A.S.
For work clothes, check out Bottomless Closet. I don't know all of the specifics about the organization, but they help women (primarily low-income, I believe) with interview skills and maybe some job training. They have a store for women to shop for work and professional clothing among donated items. Check their website because, unlike Goodwill or Salvation Army, drop-off is a designated day per month. I donated a lot of stuff one time this summer. They're located downtown on LaSalle, and I was a little worried about parking, but it was the easiest experience. Since it was a Saturday morning, there's little traffic. As soon as you pull up, there's a team of people to help unload your car and give you a tax donation receipt. I think they'll accept men's clothes, too.
As for the kids stuff, I donate those items to Salvation Army. As someone pointed out, they sell the items at a low price so that it's affordable for people who can't buy new clothes for their kids. They then use the proceeds for their own work in helping homeless and hungry people in Chicago.
