Now, I'm all for this concept. I think it's a great way to get extra mileage out of your full wardrobe, and in most cases, it works.
Today I saw an example of it so not working. I wish I'd had my camera with me so I could post a picture of it all together to show you, but I'll just have to work with the pieces and see if you get the idea.
Most of the outfit was reasonably cute. It consisted of flat black Uggs (...poor black sheep...), a black and grey striped sweater, and black and grey pattern tights.
Here are some examples of the first three pieces:
Potentially a cute outfit, yes?
Well, this was the final piece:
Now, my disdain for the outfit may have come from the fact that the shorts were too short (and too ugly) to be acceptable in public regardless of the season. But then to try and "winterize" them made it all the more ridiculous and fashion-offensive to me.
What do you think? Are there some clothes that just shouldn't be winterized?