Boots are the one category where paying more genuinely buys you something. Not the logo, the last. A boot is a shoe built around the shape of a leg, and the brands that do it well are the ones that have spent twenty years refining a shaft width and an ankle break so the thing looks like it belongs to you rather than sitting on you.

So here is what I check before anything else. The shaft circumference, because a knee boot that gaps at the calf will never look right no matter how good the leather is, and a good product page tells you the measurement. Then the heel height against the heel type: a 50mm block will carry you through a day, a 95mm stiletto will not, and both are correct depending on what you are doing. Then the sole, since a leather sole is beautiful and needs a rubber topping added before you ever wear it out. And then the leather itself, where I want a smooth calf that creases rather than cracks, or a suede with a tight short nap that does not go shiny at the flex point.

This issue runs forty pairs from Net-A-Porter, split by material and by height, from around $745 to $4,000. Everything was in stock when I put it together.

Below, starting with the house I trust most on fit.

Gianvito Rossi is the answer when you want a boot that fits a real calf and still looks like a fashion shoe. The shafts are cut narrow through the ankle and released through the leg, which is why the 45 over the knee suede and the Zayne 20 sit flat instead of bunching. The Riding leather knee boot is the one I would buy to keep, the Santiago 60 gives you a walkable heel in a tall shaft, and the 70 suede Chelsea on a lug sole is the pair I would wear in bad weather. At the ankle, the Sofia 95 is a stiletto that is genuinely wearable and the Levy 55 in leopard print suede is the one that makes an outfit. Roughly $1,395 to $2,750.

The most useful boot anyone owns. Proenza Schouler's Slant is the architectural one and the cheapest here at $1,150. Bottega Veneta's Cherry has the squared toe that has quietly become the shape of the decade, Khaite's Marfa is the flat black boot I recommend more than any other, and its Sybil in glossed leather is the dressier sibling. Paris Texas's Bettina 50 is a clean western influenced boot and the Roxy adds hardware without tipping into costume. Saint Laurent's Jill Cassandre is embellished and still restrained. Nili Lotan's Joplin is a Chelsea, which is the shape I would pick if you only buy one.

Suede is the softer decision and it dresses down better than leather does. Aquazzura's Slouchy 50 has the drape that makes a suede boot worth it, The Row's Cindy is the quiet one and its Nobilis platform is the opposite. Khaite gives you both a kitten heel Bella and a flat Clive. Valentino Garavani's Zimmy is topstitched western, Aquazzura's Saint Honore in navy is the colour I would take over black, and Isabel Marant's Edrik is buckled and slouched and the most fun pair in the issue. Protect all of these before the first wear.

The tall boot is the one people get wrong, almost always on shaft width. Brunello Cucinelli's bead embellished suede and Dries Van Noten's leather knee boot are the two I would call properly cut. Valentino Garavani's Zimmt 60 is the sleek black option, Christian Louboutin's Loo 85 over the knee is the evening one and its Santiabooty 85 is western in suede. Manolo Blahnik's Pamfilo 90 is the elegant stiletto shaft, Paris Texas's El Dorado is a stacked heel knee high, and Gucci's Web detailed boot is the one you will still recognise in ten years.

Eight more across both heights and both materials, from around $745 upward, so there is something here if the pairs above are out of range. I would look at the flat leather Chelsea and the mid heel suede ankle boot first, because those are the two shapes that get worn until they die. Everything links through to Net-A-Porter.

Two things I do to every pair before they leave the house. A cobbler adds a thin rubber sole protector, which costs very little and roughly doubles how long the boot lasts, and suede gets two light coats of protector spray with a proper dry in between. Then cedar or even rolled magazines in the shaft so tall boots do not fold at the ankle in storage, because that crease never comes out.

On wearing them: a knee boot wants a trouser that either tucks in cleanly or clears the top of the shaft, and anything landing exactly at the boot line is what makes an outfit look short. Ankle boots are the opposite and forgive almost everything, which is why I always tell people to buy that pair first.

Phoebe