not have a penny to bless yourself with

not have a penny to bless (oneself) with

old-fashioned To be extremely poor; to have very little or no money to spend. When I stepped off the boat, I didn't have a penny to bless myself with, but I knew the future was bright. They used to be so well off, but the economy crashed and their business closed, and they don't have a penny to bless themselves with anymore.
See also: bless, have, not, penny
Farlex Dictionary of Idioms.

not have a penny to bless yourself with

be completely impoverished. dated
This expression refers either to the cross on the silver pennies which circulated in England before the reign of Charles II or to the practice of crossing a person's palm with silver for luck.
See also: bless, have, not, penny
Farlex Partner Idioms Dictionary
See also:
  • fashion
  • rain pitchforks
  • an old fogey/fogy
  • a whole team and the dog under the wagon
  • a pile Jack Rice couldn't jump over
  • a roll Jack Rice couldn't jump over
  • ravished with delight
  • (butter and) egg money
  • a stuffed shirt