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The Black Boot, Tested: Eight Pairs, One Winter

We bought eight pairs of black boots, wore them to work for a winter, and ranked them on comfort, durability and how they look on day ninety.

By Imogen Vale 3 min read
Eight pairs of black boots lined up in a row on a pale wooden floor, shot from above at an angle

Every autumn the same question arrives in our inbox: what is the black boot to buy? The honest answer is that it depends on your commute, your tolerance for blisters and how often you resole things. So this year we stopped answering from memory and bought eight pairs.

Over a winter, five of us wore them to work, to the station, to the supermarket and once, memorably, across a field. We kept notes. We scuffed them on purpose. We stood in puddles. Then we ranked them.

How we tested

Each pair was worn for at least thirty days before it was judged, and scored on five things:

  1. Comfort on day one, with no breaking-in allowed.
  2. Comfort on day thirty, after the leather had settled.
  3. Grip on wet pavement and on the kind of marble that railway stations seem to specialise in.
  4. Repairability, meaning whether a cobbler could resole them without despair.
  5. How they look on day ninety, which is the only test that really matters.
Notes on a Perfect Coat
Shoulders, length, lining and cloth: everything we have learned from a decade of wearing, repairing and arguing about winter coats.
Imogen ValeHighness

The four we would buy again

The Everyday Chelsea

Black calf, leather sole, elastic gusset that has not sagged in ninety days. Resoleable by any decent cobbler. £295

See it

The Lug-Sole Ankle Boot

The one for rain, hills and long walks. Waterproof lining, a sole that grips marble, and enough room for a thick sock. £240

See it

The Block-Heel Ankle Boot

Two and a half inches that you can actually walk in. Smart enough for a meeting, comfortable enough for the journey home. £320

See it

The Knee-High

A clean shaft that does not slouch and a zip that does not snag. The only knee-high we would call a staple. £410

See it

And the four we would not

Two were beautiful and uncomfortable in equal measure. One lost a heel tip in week three. One was perfectly good and perfectly forgettable, which in a market this crowded is its own kind of verdict.

👢
Our one piece of advice. Buy boots in the afternoon, when your feet are at their largest, and walk around the shop for ten minutes before you decide. If anything rubs, it will rub for ever.

Day ninety

The Chelsea, for the record, looks better than it did on day one. The leather has darkened a little at the flex point, the toe has taken a polish and the sole has that faint, comforting wear on the outer edge. That is what a good boot does: it stops looking new and starts looking like yours.

Imogen Vale

Written by

Imogen Vale

Fashion director. Writes about tailoring, the economics of getting dressed, and why most people already own enough.

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