I work in a job where what you wear matters and gets noticed. I haven't bought a new shirt, dress pants, or new suitcoat in 5 years. I
have bought a lot of used ones. It is actually fun. I can't tell you how many times I've gotten compliments and then they ask where I get my clothes. When you tell them "St. Vincent de Paul", it is fun to watch.
Go looking for a religous thrift store (Goodwill is actually for profit) in an expensive neighborhood. I go to the St. Vincent de Paul store down the street. Every lawyer in town dumps their clothes there for a tax writeoff. Last trip I picked up two pairs of dress slacks, wool and wool/silk. Perfectly clean and I paid a whopping $2.50 each. Easily $125 pants selling for $2.50. Bought a wool sportscoat for $5. I bought a Brooks Brothers suit for $10. I felt like I was robbing a bank. Trust me, these are not ragged out clothes.
December is the time to go. Folks want the deduction before the new tax year.
One more thing: do I feel guilty about buying clothes that are better sold to the poor? No, because the working poor don't normally buy sportscoats. They are mostly wanting work clothes and the other stuff goes unsold. I know this because I felt guilty and asked. Like I said, if you find the right place, you'll feel like you are robbing a bank. But you aren't, and the money goes to charity. How can you lose?
