Kitten heels are back: how to buy a pair you can walk in

The kitten heel spent a decade being the shoe your mother wore to a christening, and then it came back the way the best things do: quietly, on people with good taste, until the search data caught up. Google's Canadian fashion report this summer put kitten heels at a twenty-year high, with open-toe black kitten heels the single most searched style. Anyone who has tried to cross Queen Street in a stiletto understands why. A heel between three and five centimetres gives you the posture of a heel and the day of a flat, and in a city that walks to everything, that trade is the whole point.

The catch is that a low heel hides nothing. A bad stiletto at least has drama; a bad kitten heel is just an uncomfortable shoe at the wrong height. The difference between a pair you wear every week and a pair that lives in the box comes down to four details, all of which you can check in the shop.

The four details that matter

Heel placement. On a kitten heel the heel should sit directly under the back of your heel bone, not set back toward the edge of the sole. A heel that is set too far back tips you forward and wobbles on uneven pavement, which is most of Toronto. Stand on a hard floor, rock gently from heel to toe, and notice whether the shoe stays planted.

Toe shape and your actual foot. The pointed toe is the classic kitten silhouette and it photographs beautifully, but the point adds length in front of your toes, not room for them. If your foot is wide, look for an almond or soft square toe, which keeps the line without the pinch. The open-toe versions trending this year solve the width problem honestly, at the cost of a season of wear.

Pitch. Pitch is the angle the shoe sets your foot at. A three-centimetre heel on a stiff sole can feel steeper than a five-centimetre heel on a flexible one. Bend the shoe gently at the ball of the foot; if it barely moves, the pitch will feel sharper than the number suggests.

The upper. Leather that is soft out of the box will be soft on day one and loose by month three; leather that is a little firm will take two wears to give and then hold its shape for years. Patent is stiffer and shows every crease. Suede is the most forgiving on a narrow foot and the least forgiving in a Toronto slush puddle.

What to wear them with

The kitten heel is a proportion tool. It does its best work under a trouser that breaks just above the shoe, a midi skirt that stops at the slimmest part of the calf, or a dress with a hem that lets the heel show. It looks oddly formal with wide, floor-grazing trousers, which want a flat or a real heel, and it looks a little prim with a mini unless the rest of the outfit is relaxed.

For the office it pairs with the same tailoring you already own and removes the commute problem. For weddings it is the answer to every garden ceremony on grass, and for dinner it reads as considered rather than effortful. The slingback version, which Google also flagged as breaking out this year, is the easiest of all: it bares the heel, lengthens the leg, and forgives a slightly wide foot.

Buying them in Toronto

The strongest selections sit with the boutiques that buy footwear seriously rather than as an afterthought: the multi-brand shops of Yorkville for the European makers, and the independent shoe shops on Queen West for the mid-priced and the Canadian-designed. Browse women's heels in Toronto to see the current run, and read the Yorkville guide and the Queen West guide for where to walk in and try them on, which for a heel is the only honest way to buy.

Try them late in the day when your feet are at their largest, walk on the hardest floor in the shop, and do not believe anyone who tells you a shoe will stretch more than a half size. It will not.

Common questions

Are kitten heels comfortable to walk in?

A well-made pair is more comfortable than almost any other heel, because a heel under five centimetres barely changes the angle of your foot. The comfort comes from heel placement, toe shape and a sole that flexes, not from the low height alone, so a cheap pair can still hurt.

What height is a kitten heel?

Traditionally between three and five centimetres, with the classic somewhere around four. Anything above six centimetres is a low heel rather than a kitten heel, and anything under three is closer to a flat with a lift.

Can you wear kitten heels in winter?

In a closed toe, yes, on cleared sidewalks and for the indoor half of the day. Leather copes with cold and salt if you wipe it down; suede does not. Most Torontonians carry the kitten heels and wear a boot for the walk, which is the sensible answer from December to March.

Prefer to browse from your couch? within opens Toronto's boutique shelves on October 1, and the quizzes will read your taste in the meantime.