Strachan recalled the moment her grandmother gifted her three floral dresses after a trip out of town, which marked the beginning of her love for fashion and styling. “Even in a dressing room, if there’s someone next to me, I’m like, ‘Oh, I love the sweater. Have you thought about this?’ I love it, and I’ve always loved it. There was not another career for me, and there never will be.”
Dorsey, along with Strachan’s illustrious career in fashion, is a tribute to her grandmother’s legacy—an amalgamation of elegance, flair, and understated sophistication that now comes naturally to her. She embodies her grandmother’s sense of stealth wealth minimalism with a touch of panache every day, whether she’s in a business meeting or styling a shoot for her brand. Despite juggling the demanding roles of a mother and a CEO of an eight-figure company, Strachan carves out time to send out a weekly Substack newsletter titled “What I Put On Today”—a charming epistle of style and camaraderie where she shares her latest fashion musings to her readers. “I always say that if I didn’t do Dorsey, maybe in 30 years, the last job that I’ll ever have is probably styling. I just love it so much.”
Photo: Courtesy of Coliena Rentmeester
Sneakers, trousers, and an oversized blazer: the ultimate trifecta of comfortable cool
I like a more relaxed look. I have a daughter, so you know I’m running around a lot. And in general I like to be comfortable. I think the biggest shift for me is that I used to wear high heels a lot. Now, I barely own high heels. I used to wear heels to work every single day when I lived in New York and even when I first moved to Los Angeles. But now, I don’t think I’ve worn a pair of high heels in maybe a month at this point. I pair a lot of my looks with sneakers and I just love this pair that I got recently from The Row.
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Photo: Courtesy of Coliena Rentmeester
Shop secondhand
I’ve been wearing this brown Saint Laurent bag with everything. I like a big tote to just throw everything in and go. You can tell that my bags really get used and get thrown around; they’re on the floor, they’ve never seen a hook in a bar. When I buy something I really love, I wear it a lot. A lot of the bags that I buy are secondhand and I buy a lot of them on The RealReal. I just bought an old canvas Burberry bucket bag and I love it. It was very affordable and I kind of found it on page 32 of The RealReal. I just love the hunt.
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Pick your accessories first
I love to have a stacked ear with a really basic outfit. The first thing I did when I was putting this look together was thinking about what was going to go in my ear, and then I thought about everything else. Most of the time, the first piece that you’re putting on is maybe a sweater, or shoes, or the pair of pants you want to wear. But to me, I really start with the jewelry. If I’m going to wear necklaces, I look for pieces that are going to work with those necklaces, or if I’m going to wear a big ring, I might go for a more simple dress. So for this stacked ear, I think an oversized sweater and a very basic pair of pants work well with it. I really think about the jewelry I’m wearing first, which I learned from my grandmother who, when she got dressed, put her earrings on first and then the rest followed.
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Photo: Courtesy of Coliena Rentmeester
Try to steer clear of looking at sizing
I feel like proportions for me are something that I really enjoy with picking out clothes. I try not to look at the size that fits my proportions, and I typically size up and get them tailored because sometimes, even if you know it’s your size, it just doesn’t fit the way you want to. I’m really happy now to tailor things to fit my specific frame and that’s only something I’ve started doing the last couple of years. I never would have done that 10 years ago. I always just sort of check whatever I have the size for. But now I buy anywhere from size four to size 12. And that’s been something that I think has made shopping much more interesting to me, because almost always someone will say, “Oh, that’s, that’s going to be way too big on you,” and I just like an oversized fit. I think what makes a piece of clothing feel luxurious is what I think makes it look right on my body and the way that it drapes. I’m very detached from the sizing of a piece of clothing, because paying no attention to sizing has been a really healthy way to just be who I am and dress the way I want to.
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Photo: Courtesy of Coliena Rentmeester
Don’t be afraid to wear white—even after labor day!
I think that choosing a one tone look is one of the easiest ways to get dressed. And I love whites, neutrals, and eggshell colors in winter. Living in California, an all-black look can be a little bit harsh at times. And so I wear so many white and off-white pieces. And I know there’s this rule of no white after Labor Day, but I think I wear as much white through winter as I do in the summer—I just take slightly warmer or cooler tones of white depending on the season.
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Photo: Courtesy of Coliena Rentmeester
You can find hidden gems at the men’s section
I play with sizing a lot, and I wear a lot of men’s clothing, and more specifically men’s blazers and socks. In the last couple of years I started taking things out of my husband’s closet, which honestly is becoming a bit of a sore subject. I told him, “God, I feel like in the last couple of years, because I’ve been taking your blazers, my closet has doubled in size.” And he said, “That’s so interesting, cause I feel like mine’s been cut in half.” I just love how great this blue suede men’s blazer fits. It’s oversized on me, but I love the way it looks. I think that as I’ve gotten older, I kind of know what I like and I really gravitate towards styles that are comfortable and timeless.
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