Do you have a written clothing policy? If not, I highly recommend it. Having policies written down gives you something to fall back on, and for parents to refer to so they know what you expect. Also, when you get a situation like this, you can 'refresh" the parent's memory about what you expect. Personally, I wouldn't care about the sleeper, because I require shoes (or at least slippers) for children who are walking. And I require proper outerwear, too. I have it written down so I can enforce it. When this parent hands you the half naked child outside does she also give you the coat, shoes, mitts and hat for her? If not, wouldn't that be considered neglect? My advice is, ASAP, write down what you expect of all parents in terms of clothing, inside and out, and refuse service if this is not adhered to. You don't have to terminate, just send her home to get the appropriate clothing.