Just because you're stepping out with a date doesn't mean a dress has to be cocktail-ready. Cressida's T-shirt style will be comfortable at dinner or sitting at the movies, but is still just a touch sexy. And sneakers? So in right now.
Her basic mix of miniskirt and tee is simple, but don't discount it—guys are forever telling us how much they love girls in T-shirts. Brighten it up like Cressie too by picking varying shades of a bright color.
For an evening out when the weather forecast looks chilly, layer like crazy. Where you might pull on a trusty puffer jacket or fleece zip-up to run errands on the weekend, leave it at home for date night and pull a tailored blazer over a sweater instead.
Is your personal style closer to Kate's or Cressida's?