The short answer on Silk Shift: pick one anchor piece, keep the palette to two colours, and let the shoes decide how formal the whole thing reads. One piece should lead and the rest should stay quiet; two competing pieces read as an accident. Proportion does more than colour: volume on top wants something narrow below, and the reverse. 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: elietahari.com's Milano Sculpt Dress at $448, and lagence.com's Inori Beaded Mini Dress at $508. The first is the easy entry point; the second is where the money goes. Lining is what stops a cheap fabric reading as cheap. 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.

Let the dress be the loudest thing you own that day. A belt turns a shapeless dress into a deliberate one. From the second group, A.L.C.'s Willa Textured Crepe Midi Dress ($350) 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 dresses here from 15 brands, $125 to $1125, all in stock when this was written. We would not buy all of them, and neither should you. summersalt.com's The Seafarer Swim Dress - Main at $125 is the low-risk way in, and lagence.com's Sutton Maxi Dress at $1125 only makes sense if this is a category you already use constantly. On silk shift specifically: the difference between the top and the bottom of this list is real but smaller than the price gap suggests. 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: if you would not buy it at full price, you do not want it on sale.