I'm a lazy dresser. I used to really try to look cute, but that's when I had more money and when I was single. Lest you think I'm neglecting my husband, he has made it very clear he likes it when I look a little scruffy. In his ideal world, I would wear jeans, an oversized tee, and a baseball hat every day. To each his own.
The problem with this is that it's a slippery slope from this to pajamas all day. This winter, I've bought a few dresses on clearance and have happily discovered it is easier to wear a dress than it is to wear pants and a top. It's just piece and I don't have to worry about matching.
I've even managed to overcome the leg shaving problem that comes with wearing dresses: cable knit tights. I'm voluptuous and can't wear cable knit sweaters because they make me look chunky, but on my legs, they're fine. They're warm and you can get away with at least a week's worth of leg hair growth.
Shift and wrap dresses in jersey or ponte knit are the most comfortable. It honestly feels like I'm wearing a night gown. I am tempted by sweater dresses, but so far I haven't been brave enough to try one on yet. I'm worried it would cling in the wrong places.
I have this dress and love it. I'm thinking about getting it in another color. I have dresses similar to this and this. They are all very comfortable.
I still wear plenty of jeans and tees to keep my husband happy, but if I have to go out, I feel more pulled together and confident in a dress than I do in sweats and a ponytail.