One brand, one category. What follows is Khaite only, ranked by price, so you can see exactly what each step up buys. The range runs from Ona Ankle Boot at $1280 to Petra Knee-High Boot at $2600, across 20 pieces. Most of the line is leather, which is what you are really choosing when you compare two pieces at the same price. If you are buying one thing, start at the bottom of the range and only move up when the construction and leather quality genuinely changes.

Sizing is the whole game in shoes. Order your usual size, walk on carpet for ten minutes indoors, and send back anything you are already negotiating with. The jump from $1280 to $2600 buys construction and leather quality, not a different idea, so decide how often you will actually walk in it before you pay the top of the range. Arizona suede ankle boots breaks in around your foot after a few wears, which is the version to buy if you want it to feel worn in rather than new.

Buy Clive Boot at $1680. It sits in the middle of the range, and the middle is where you stop noticing any improvement in construction and leather quality. Ona Ankle Boot at $1280 is the sensible first purchase if you have never owned one and are not sure how often you will walk in it. Petra Knee-High Boot at $2600 is the one to skip unless you already know the brand suits you, because at that price you will not walk far in them. Order your usual size, walk on carpet indoors for ten minutes, and send back anything you are already negotiating with. Shoes do not improve once you own them.