At 67, I Stopped Wearing Trousers That Dug in at the Waist All Summer
A LETTER FROM A READER
AT 67, I STOPPED WEARING TROUSERS THAT DUG IN AT THE WAIST ALL SUMMER
Margaret PembertonBoston · August 6, 2026
I almost didn't post this, because they're only a pair of trousers. But my friend asked where they were from at lunch, and then my daughter did, so I'll just say here what I told them.
For years, summer trousers were a small daily misery. The smart ones had a hard waistband that dug in the moment I sat down to eat, so I'd undo the button under the table and hope no one noticed. The comfortable ones were shapeless and hot. Either way I spent the warm months either pinched or perspiring, and I'd started reaching for the same dark trousers I'd worn for a decade.
"I didn't want to unbutton my waistband after lunch anymore. I wanted to forget my trousers were there."
HOW IT HAPPENS
Nobody decides to give up on comfortable, smart trousers. It goes one pinched lunch at a time. The tailored pair digs in, so you wear it less. The baggy pair is cool but shapeless, so you live in it. Before long the whole drawer is dark and forgettable, and you tell yourself that's simply what's practical now.
WHAT I HAD WRONG
I'd assumed comfortable and smart couldn't live in the same trousers at my age. The Kendra is the first pair in years that doesn't ask me to choose. They're from Bennett Boston, an American label that's been quietly looking after women our age for a good twenty years.
They're a lightweight, breathable summer trouser with a soft elastic waist and a discreet drawstring — no hard band, no digging, no undoing anything after lunch. The relaxed straight leg has a gentle drape that looks tidy and put-together rather than baggy, and there are proper side pockets, which I'm always grateful for. They keep me cool, they don't crease in a suitcase, and they slip on like something you'd laze in but look like something you'd wear out. I have the soft blue stripe, and they also do black and grey.
WHAT HAPPENED AT LUNCH
I wore them to lunch and sat through the whole thing without once thinking about my waistband — which hasn't happened in years. My friend asked where they were from, and my sister, who has never willingly complimented me in fifty years, said they looked smart. The next morning I had them on to walk my dog, Biscuit, and felt just as easy. That's the whole thing at 67 — trousers for lunch or for the dog, and you feel like yourself either way.
THREE THINGS I'VE LEARNED SINCE
An elastic waist is not a surrender. It's hidden and soft, and the trousers still look tailored from the outside.
A straight leg keeps it smart. The gentle drape reads as put-together, never baggy.
Cool and uncreased gets worn. They don't crease in the case and don't cook me in the heat, so I actually reach for them.
ABOUT THE PRICE
I'll be honest about why I'm writing this rather than just telling my sister. The Kendra is currently $44.95, down from $90 — half off for their summer sale — and when I checked this week the middle sizes were already going. They cut them from a US 2–4 up to a US 24–26, in the soft blue stripe, black and grey.
Kendra | Lightweight Summer Trousers
- Soft elastic waist with a discreet drawstring — no digging in
- Relaxed straight leg that looks tidy, not baggy
- Lightweight, breathable, crease-resistant · handy side pockets
- Inclusive fit, US 2–4 to US 24–26 · blue stripe, black & grey · free delivery via USPS
Due to high demand for our summer sale, the middle sizes are selling first.
I haven't undone my waistband under a table since they arrived.
Margaret Pemberton lives in Boston with her dog, Biscuit. Bennett Boston has over 20 years of experience delivering timeless fashion rooted in American heritage.
This page is a paid advertisement for Bennett Boston.