Thanks for all your replies, it seems like look #4 is the favourite, I don’t usually buy dresses for the winter season, so I thought I’d try this experiment.
Roberta, these lightweight dresses that you wear over jeans would be knee length or shorter and act more like a tunic top I’m guessing.
Suz, Lyn67, Jessikams, bella, yes, the fabric of the dress certainly plays an important role on whether this strategy works or not. A light weight fabric would feel confusing mixing it with heavy fabric items. This dress is a substantial cotton and the A line does helps the dress from clingy to the tights.
Angie, you guessed correctly, the taupe boots do indeed match my hair.
CarolS, yep, linen definitely wont work, and I get the idea of joyfully reuniting with your summer wardrobe after a long winter.
Jamie, more layers makes wearing this possible.
Helena, dark colours do help that’s for sure.
Sisi, yep wool will certainly be warmer than cotton.
Joy, Sorry your attempt didn’t work out, I guess not all dress styles would work doing this.
The Cat, I think I should be warm enough, I’ve got lots of layers going on.