The short answer on Is Dooney and Bourke Better Than Coach is below, and the honest version is that it depends on two or three things rather than one. A strap drop under 22cm will not clear a winter coat. Unlined canvas is lighter but shows every mark; treat it before first use. Leather darkens where your hand sits, which is not damage; it is the bag settling. 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: L Space's Coastline Beach Bag - Natural Black at $136, and meliebianco.com's Hazel Nude Recycled Vegan Leather Tote Bag at $125. The first is the considered buy; the second is the one to start with. A strap drop under 22cm will not clear a winter coat. 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, Ann Demeulemeester's AD Small Shoulder Bag ($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, 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 10 brands, $28 to $385, all in stock when this was written. We would not buy all of them, and neither should you. awaytravel.com's The Luggage Tag in Matcha Milk Green at $28 is the low-risk way in, and Eric Javits's Querida Leather Crossbody Bag at $385 only makes sense if this is a category you already use constantly. Read as a set, they get you close to Is Dooney and Bourke Better Than Coach 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.