I was recently having some real issues with being comfortable but stylish during my down time. I have my work wardrobe under control. And I have some cheapo workout clothes from Target that seem to do the trick (although I would love to upgrade), and I have even found pajamas that are cute and comfortable (thank you Garnet Hill). But on the weekends, I really struggle with clothes that I can run errands in and maybe even leave on while I'm hanging out with the fam.
But I finally came up with a solution, and it involves an overall change in my philosophy of clothes. This philosophy consisted of wearing pants almost all of the time. For some reason I decided that pants, jeans or capris (almost never shorts, oh the horror!) were comfortable and dresses and skirts were not comfortable, but good for wearing to work or dressy occasions. But due to the fact that I can never find pants that fit exactly the way I want, I finally decided that this philosophy of dressing was completely delusional. So now I am all about the skirts.
Really, I don't know what took me so long. It is much easier to find skirts that fit. You don't have to worry about hemming a skirt so that it will go with one particular heel height, and you don't have to worry about a few pounds lost or (more likely) gained. One thing that helped spark this revelation was reading a blogger (sorry, I don't know wear) discuss her love of skirts. She stated that she can do anything in a skirt that she can in pants, except a cartwheel. Read Already Pretty's Pant Rant for some more skirt love.
So I have solved my what to wear on the weekend problem with knit skirts. I have two tiered knit skirts in both black and brown from Ann Taylor Loft that I got several seasons ago. And lucky for me, tiered skirts are still in style. I also bought this knit skirt by Velvet. It is sooo comfortable and sooo swingy. And if I want to step it up a notch on the weekends, like go to a restaurant that involves being served by a waitress (it does happen occasionally), I can switch to a knit dress (I know, I'm living on the edge) or a more structured skirt.
Moral of the Story: Skirts=Comfy Duds