The short answer on Polo Match: 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: Faherty's Baja Maxi Dress - Kingfisher Stripe at $209, and Detoure's Solid & Striped - Long Sleeve Maxi Dress - XS (Like New) at $150. The first is the considered buy; the second is the one to start with. 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. 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, retrofete.com's Avielle Knit Romper ($398) 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 15 brands, $58 to $648, all in stock when this was written. We would not buy all of them, and neither should you. kennethcole.com's Ribbed Halter Sweater Tank at $58 is the low-risk way in, and ronnykobo.com's Dorian Skirt at $648 only makes sense if this is a category you already use constantly. Read as a set, they get you close to Polo Match 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.