The 2 Bags I've Worn Most This Winter
And what my grandmother, Dorsey, taught me about personal style.
Dear Reader,
The summer my parents divorced I called Dorsey, my grandmother, and asked her if I could live with her for the summer. Two weeks later I showed up on her doorstep with two suitcases and stayed until September.
You learn the most intimate details of someone’s life when you live with them.
Every morning Dorsey walked into the kitchen in a one piece bathing suit and a silk robe. She’d made a smoothie from scratch and then I’d watch her take her vitamins. She would leave her leftover smoothie in the fridge for me. Then she would walk down to her pool to swim laps. My grandfather didn’t like for her to swim alone so he would ask me to sit by the pool and watch her. She was annoyed by it. I learned how to make myself scarce but keep an eye on her.
That was the summer she went out of town and I somehow drained half of her pool. Then scraped my grandfather’s car pulling into their garage. I ruined her perfectly white towels with my spray tanner. I broke a few glasses from her vintage bar. I was a wreck. But it was still the summer she let me borrow all of her sweaters. Carry her handbags. Wear all of her jewelry.
That was the summer I noticed how my grandmother lived in her clothes and her home, too. Her wide legs trousers. Her oversized blazers. She would settle on a few pieces a week to wear more than once.
Every single thing that she wore was classic. From the cut and color to the fit and fabric. From her wallet to her handbags. At 85 years old she elegantly wore things she must have bought in her 50’s. There is a Burberry trench coat that she purchased in the 90’s while on a trip to France with my aunt that I’ve been looking for all over the internet.
My aunt recently told me that at the end of Dorsey’s life she would walk around her house with her and point out how much she loved so many things in her home. From the design of her entry way stone (my grandfather designed their house) to the details she probably stopped noticing over the course of the 40 years she lived there (Dorsey passed away at 96 years old, in her home, with her husband).
This past week a member of the DORSEY executive team sent a team Slack with a link to Ezra Klein’s most recent podcast called How To Discover Your Own Taste. If you’ve not heard it yet, I highly suggest a listen on your next walk or drive to work.
For the first time in a very long time, it feels like a conversation around personal style (as it relates to all areas of life) is sparking again.
The world is a more interesting place when we’re all ourselves.
Dorsey was a notoriously private person (she never let anyone take professional photos of her beautiful home). In fact, no one in her family knew her age for many years (she hid her drivers license from everyone for two decades). But I’ve convinced myself that she wouldn’t be upset if I shared this photo of my cousin getting ready for her wedding in her bathroom (wearing her white silk robe, as described above, one of many from her silk robe collection).
I think if there is one thing that Dorsey taught me it’s to lean into what speaks to you. From you trousers to your planter pots. From your bathroom tiles to the fit of your coat. From your manicure (or lack thereof) to your tea cups. Find the pieces and things you love so much that at the end of your life you’ll still look it them and feel joy.
This weeks column is mostly dedicated to a series of lived in bags and coats you’ve seen many times before (but I’ve added the links again to make finding them easy). It’s January. For the most part, I lean into DORSEY jewelry during the depths of winter to make old things feel new until winter begins to thaw. And I should note here that I the point of my substack will not be to share new things each week. Rather, I’ll be focusing more on how I wear some of the same pieces (and some new ones) throughout a season.
As usual, I’m going to remind you that you probably don’t need anything in this email. But if you’re looking for something similar, perhaps this column may help you find it, or send you in a new direction altogether.
This week marks the true one year anniversary of this newsletter. Thank you to the (nearly) 10,000 of you who continue to read it each week. I’m still figuring out the format of this substack. If you have feedback, send it, I’d love to hear more.
Thoughts or questions? See you in the comments section.
As always, you can reach me directly at Meg@ShopDorsey.com.
All my very best (and talk soon),
Meg Strachan
Editor | What I Put On Today (WIPOT)
What I Put On This Week:
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Every time you write about your grandma I am madly inspired. I didn’t have an influence like this in my life so I’m adopting yours. Tell us all the stories 🫶
I love your stories about Dorsey. She sounds like someone who led an authentic and rich life who wasn’t afraid to enjoy the beauty and walk through the tough parts. I also love the idea of waiting to buy things you truly love and enjoying them for decades. Thank you for this inspiring piece of writing.