The short answer on Red Shoes: 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. A stacked heel walks better than a block of the same height. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is shaft height, calf width and sole grip. Everything else is preference. Two from the first group show the range: shopakira.com's AZALEA WANG PURR TIGER FUR THIGH HIGH BOOT at $130, and showmeyourmumu.com's Billini Onndrea Boot ~ Cherry Tumble at $140. The first is the easy entry point; the second is where the money goes. A stacked heel walks better than a block of the same height. Measure your calf before buying anything with a shaft above the ankle. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

Boots want either a skimming trouser or nothing below the knee at all. From the second group, St. Agni's Soft Boot - Black ($529) 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, sneakers, 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 17 brands, $30 to $529, all in stock when this was written. We would not buy all of them, and neither should you. Sperry's Bermunda Slip-on Sneaker at $30 is the low-risk way in, and St. Agni's Soft Boot - Black at $529 only makes sense if this is a category you already use constantly. Read as a set, they get you close to Red 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: buy the one you can picture using this week, not the one you are saving for later.