The 2 Bags I've Worn Most This Winter

And what my grandmother, Dorsey, taught me about personal style.

Dorsey’s guest bathroom. This photo was taken in May when my cousin was married in her garden.

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.

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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).

Dorsey’s mosaic bathroom tiles and her perfume bottles & DORSEY lab-grown diamond and white sapphire earrings for Paige to choose from for her wedding.

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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.

Dorsey’s tea cups. My Christmas pajamas.

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)

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What I Put On This Week:

I had known about this handbag for quite some time but finally decided to invest in it after seeing it sitting on a chair at a coffee shop, a bit aged, and wrinkled. In the interim, I started selling my other handbags after realizing I rarely wore them, which was the best decision for me. This is the a link to my EXACT Margaux bag in 15 inches by The Row. The smaller clutch inside my bag is this Hunting Season clutch that I asked my husband for for Christmas. I often take this bag to work and I use it for travel and the key is that you cannot be precious about the leather. She gets better with wear and tear. I am most looking forward to carrying her in 5-6 years when she is most worn in. One note, this color way only comes out once a year. She tends to move quickly .

I first posted about this Sportmax coatt in August and she sold out on MyTheresa almost immediately. The buying team at MyTheresa emailed me to let me know that they were trying to find more stock for the readers of this newsletter but sadly, they weren’t able to find more of it. I'm linking here to a version of the same coat (in the same color way) with a slightly different belt. This coat is light enough for spring and heavy enough for winter (blizzards aside). I’m wearing size 36 but I considered a size 38 as well.

Pologeorgis Shearling in size smal (there is no reason to buy a shearling unless you are ready to wear it for several years), I was delighted to have it in the -10 degree weather, and I was looking for a like one like this one for five years. My balaclava is Almada the Label and I have this in two colors (grey and cream).

This is the Hunting Season clutch (once again). I throw her into my larger bag along with my wallet so that I have two bags that work for me in different ways. During my work week I will pull this clutch out of my larger bag to go get lunch or a matcha. She works in the evenings, too.

It’s a little hard to see her caramel color in this odd lighting but she is a great clutch for summer, too. My large wallet, phone, and even a small toy of my daughters fit in it.

Dorsey lab-grown white sapphire and lab created emerald cocktail ring next to my custom Dorsey lab-grown diamond Theodora ring.

Hi from my car where I’m wearing my navy J. Crew coat in size 10. And I’m seated next to a straw bag I prefer to carry with me when I take my daughter to the park (even in the dead of winter) with a few cookbooks (I like to look at recipes while she swings from the monkey bars).

Here is a link to a vendor on Etsy who does the most similar version to mine.

Lastly, perhaps it my age but never underestimate the power of a great thin black turtleneck. I'm wearing this one in size small. Trousers are old Loewe. All jewelry @DorseyOfficial

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1. On occasion I may use an affiliate link in a post and receive a very small percentage of a sale linked through this site.