For me, and judging from the responses to the "pushing the envelope" thread, for many others, casual dressing is the most difficult to master. Why is it so hard for us?

I think it is so hard because we require much more from the casual outfit than from a work outfit (be it a business one, business casual, or a smart casual). For me, casual when I am just running errands by myself, is not so difficult. It gets difficult when I am with the kids. When I am with the kids (which is most of the time when I am wearing casual), I need my outfit to be:
1) reasonably stain-proof and low-maintenance - wash-and-throw-in-the-dryer type (that is, not white so that the stains don't show so much, and also made of a very sturdy fabric, to withstand washing when the stains do occur),
2) very comfortable and modest enough to climb the jungle gym to rescue the youngest kid (that is, no skirts),
3) go with flats - city sneakers or such (see the jungle gym item),
4) not require constant rearranging and with nothing that can be caught in the playground equipment (again, the jungle gym item), which means, in particular, no scarfs, no lower necklines, no dangling jewelry,
5) go with a cross-body bag (again, see the jungle gym item - a cross-body bag is a must),
6) and, on top of that, to look nice!
I am starting to think this is an impossible task.

What do you say? What requirements do you have from your casual outfits? Those of you who are doing well with their casual outfits, can you share your tips, tricks, and photos?

And, just for fun, here is an outfit I ended up wearing for my birthday outing with my husband: http://picasaweb.google.com/lh.....directlink
Remember, I thought we will go out for a nice dinner and planned to wear my ruffled black ATL dress (the one Shiny has as well)? Well, my sweetest husband surprised me with a private sailing lesson on a yacht! I am wearing DKNY Soho jeans, city sneakers, sleeveless blue-and-white patterned top, pearls, and a red-and-white patterned bandana (ahem ... can I call it "pattern-mixing"?). It was amazing fun!