[Always *]

I agree with Robin, why do you need to spend all your money on an outfit? Why don't you just go to a thrift shop or something, you can always get really good stuff there, you'd be surprised OR you could always wear what you have already and borrow clothes (I lend clothes to my friends sometimes).
That being said all I hear is you making excuses about how there is literally no way for you to make money. Example, just cause it is hot doesn't mean dogs don't want to be walked. Do you know how beserk some dogs would go if you kept themout how there is literally no way for you to make money. There are A LOT of really easy kids to babysit. You could just insist on only children and/or toddlers or babies. Having only one child to contend with AND if the child is 18 months old or 2 years old tend to be easiest.