So, not every dress works with a shirt underneath, but there are quite a few that do. For instance, a shorter dress works better. Adding the shirt can make the dress look quite conservative, therefore, a longer dress with a shirt can look too conservative.
I also find that thin-strapped dresses with a shirt don't usually work, whereas a dress with sleeves or even a strapless dress can work really well.
Due to the weather, I had a few more layers to add. Some leggings, a coat and flat boots. But go to your closet and experiment. Try your shirt on under different dresses or instead of leggings you could wear sheer stockings with some ankle boots. Try a few different versions and see what you come up with.
Coat: Mango - Shirt: Zara - Dress: Pull & Bear - Boots: Castelo - Ring: Parfois - Sunglasses: Ralph Lauren - Bracelet: Thomas Sabo - Watch: Calvin Klein
“For me, what I do is an artistic expression which is channeled through me. Fashion is just the medium.”
― Alexander McQueen