My view on the latter has been expressed here before.
Theodore Dalrymple writes on this subject matter as well:
"people who claim it are inclined to demand of others that they take them at their own estimate
Perhaps I can illustrate the difference between self-esteem and self-respect in the seemingly superficial matter of mode of dress. In this matter I have changed my mind over the years: I used to believe in the virtues of slobbery, but I no longer do. This is because the slob is in effect saying to you, and to everyone else, I am not going to make an effort just for you. You must take me as I am, and not think the worse of me for that. Slobbery is not absent-minded, as when, for example, a learned professor, absorbed in the textual problems of Aeschylus or some such abstruse matter, puts on socks of different pairs. On the contrary, slobbery is militant. It demands simultaneously that you notice it and take no notice of it. It is self-esteem in the sartorial field. Note, however, that while the slob demands something of you, he demands nothing of himself. It takes no effort to be a slob: to be a slob is to indulge in unconditional self-regard."
Read the whole piece to understand his point.