Oh yes an excuse to talk about frogs some moreYeah, clothing is a problem when it comes to animal people. Can share some insights from my ponderings.
I guess the first question is, do they even need clothes, and what you've already touched upon, can they make them without overt difficulty to satisfy the need. In my setting the frog people generally, don't wear clothes, it's mostly a ceremonial deal for the priestly class or other authorities. The most covered up occupation is a leper doctor, for obvious reasons
They don't feel the same shame as we do, and they don't settle in areas where they would freeze. I picture them being a lil' bit more reptilian-ish than a pure amphibian, with somewhat sturdier skin that prevents them from drying up, that is, they drink as we do and wouldn't die in salt water, though it does cause irritation to some races. With the cold-blooded aspect, that I haven't defined much as of yet, but it is clear to me they should be susceptible to cold, which presents a problem for kvaksas from the Great Island, where there's a seasonal climate and they have to deal with winter, even snow. It wouldn't be very smart of them going full on dormant, sealing within their clay-coated insulated homes and not doing anything for a whole season. For anyone operating outside, clothing is a must have.
There are these fur bags the kvaksas rest in in winter, but they would have their uses outside, too, I imagine it being strapped to a back of a hound so the rider is warm, this would let hunters go out in the winter. The pack monitors lizards would be dormant, though, so each settlement would have to fend mostly for itself - winters would cut trading completely in these parts.
For the question how these are made, the frogs do possess some fine motor skills, males having an enlarged thumb excellent for weapon gripping, but there's also magic, all of the weaving was done by magi-priests at one point, before looms were designed, who invoke a "civilization" spell upon the raw plant material. I haven't considered leather much until I've started thinking about the winters, but it is clearly the more accessible resource compared to cloth, the production would be easier, and the demand for leather straps is high. I guess magic could be an answer for clothes of your dragon people, but that can prove quite difficult to handle and define well.
On the helping to put clothes on problem, might not be a problem, maybe it's just a
bruh moment social thing. Kvaksa warriors strap their weapons to their backs, and this also has to be done with help of a fellow, but outside combat it's just much more effective to have both hands free, so no one thinks about it too much. It all really depends on what role does the clothing have, is it covering, cold, status, ritual, pure aesthetic? There's a lot of think about, and I'm sure you can come up with something interesting.
But I made real life test for you
All hail the almighty sock dragon