At 62, the comfy shoes that finally do not look like comfy shoes

A letter from a reader

At 62, the comfy shoes that finally do not look like comfy shoes

Six things that make these retro trainers the pair I reach for every day this autumn, from a woman who is not a fashion writer.

Caroline RichardsCaroline Richards · Customer · Nottinghamshire · 5 min read

Let me be plain about who is talking. I am Caroline, I am 62, I live in Nottinghamshire, and I have never once sat down to write about a pair of shoes in my life. But for years I had quietly made a bargain with myself that I am not proud of. Every genuinely comfortable shoe I tried on looked like a comfortable shoe, if you take my meaning, the beige, clumpy, sensible sort that quietly announces to the world that a woman has given up. So I chose vanity over my own feet and squeezed into pretty flats that ached by lunchtime, rather than be seen out in what I thought of as a granny shoe. This is not a review. It is a woman who finally found a shoe that is genuinely comfortable and does not look it, saying why.

What I found is from Nottingham Boutique, a small boutique that has been quietly dressing women our age for a few years now. They are called the Jessy, a smart retro trainer in khaki and white, the sort the young ones wear with their jeans. When the boutique later asked if they could put my letter up for others to read, I said yes, on the condition I could be completely honest in it.

I slipped them on that first morning, caught sight of them in the hall mirror, and looked, for once, like a woman who was off out and about rather than off to a hospital appointment. Then I walked all day and forgot I had them on. That was the moment it won me over. Read on.

The khaki and white Jessy retro trainers worn with jeans on an autumn street

Here is the little defeat I had made my peace with. Whenever my feet ached, and at my age they ached, the shoes that would have soothed them were the flat, wide, sensible sort that made me look ten years older, so I stayed in the nice ones and paid for it by teatime. I would rather have sore feet than sensible shoes, which when I write it down is a rather sad little bargain to have struck with yourself.

I had decided that a shoe I could walk all day in and a shoe I actually liked the look of were two different shoes entirely. I was wrong.

These are the first shoes I have owned that are genuinely comfortable and genuinely lovely at once, and having barely had them off since, I can tell you it comes down to six things.

The Jessy retro trainers laid out with jeans and a tote for autumn

Khaki and white, with a gum sole and a neat retro stripe. The kind of trainer you would not guess was the comfortable one.

1

THEY LOOK LIKE A PROPER RETRO TRAINER, NOT A GRANNY SHOE

This is the heart of it. Instead of the beige, clumpy thing I dreaded, these are a neat retro trainer, khaki and cream with a soft gum sole and a smart little stripe down the side, the sort the young ones wear. On my feet they look current and considered rather than sensible and ageing, so I feel like myself in them. After years of choosing sore feet over looking my age, having a comfortable shoe this good looking has quite changed things.

Close-up of the Jessy trainer, cream suede toe and taupe side stripe

Up close. Sand suede, white panels, a taupe stripe and a gum sole. Nothing sensible about it.

★★★★★

The first comfortable shoes I own that I am not embarrassed to be seen in. My daughter asked to borrow them. Nobody believes they are the comfy ones.

Christine B., West Bridgford
2

SECRETLY THE MOST CUSHIONED SHOE I OWN

Here is the trick of them. For all that they look like a slim retro trainer, underneath there is a soft, cushioned, shock-absorbing sole that soaks up every step, so a long walk or a day on my feet no longer ends with me aching and longing to sit down. My knees are the better for it too. Nobody looking at them would guess, which is exactly the point.

Feet up resting in the Jessy trainers with a cup of tea

Feet up after a proper walk, and not an ache in them. That is new.

★★★★☆

I have trouble with my feet and expected to have to wear something orthopaedic and horrible. These are like walking on cushions and they are pretty. I could have cried.

Pauline H., Arnold
3

THEY KEEP ME STEADY AND SURE-FOOTED

This matters more to me now than I would once have admitted. There is proper support built into them and a good grippy sole, so I feel steady and sure of my footing on the pavement and the path, and I am not forever watching where I put my feet. It has quietly given me back a bit of confidence when I am out and about.

Standing steady on an autumn path in the Jessy trainers

Steady on the path of a crisp morning. Grippy sole, and no wobbling.

★★★★★

So steady and secure on my feet. I feel sure of myself walking on wet pavements now, which I did not before. And they look lovely with everything.

