Fit is the whole question with Kenzo Ballerina Shoes. Get it right and almost anything else works. A strap across the widest part of the foot is what stops slipping, not a tighter buckle. A moulded footbed takes about a week to break in and then lasts years. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is strap placement, footbed and heel height. Everything else is preference. Two from the first group show the range: ALDO Shoes's Chicsneaker2 at $40, and Sperry's Classic CVO Sneakers at $30. The first is the considered buy; the second is the one to start with. A strap across the widest part of the foot is what stops slipping, not a tighter buckle. A moulded footbed takes about a week to break in and then lasts years. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

A flat sandal reads dressier with a longer hem. From the second group, shopakira.com's AZALEA WANG AMADA OLIVE COLORBLOCKED SPORTY BOOTIE ($90) 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, boots, 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, $30 to $270, all in stock when this was written. We would not buy all of them, and neither should you. Sperry's Classic CVO Sneakers at $30 is the low-risk way in, and Boden's Jessie Chunky Chelsea Boot-Leopard at $270 only makes sense if this is a category you already use constantly. Read as a set, they get you close to Kenzo Ballerina Shoes 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.