Ankle boots are the shoes that have to do the most work, so I judge them by proportion before detail. They need to sit cleanly under trousers, leave the right amount of ankle below a skirt and survive the walk between home and dinner. Fall is when the category earns its keep. My rule is to start with the hemlines I actually wear, then choose the boot height and heel from there. A narrow ankle and a modest heel are the safest combination, but a platform or a squared shape can be just as useful when the rest of the outfit has room around it. Leather is the first purchase because it takes weather and repetition. Suede comes next, once you know you will care for it. Details such as studs, croc effect or a high heel should be treated as a reason to buy that specific boot, not as proof that it will work with everything. I also avoid a shaft that cuts the leg at its widest point when I am wearing a skirt. The best pair disappears into an outfit until someone notices how well it has been built. Below, the ankle boots I would rely on from the first cold morning onwards.

Khaite makes ankle boots with enough shape to feel current and enough restraint to be worn repeatedly, which is the combination I want from a serious shoe. Prices run from $1,280 to $1,700, and the range covers polished leather, soft suede and a few useful heel heights. The colt glossed leather ankle boots at $1,380 are the starting point, with a surface that gives denim a little authority. The andee suede ankle boots are the softer option, while the marlene leather ankle boots should work with a long skirt without looking delicate. For more height, the bella suede ankle boots are the pair I would reserve for tailoring. The leather ankle boots are the least fussy choice, and that is often the one that gets worn most.

A leather ankle boot earns its price when it keeps a clean line after months of being worn with everything. The camion leather ankle boots at $760 from Our Legacy are the practical buy, with a grounded shape that does not need a precious outfit. The leather ankle boots from Lemaire are quieter and more refined, while the insopo 90 leather ankle boots from Manolo Blahnik bring a proper heel without turning into a party shoe. The sofie 35 snake effect leather ankle boots from Aeyde are a good compromise for anyone who wants surface interest at a lower price. If you prefer something more visible, the jill embellished leather ankle boots from Saint Laurent make the boot the point. Condition the leather and replace the heel tips before they become a problem.

Suede makes the ankle boot feel less severe, especially with denim, wool and the longer skirts that are back in regular rotation. The stassi suede ankle boots at $650 from Stuart Weitzman are the approachable pair, while the sofie 35 suede ankle boots from Aeyde offer a similar everyday logic at the same end of the price scale. The sally 75 suede ankle boots from Gianvito Rossi have the height for a dressier wardrobe, and the eldra suede ankle boots from Isabel Marant are the better fit for flat shoes and relaxed trousers. For a platform, the martine 110 suede platform ankle boots from Aquazzura are the statement choice. Use a suede brush, keep them away from salt and accept that pale suede is a commitment.

This is the group for a boot with a stronger point of view, whether that comes from the heel, the sole or the finish. The zipped leather ankle boots at $1,490 from The Row are the cleanest of the lot, while the nobilis suede platform ankle boots from the same label give a softer shape more height. The cowboy 30 leather ankle boots from Versace are for a wardrobe that can handle the reference, and the bettina 50 snake effect leather ankle boots from Paris Texas make a simple dress look less polite. The floral consultant croc effect trimmed leather ankle boots from Our Legacy bring texture without a high heel, while the trap snake effect leather ankle boots from Proenza Schouler are the best value here. Let the boot be the only loud thing in the outfit.

The shopping list is where the useful oddities live, the pairs that do not belong to one neat material or shape but have a reason to be bought. The woodrow suede ankle boots at $725 from Studio Nicholson are the quiet everyday option, and the cave leather ankle boots from JUDE are the strongest lower-price leather choice. The dallas 40 suede ankle boots from Paris Texas add a little lift, while the sofie 35 leather ankle boots from Aeyde are easy to justify as a second pair. For a more considered finish, the zimmy 40 suede ankle boots from Valentino Garavani have enough detail for evening. The sofia 95 leather ankle boots from Gianvito Rossi bring proper height, and Chloé's susanna studded leather ankle boots remain the recognisable statement option. Buy the pair that fills a gap, not the one that merely resembles the pair you own.

Ankle boots are unforgiving at the top edge, so try them with the hem lengths you wear most. A boot that works with jeans can look abrupt under a midi skirt. I like a little ankle space when the heel is low, but a higher heel needs a closer fit for stability. Wear new boots indoors with your usual socks, then add a thin sole protector before the first wet day. Keep a separate brush for suede, and let both materials rest between wears. My most-used pair is never the dramatic one. It disappears under trousers and still looks good at 8pm. Phoebe