The short answer on Date Night Toos: pick one anchor piece, keep the palette to two colours, and let the shoes decide how formal the whole thing reads. A dress that fits the shoulders can be taken in anywhere else. One that does not, cannot. Lining is what stops a cheap fabric reading as cheap. Check where the waist seam sits on the model against your own proportions. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is shoulder fit, length and how the fabric moves. Everything else is preference. Two from the first group show the range: Rat & Boa's Selvina Dress at $275, and Significant Other's Shelby Dress at $216. The first is the considered buy; the second is the one to start with. Check where the waist seam sits on the model against your own proportions. A dress that fits the shoulders can be taken in anywhere else. One that does not, cannot. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

A belt turns a shapeless dress into a deliberate one. Let the dress be the loudest thing you own that day. From the second group, normakamali.com's CROSS BACK BIAS MINI DRESS ($125) is the one that earns its place, because it works in more than one context without being restyled. The third group is smaller and deliberately narrower, dresses, for the decisions you make after the main one. None of this needs the whole group. One piece from each is usually enough.

There are 20 pieces here from 14 brands, $62 to $495, all in stock when this was written. We would not buy all of them, and neither should you. shop-resa.com's Monica Blouse in Sky at $62 is the low-risk way in, and normakamali.com's GUNMETAL STUD SLEEVELESS JUMPSUIT at $495 only makes sense if this is a category you already use constantly. Read as a set, they get you close to Date Night Toos without any single purchase being compulsory. Nothing here is included because it is famous, and price is not used as a proxy for quality anywhere on this page. If you take one thing away: one considered purchase beats three hedged ones.