Boots season is when a wardrobe starts to show whether it was planned or merely accumulated, and knee-high boots are the clearest test. They cover the awkward gap between a hem and the weather, give a simple dress some structure and make trousers feel considered even when the rest of the outfit is just a jumper. I buy them as a proportion decision first and a fashion decision second. The shaft should sit close enough not to collapse, but not so close that a skirt catches on it. With a midi hem, the top of the boot needs to disappear beneath the skirt or leave a clean strip of leg. Anything in between looks accidental. Leather is the first pair, suede is the textural second, and an over-the-knee shape only makes sense if you already know what you will wear it with. Check the sole and the heel before getting distracted by a beautiful finish. A boot that cannot handle wet pavements is not a fall boot, it is a very expensive indoor accessory. My sensible price band starts just under $1,000 and rises quickly for hand-finished leather and serious suede. The aim is not to collect every height. It is to find one pair that makes the clothes you already own look newly useful. Below, the knee-high boots I would spend money on this season.

Gianvito Rossi does the knee boot with the same clean line it brings to its pumps, so the shaft never looks bulky and the heel does not overwhelm the leg. Prices run from $1,995 to $2,750, which is a substantial spend, but this is the label to consider if you want one pair to survive several winters. The 20 leather knee boots at $2,295 are the most versatile starting point, while the riding leather knee boots are the flat option I would wear with denim and long skirts. The santiago 60 leather knee boots have a little more lift. For drama, the 45 over the knee suede boots and the glen cuissard 85 suede over the knee boots are the two to choose from, depending on how much leg you want the boot to cover.

The leather knee boot is the one to buy when you want the widest possible wardrobe mileage. A clean shaft and a restrained heel will work under a midi skirt, over slim trousers and with a dress that needs a harder finish. The medea leather knee boots at $945 from Aeyde are the sensible entry point, while the leather knee boots from Dries Van Noten have the kind of plain confidence that makes them easy to repeat. The nobilis leather knee boots from The Row are the investment version, with enough line to make a coat and jeans look intentional. If you prefer a sharper finish, the stiletto patent leather knee boots from Paris Texas are the evening choice. Keep the leather conditioned, but never soak it.

Suede knee boots make the season's longer skirts feel softer and are especially good with denim, cord and heavy knitwear. The towns embroidered suede knee boots at $1,290 from Nili Lotan bring detail without turning the boot into costume, while the clive suede knee boots from Khaite are the cleaner shape for everyday wear. The calassohi 90 suede knee boots from Manolo Blahnik give the leg a long line, and the pattie 85 buckle detail suede knee boots from Valentino Garavani are the pair for anyone who wants hardware to do the talking. The bead embellished suede knee boots from Brunello Cucinelli are beautiful but need a quieter outfit around them. Treat suede before wearing it, not after the first puddle.

This is the grid for people who want the tall boot without committing to one strict silhouette. The tee over the knee boots at $990 from Proenza Schouler are the most approachable place to start, especially with short hemlines and opaque tights. The crease leather knee boots from Lemaire have a softer, slouched line, while Toteme's downtown leather knee boots are the useful middle ground between a riding boot and a fashion boot. The rubber trimmed leather over the knee boots from Rick Owens are for a stronger wardrobe, and the suede knee boots from MM6 Maison Margiela offer a quieter route into the same height. Choose the pair that agrees with your existing hems. A boot cannot rescue a proportion you never wear.

These are the pairs that sit outside the neat leather, suede and height arguments but deserve a place on the list. The peyton leather knee boots at $1,595 from Church's are the practical purchase, with the sort of grounded shape that works under a wool coat. Gucci's boulevard horsebit embellished leather knee boots at $3,000 are the statement version, while the kate botta 85 leather knee boots from Christian Louboutin keep the line dressier. For something more unusual, the passeggiata layered suede knee boots from The Attico build texture into the shaft, and the rein it animal print pony hair knee boots from Herbert Levine make a simple black outfit do less work. The medea suede knee boots from Aeyde are the budget-conscious finish.

The best knee boot fit is decided by the calf, not the foot. Measure the widest part of your leg while wearing the tights or trousers you expect to use, then compare that number with the brand's shaft measurement. A zip that stops halfway up is not a styling detail, it is a warning. I also prefer a boot with a little room at the ankle, because a perfectly tight shaft paired with a loose ankle can look oddly stiff. Use shoe trees or rolled paper to keep the shaft upright in storage, and never fold tall boots over a hanger. Suede should be brushed in one direction once dry. Leather can take weather, but it still needs time to recover between wears. Buy the height your clothes already support. Phoebe