Margaret E., Southwell
4

COMFORTABLE FROM THE VERY FIRST STEP, NO BREAKING IN

I braced myself for the usual week of blisters, and it never came. They were soft and comfortable from the moment I put them on, no rubbing and no breaking in, because the upper is light and gives a little and the inside is padded and kind. They are so light in the hand you would not believe it, and lighter still on the foot.

The Jessy trainers by the front door, ready to go

By the front door, ready to go. On and out, no fuss and no blisters.

★★★★★

Comfortable the very first day, no breaking in at all. So light. I wore them straight out for a whole day of walking and my feet were perfectly happy.

Dorothy S., Beeston
5

THEY GO WITH ABSOLUTELY EVERYTHING

The khaki and cream is such a useful, easy colour that they go with everything I own, my jeans, my trousers, even a dress on a milder day. I do not have to think about it, I just put them on and they look right. One comfortable pair that quietly finishes off whatever I am wearing rather than fighting with it.

The Jessy trainers worn with jeans, walking on an autumn street

With my jeans on an autumn morning. They go with the lot.

★★★★★

The neutral colour goes with absolutely everything. I have practically lived in them since they arrived. So easy, and I get compliments every time.

Eileen T., Newark
6

AN HONEST FIT, NARROW OR WIDE

Here is the last of it, and a real relief. They are kindly cut and give a little, so they sit comfortably whether your feet are narrow or on the wider side, which so many pretty shoes simply will not do. The laces let you get the fit just right, and the sizing runs honestly, so what you order is what turns up. They make a lovely gift too, if you have a friend who has made the same daft bargain I had.

The Jessy trainers on the feet, an honest comfortable fit

A kind, honest fit, narrow or wide. Laced up just how you like it.

★★★★☆

I have a wider foot and dread buying shoes. These fit beautifully and did not pinch anywhere. Comfortable, pretty, and true to size. I bought a second pair.

Maureen C., Bingham

These, against the sensible shoe you have been avoiding

You can spend years wincing through the day in pretty shoes that hurt, rather than wear a comfortable one, because a comfortable one means frumpy. I know, because I did. Here is the difference, laid out plainly.

The "sensible" shoe

Beige, clumpy and orthopaedic-looking

Comfortable, but ages you ten years

Announces that you have given up

The one you hide at the back of the wardrobe

Comfy or lovely, never both

The Jessy

A neat retro trainer the young ones wear

Just as comfortable, and lovely with it

Makes you look like you are off out and about

The one you reach for every single day

Comfy and lovely at once

About the price

The Jessy is £34.95 at the moment. It was £70.00.

I will pass on what the boutique told me, which is that with the autumn sale on they are going quickly and the middle sizes tend to sell first, so once they have gone it can be a wait for them to come back. Their words, not mine. What I can tell you from my side is that half price is usually where I start asking what is wrong with a thing, and for a shoe this comfortable and this pretty, I have found nothing wrong with it. They came quickly, they were comfortable from the first day, and they looked exactly like the picture, which we all know is not always the way.

And I do not trust perfect scores, so I read the reviews before I ordered. Just over three hundred of them, sitting at 4.2 stars, which sounded like real women rather than robots, so I read on. The same things I have just walked you through come up in them, over and over, in other women's words.

4.2 ★
From 300+ reviews
30 day
Returns
Free
UK delivery

If you have quietly accepted that comfortable shoes have to look like comfortable shoes, this is the pair I would point you to myself, while your size is still in stock. Go and have a look.

Caroline

The Jessy retro comfort trainers in khaki and white

THE JESSY RETRO TRAINERS

★★★★☆ 4.2 out of 5 from 300+ reviews
£70.00 £34.95
  • A neat retro trainer, not a "sensible" granny shoe
  • A soft, cushioned, shock-absorbing sole
  • Supportive and grippy, steady on your feet
  • Light and comfortable from the first step, no breaking in
  • Khaki and white, goes with absolutely everything
  • A kind, honest fit, narrow or wide, sizes UK 2 to 7
  • Free UK delivery and 30 day returns
See sizes

The autumn sale is on now, half the usual price. The middle sizes tend to go first.

About the writer. Caroline Richards is 62 and lives in Nottinghamshire. She is a customer, not a fashion writer, and she was not paid to write this letter.

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