I really like this look with the shirt underneath and the boots. I would wear this to work or pair it with some black tights and a patent leather shoe. Chloe button neck dress at net-a-porter.I think that this would be a cute date outfit paired with some colorful tights. Sixties spot print dress available at asos.
Valentine yoke collar dress at la garconne.
Make sure that your shift dress is not too long, you don't want it to look matronly.