The short answer on Whistles Leather Bag is below, and the honest version is that it depends on two or three things rather than one. Cost per wear is the only figure that matters, and it favours the plain expensive thing over the interesting cheap one. Price splits into materials, labour, volume and brand margin, and only the first two are visible in the product. Unlined canvas is lighter but shows every mark; treat it before first use. 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: Radley London's Elm Avenue Leather Small Ziptop Cross Body Bag in Black - 112646 at $77, and J.McLaughlin's Dinah Leather Card Holder in Crocodile at $50. The first is the considered buy; the second is the one to start with. Leather darkens where your hand sits, which is not damage; it is the bag settling. A strap drop under 22cm will not clear a winter coat. 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, Radley London's City Road Leather Large Flapover Shoulder Bag in Black - 112409 ($95) is the one that earns its place, because it works in more than one context without being restyled. The third group is smaller, and it is there 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, $27 to $428, all in stock when this was written. We would not buy all of them, and neither should you. Eddie Bauer's EB Signature Top Stitch Leather Passcase Wallet at $27 is the low-risk way in, and Mac Duggal's Black Medium Croc Embossed Leather Handbag at $428 only makes sense if this is a category you already use constantly. On whistles leather bag specifically: the difference between the top and the bottom of this list is real but smaller than the price gap suggests. 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: the piece you reach for on a rushed morning is the one that was worth the money.