Otonari no Oneesan ni Arekore sareru - Vol. 3 Ch. 67 - Destitute

[MangaDex]

 

[SquigglesJP]

Wait... hang on... destitute? cambridge says it means "without money, food, a home, or possessions"... it doesn't says he doesn't have them milkers though or am I not understanding something here?

 

[xanon]

I don't think you qualify for that deal, Chie-chan.

 

[Kaarme]

Browsing many a chapter backwards, Kento did call her onee-chan (or something close enough), back when he was very young. Naive illusions are already long gone, but at least love remains.

 

[Landale]

Wait... hang on... destitute? cambridge says it means "without money, food, a home, or possessions"... it doesn't says he doesn't have them milkers though or am I not understanding something here?

More generally, it means lacking something desired or of importance. Basically the shirt is once again saying she lacks tits in a fancy way.

 

[FloorRoof]

Wait... hang on... destitute? cambridge says it means "without money, food, a home, or possessions"... it doesn't says he doesn't have them milkers though or am I not understanding something here?

When you fish out your vocabulary straight out of a thesaurus, like the author likely does, you eventually wander into semantically distant terminology, because the meanings of synonyms don't overlap perfectly.
For instance, 'poor' is a synonym of 'small' and can replace it in some contexts, while 'destitute' is a synonym of 'poor' that cannot work as a synonym of 'small' at all (it might in other languages like mine, though).