A boot for every ankle
Our favourite ankle boots for this year and every year hereafter
The first (and only) rule of wearing ankle boots is that you should never be able to see even a hint of skin between the top of the boot and the hem of your pants or skirt. Not a slice, not a sliver. We’re not usually one for rules in fashion, but this one holds fast no matter what day of the month you ask us. Anything else will look disjointed, halting the eye at that weird, ‘no man’s land’ part of the leg that not even Kaia Gerber could make work (probably…maybe).
Whether you’re wearing a full-length or cropped trouser, your hemline should — at the very least — slightly overlap with your boot. The one tweak we’ll accept to this is if you make a styling feature out of tucking your hemline loosely into the top of the boot, almost like a ‘French tuck’ for your pants. And leave the skinny leg + ankle boot combination back in 2012 where it belongs. In our opinion, the humble ankle boot is still paying the price for this crime in the court of public opinion!!
With these rare homeroom rules established, it’s worth noting that a great pair of ankle boots will be your most steadfast wardrobe companion (provided you buy well and care for them). Because, amongst all the trends that take up residence south of our shins, the ankle boot is relatively untouchable as a style, save for a few small tweaks to heel and toe silhouette. A classic low-heeled black ankle boot will always serve well as a foundation for risk-taking elsewhere in your outfit!
In this week’s newsletter, we round up the best ankle boots for this season and references for our favourite ways to wear them.
Below the paywall, you’ll find:
Our three favourite flat ankle boots
Five excellent pairs of low-to-mid heeled black ankle boots
Four good pairs of low-to-mid heeled brown ankle boots
Our three favourite pairs of higher heeled black ankle boots
Our three favourite pairs of higher-heeled brown ankle boots
Exclusive discount codes for our readers at ESSĒN, Nelson Made, Friends With Frank, Anna Rossi, Elka Collective, A.Emery and Reliquia
Flat Ankle Boot
Toteme did a lot for the old ankle boot when they released their sock-like flat boots, creating an instant classic that has been copied by just about every footwear brand down the line. This slip of a style, with a basically non-existent sole, is the more contemporary version of the flat ankle boot right now. The more classic and robust riding-style ankle boot still works, too — the key is to opt for hyper-minimal, clean and polished options.
SCANLAN THEODORE / Ballerina Boot — $900
COS / Leather Sock Boots — $350
AEMERY / The Grace Boot — $750
Styled with pants and jeans; a looser hemline and a slim-fitting boot
How we’d wear with skirts — note the length of the hemline, always covering the top of the boot.
Now for a little heel
The hardest working pair of shoes in your wardrobe — and ones you should have for years and years. Look for quality leather (or vegan leather if that is your preference) and a heel you can tolerate stomping around in for hours. Whether it’s a chunky, more western-leaning silhouette or a slimmer, kitten-like peg, look for a slightly curved heel that extends the back of the line from the heel to the floor.
