While this is heavily species dependent, assuming a highly diverse set of species, I'd imagine at least a part of the cultural evolution would be clothes as a tool for courtship, not necessarily protection. Covering up the naughty bits, showing off status through fashion, hell even basic clothing for specific jobs (however minimal they may be) are likely occurrences in such a setting.
And to piggy back off the multi species tangent; I'd imagine the less fur you have (or fat) the more likely you would be to wear clothes for comfort or protection.
The size problem is simply resolved less through diversifying the clothes, but modularization. Foxes don't wear pants, they wear togas. Lizards wear leather straps around their girdles, birds might only ever had a bandolier and a hat. You don't buy a shirt, you buy a strip of cloth with sleeves. Then you tie it around you and secure it with a clip.
The diversity surrounding species variety would motivate eclectic industries capable of handling multiple different forms and needs. A niche, unless highly ludicrous, would be doomed financially.
EDIT: Negating courtship is also a reason for clothes such as in a business
While this is heavily species dependent, assuming a highly diverse set of species, I'd imagine at least a part of the cultural evolution would be clothes as a tool for courtship, not necessarily protection. Covering up the naughty bits, showing off status through fashion, hell even basic clothing for specific jobs (however minimal they may be) are likely occurrences in such a setting.
And to piggy back off the multi species tangent; I'd imagine the less fur you have (or fat) the more likely you would be to wear clothes for comfort or protection. The size problem is simply resolved less through diversifying the clothes, but modularization. Foxes don't wear pants, they wear togas. Lizards wear leather straps around their girdles, birds might only ever had a bandolier and a hat. You don't buy a shirt, you buy a strip of cloth with sleeves. Then you tie it around you and secure it with a clip.
The diversity surrounding species variety would motivate eclectic industries capable of handling multiple different forms and needs. A niche, unless highly ludicrous, would be doomed financially.
EDIT: Negating courtship is also a reason for clothes such as in a business