number, which is funnier than either alternative and has its own set anyway.
Can I add one later?
Yes, and that's the practical advantage over buying a set.
There's no minimum, so shirt number four gets ordered when number four exists — same design, same print, new digit. The set grows rather than being replaced, and the earlier ones don't become wrong.
That was impossible when a matching set meant a bulk order in guessed sizes.
Is there a version for one sibling?
The strongest one, and it's a gift rather than a set.
A single shirt with just their number, given by the sibling who is a different number, is a compact joke about a lifelong relationship. It needs no explanation to either person and completely mystifies everyone else — which is the shape most in-jokes want.
How do I get one made?
Describe it at JustOG — the word, how many siblings, and which number goes on which shirt. Pick a direction, drag the crop frame, see it composited on the real garment, and each one is made to order and shipped.
Designs other people have published are in the shop.
Nobody chose the order. Might as well print it.