A LETTER FROM A READER

AT 67, I BOUGHT A BOOT WITH A HEEL AND A FLASH OF RED — AND I FEEL WONDERFUL IN THEM

Margaret Pemberton
Boston · August 9, 2026

I almost didn't write this, because a woman my age is supposed to have talked herself out of a boot like this. But my daughter saw them on and said, "Mum, those are gorgeous," and I have to admit I felt rather pleased with myself — so here we are.

My boots had all gone sensible. Flat, round-toed, sturdy — fine for the shops, but I'd catch myself in a shop window looking exactly as practical as I felt. Somewhere in me there was still a woman who wanted a bit of glamour for a dinner out, and every time I saw something with a bit of edge I'd think, don't be silly, that's not for you anymore.

"I didn't want to look like I was chasing my youth. I just wanted to feel a little glamorous again — and to stop dressing like an apology."

HOW IT HAPPENS

Nobody decides to give up on a bit of glamour. It goes quietly. The sensible boot is the safe choice, so you buy the sensible boot. Anything with a heel or an edge feels like it belongs to someone younger. And year by year the fun drains out of the shoe rack until "striking" isn't a word you'd use about anything you own.

WHAT I HAD WRONG

I'd assumed anything with a heel and a bit of drama couldn't also be wearable at my age. The Tiffany proved me wrong. It's from Bennett Boston, an American label that's been quietly dressing women our age for a good twenty years.

It's a sleek black ankle boot with an elegant pointed toe, a striking oversized buckle across the front, and — my favourite bit — a flash of red on the sole that feels like a little secret. The heel is a sculpted shape rather than a thin spike, so it's got a bit more to stand on than I feared, and a handy side zip means I'm not wrestling to get them on. I wear them for dinners and evenings out, not for tramping round the shops, and for that they're perfect. I have the black. They make me stand a little prouder.

WHAT HAPPENED AT DINNER

I wore them to a birthday dinner and felt, for the first time in a long while, a little bit striking — in a good way. A friend clocked them the moment I took my coat off and asked to see the red sole. My daughter took a photo. Nobody thought I was mutton dressed as lamb; they thought I looked wonderful. That's the whole thing at 67 — a bit of glamour isn't undignified, it's a pleasure you're allowed to keep.

THREE THINGS I'VE LEARNED SINCE

A sculpted heel is friendlier than a spike. There's more to stand on, so I feel steadier than I expected in a proper heel.

One striking detail does the work. The big buckle and the red sole make the whole outfit feel considered — no need for anything else.

The side zip matters. They slip on with a zip rather than a fight — which, at my age, I do not take for granted.

ABOUT THE PRICE

I'll be honest about why I'm writing this rather than just telling my friend. The Tiffany is currently $64.95, down from $130 — half off for their season sale — and when I checked this week the middle sizes were already going. They do them in a US 5 through 9.5, in black and a soft beige.

Tiffany | Buckle Ankle Boots

★★★★★ 4.6 out of 5 · 420+ reviews

$130.00 $64.95 — Save 50%

• Sleek pointed-toe ankle boot with a striking oversized buckle
• A flash of red on the sole — a little glamour that feels like a secret
• Sculpted heel (steadier than a spike) and an easy side zip
• Sizes US 5–9.5 · black & beige · free delivery via USPS

See the Tiffany Boots →

Due to high demand for our season sale, the middle sizes are selling first.

I feel a little glamorous again — and it turns out that was never something I had to give up.