The short answer on Bottega Medium Andiamo: 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 strap drop under 22cm will not clear a winter coat. The groups below run from the decision that matters most to the ones you make afterwards.

What decides this is capacity, closure and strap drop. Everything else is preference. Two from the first group show the range: Anine Bing's Leah Hobo Bag Plain Raffia - Black at $425, and Isabel Marant's PRAIA SMALL SHOULDER BAG at $750. The first is the easy entry point; the second is where the money goes. Leather darkens where your hand sits, which is not damage; it is the bag settling. Unlined canvas is lighter but shows every mark; treat it before first use. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.

One structured bag does more work than three soft ones. Match the bag to the day, not the outfit. From the second group, Hammitt's Zoe Tote ($495) 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, bags, 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 bags here from 13 brands, $178 to $1890, all in stock when this was written. We would not buy all of them, and neither should you. awaytravel.com's Featherlight Diaper Tote in Jet Black at $178 is the low-risk way in, and Isabel Marant's BOLTON BAG at $1890 only makes sense if this is a category you already use constantly. Read as a set, they get you close to Bottega Medium Andiamo 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: pay for the thing that touches your body and economise on the thing that sits on top of it.