A Letter From the Founder: The Orchard

A Letter From the Founder

A Comfortable Shoe Should Not Have to Announce That It Is One. The Orchard Was Me Refusing to Sell Another Pair That Did.

Six things I insisted on, why the toe is squared rather than pointed, and why they are going out at £42.95.

Emma Winslow
Emma · Founder of The Winslow Sisters · Richmond
September 2026 · 6 min read
The Orchard flats worn

My name is Emma. My sister Alison and I have had the shop just off the green in Richmond for eleven years, and shoes are the thing women apologise to me about.

They come in and they say, before I have asked, that they cannot wear anything narrow any more. Feet widen. It happens to nearly everybody and it is not a complaint, it is anatomy. And what the trade offers in return is a shoe that is genuinely comfortable and that looks, from across a room, like it came with a prescription.

So the choice on offer is: be comfortable and look it, or do not. I have watched women pick the second one and go home in pain, for eleven years. Six things came out of deciding that was not an acceptable pair of options.

1The toe is squared, not pointed.

The squared toe of the Orchard

This is the whole shoe. A squared toe puts the widest part of the shoe where the widest part of your foot actually is, across the joint, instead of tapering away from it. Nothing presses. It is a straightforward piece of pattern cutting and it is skipped constantly because a pointed toe photographs longer and slimmer, and a photograph is not a foot.

★★★★★ "Nothing presses across the joint, which is where every other flat I own goes wrong." Judith P., Guildford

2A real leather upper.

Leather gives where your foot pushes and then stops giving, so after a few days you have a shoe shaped to you rather than a shoe you are shaped to. Coated fabric does not do that. It never softens, and it never stops rubbing in the same spot. This is the single largest cost in the shoe and the first thing that goes when a buyer wants a lower price.

★★★★★ "Two days and they had given exactly where I needed and nowhere else. That is leather doing its job." Marion H., Harrogate

3A footbed that holds its density.

Anybody can make a shoe that feels wonderful in the first ten minutes. Soft foam feels marvellous and is flat by November. Ours is a firmer cushion that gives less on day one and is still there in the spring, which is the harder thing to sell and the right thing to make.

★★★★★ "Six weeks of daily wear and they have not gone flat underfoot. My last pair lasted a season." Angela T., Shrewsbury

4A sole thin enough to read as a flat.

The Orchard worn out walking

The moment you put a thick wedge under a comfortable shoe it starts to look like a health product, and then it only goes with trousers, and then it lives in the cupboard. The Orchard has a low flexible sole, so it goes under a dress as easily as under jeans and it does not add a category to your wardrobe.

★★★★★ "They go under a dress without looking like sensible shoes, which I had honestly stopped expecting." Christine W., Bristol

5One small piece of hardware, and nothing else.

The Orchard by the front door

There is a single gold emblem on the front and that is the entire decoration. No stitching detail, no bow, no contrast panel. One clean piece is what stops a plain flat looking like a plimsoll, and more than one piece is what makes a shoe look cheap. The restraint is the design.

★★★★★ "It is the one bit of shine on them and it is enough. Anything more would have spoiled it." Pauline M., York

6Five colours you would actually wear.

All five colours of the Orchard

Black, brown, olive green, beige and red. Not a novelty among them. The test I set was whether a woman could own two pairs without the second one being a whim, and the olive and the red both earn their place against the dark trousers most of us live in.

★★★★★ "I bought the black and went back for the olive within a fortnight." Linda B., Chester

Set against the two shoes you already own

The smart pair The comfortable pair The Orchard
Across the joint Presses Fine Fine
After four hours Comes off Fine Fine
How it looks Right Medical Right
Under a dress Yes No Yes
By November Still stiff Flat underfoot Shaped to you
The usual two pairs
  • One presses across the joint
  • One looks medical
  • Planning the day around which
  • Foam that flattens
  • A second pair in the bag
The Orchard
  • Squared toe, nothing presses
  • Reads as a proper flat
  • Leather that shapes to you
  • Firm cushion that stays
  • One pair, all day

Comfortable and looking comfortable are two different things, and the trade has spent thirty years pretending they are the same.

Why they are £42.95

Emma and Alison outside the Richmond shop

We buy in small quantities, and a leather upper across five colours and eight sizes is a large order for a shop our size. The Orchard came in at £130 and it is going out at £42.95. More than one pair and it drops again: 15% on two, 20% on three, 25% on four or more.

Two honest notes before you order. They come in whole sizes only, a 5 to a 12, with no halves; if you are a half size, go up rather than down, because the leather gives and the length does not. And they do soften over the first two or three days, so the first afternoon is firmer across the top than the second week will be.

£42.95Clearing price
5Colours
11Years in Richmond
30Day guarantee
Sally Chapman
One of our customers wrote to us about these at more length than I could fairly quote here.

"Every comfortable shoe I owned looked like it had been prescribed to me. I wore these for nine hours in London and took them off because I was going to bed, not because I wanted them off."

Sally Chapman · Farnham, Surrey
Read Sally's letter about the Orchard →

If a woman has to keep two pairs and plan her day around which one, somebody has failed her, and it is usually the person who cut the pattern.

What comes back to us is always the toe. If you have been keeping one pair for looking right and another for actually walking, this is where I would start, while the sizes are still there.

Orchard · Leather Flats

£130.00£42.95
Clearing price, save 67%
  • Squared toe, so nothing presses across the joint
  • Real leather that gives where you need it and stops
  • A firm cushioned footbed that does not flatten
  • A low sole, so they read as a flat and not a comfort shoe
  • Five colours · whole sizes 5 to 12 · Free UK delivery · 30-day returns
See if your size is still in stock →

The Orchard · £42.95 while sizes last

The last of this run is going now.
Take two and save 15%, three and save 20%, four or more and save 25%. Whole sizes 5 to 12 only, with no half sizes.
Free UK DeliveryOn every order
30-Day ReturnsYour statutory rights stand
Eleven YearsTwo sisters in Richmond

Emma, for Emma & Alison Winslow · Richmond

See the Orchard at £42.95 →

This is a letter from one of the two sisters who run The Winslow Sisters. Prices and sizes shown are correct at the time of writing and change as the run sells through. This page is a paid advertisement for The Winslow Sisters. The Winslow Sisters · Richmond · Free UK delivery · 30-day returns. Your statutory rights under the Consumer Rights Act 2015 are not affected.

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