At 67, I Stopped Choosing Between a Dress That Was Comfortable and One That Looked Nice
A LETTER FROM A READER
AT 67, I STOPPED CHOOSING BETWEEN A DRESS THAT WAS COMFORTABLE AND ONE THAT LOOKED NICE
Margaret PembertonBoston · August 8, 2026
I almost didn't write this, because it really is just a dress. But three different people have now asked me where it's from, and I've told the story enough times that it felt easier to write it down once and be done with it.
For years I felt I had to choose. The comfortable dresses in my wardrobe were shapeless, sack-like things I only wore round the house. The ones that actually looked nice pinched at the waist or needed fussing with before I could face anyone. So most days I picked comfort, felt frumpy, and told myself it didn't matter at my age.
"I wanted to open the wardrobe, put one thing on, and feel both comfortable and like myself. Not one or the other. Both."
HOW IT HAPPENS
Nobody decides to give up on looking nice. It happens one tired morning at a time. The pretty dress needs an iron and a good foundation, so you skip it. The comfy one is shapeless, so you feel dowdy. Before long you're just getting through the day in whatever's least bother, and you quietly decide that comfortable and put-together aren't meant to go together anymore.
WHAT I HAD WRONG
I'd assumed comfortable had to mean shapeless, and elegant had to mean effort. The Colleen is the first dress in years that's neither. It's from Bennett Boston, an American label that's been quietly dressing women our age for a good twenty years.
It's a relaxed midi dress with a soft, easygoing shape that skims the body instead of clinging — so it's genuinely comfortable to wear all day, but it still looks polished when I walk out the door. The fabric feels lovely and soft, it moves with you rather than fighting you, and the length is exactly right: a proper midi that covers what I want covered. I have the navy, and it's become the thing I reach for without thinking.
WHAT HAPPENED AT LUNCH
I wore it to a lunch with friends, expecting nothing. Two of them asked where it was from before we'd even sat down, and one said I looked "well" in that way that means more than it says. I'd been comfortable the whole time — no tugging, no watching the clock until I could get home and change. That's the whole thing at 67: you want to feel easy in your clothes and still look like you made an effort. This does both.
THREE THINGS I'VE LEARNED SINCE
A soft shape flatters. It skims instead of clinging, so I stopped thinking about what was underneath.
Comfortable gets worn. Because it feels easy, I actually reach for it — not just on the days I'm staying in.
The length is right. A proper midi that covers the knee — I never once felt I was showing too much.
ABOUT THE PRICE
I'll be honest about why I'm writing this rather than just telling my friends. The Colleen is currently $49.95, down from $100 — half off for their season sale — and when I checked this week the middle sizes were already going. They cut it from a US 4–6 up to a US 24–26, in navy blue, brown, red and green.
Colleen | Relaxed Elegant Midi Dress
- Relaxed midi shape that skims rather than clings — comfortable all day
- Soft, easy fabric that moves with you, no ironing fuss
- Looks polished from the house to a lunch out
- Inclusive fit, US 4–6 to US 24–26 · navy, brown, red & green · free delivery via USPS
Due to high demand for our season sale, the middle sizes are selling first.
I feel comfortable and put-together on an ordinary morning now — and I stopped choosing between the two.
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.