Cheryl Shops

There is a Thing happening on the internet at the moment, and it's the Coastal Grandmother aesthetic. Think of a heroine in a Nancy Myers movie: book clubs, farmers markets, Carole King, a glass of white wine (or three), and airy linen clothing. As someone who enjoys all of the above, it's a lifestyle I can definitely get behind, especially when it comes to the clothing part. When the weather gets hot, I love a loose-fitting linen dress that the air can just breeze right through, and of course it gets chilly along the coast at night, so you'll want to have an organic cotton sweater on hand. I'll take loose and relaxed over short and tight any day—the better to eat my heirloom tomato and burrata salad in, right? Thankfully I live in a city where the Coastal Grandmother game is strong, and there's no better place to shop for it than Margaret O'Leary, which opened its first store on Claude Lane in San Francisco over 25 years ago and can now be found across the country (including in my hometown, Chicago). They invited me to pick out a few of my favorite pieces, and as soon as I put them on, it was like a glass of sauvignon blanc showed up in my well-moisturized hand and "This Will Be an Everlasting Love" started playing. Here's my interpretation of the Coastal Grandmother aesthetic.

Margaret O'Leary Charlotte dress (love this one too) 

While one could argue that the true Costal Grandmother uniform involves khakis or wide-leg pajama pants—and there's certainly a time and place for those—I personally gravitate toward a sundress in the summer. I am obsessed with this tiered linen dress, and apparently I'm not alone, because it's now sold out (sorry!). I love that it's fitted in the shoulders and bust, so that I'm not drowning in fabric, not that a Coastal Grandmother would ever apologize for that. Linen is a famously temperature-regulating fabric, making it perfect for both hot days and cool nights, and, shall we say, women of a certain age (hey, I'm getting up there myself). This one allows air to flow through it beautifully, and I will say, be careful if there's a sudden gust of wind, as it certainly is swingy. In spite of Coastal Grandmother fashion having a shapeless reputation, Margaret O'Leary clothing is very well tailored and runs true to size (e.g. there's no vanity sizing here). I'm wearing my usual size small and it's just right. And as for the color, duh, it's blue as in the ocean.

Margaret O'Leary denim jacket

Margaret O'Leary got her start as a knitter, so when it comes to sweaters, she knows what she's doing. I say sweaters because in spit of its name, this is not actually a jacket but a double-knit organic cotton cardigan that looks like a denim jacket. It's the perfect weight for coastal living in the summer—it's thick enough to keep you warm when you need it, but it's not so heavy that you're going to sweat in it. The shape is slightly boxy and works with everything from a voluminous dress, as I'm wearing here, to over a T-shirt and jeans, which is how I tend to wear it the most IRL. This cardigan measures "soft" on the Margaret O'Leary Softness Scale (and yes, the fact that they even have such a measurement is the most Coastal Grandmother thing ever) and also comes in—I'm not making this up—a color called vanilla. It runs true to size; I'm in my usual small, and it's perfectly roomy without being sloppy or shapeless. 

Chloe Faye bag & Silent D boots

On one level, neither of these accessories is very Coastal Grandmother—a canvas tote bag and Birkenstocks would be more accurate—nor are they from Margaret O'Leary. However taupe is a very CG neutral, and wearing boots in summer seems very characteristic of a woman who gets chilled when it's 72 degrees outside, not that that woman is me, ahem. Plus, part of the beauty of Coastal Grandmother-ing is that you can interpret it in your own way, and mine is slightly more dressed up. By the way, I bought these Silent D suede boots at Anthropologie after giving up on the Isabel Marant Denvee boots, and I love them. I hate boots with zippers, and suede can often be too slouchy without them, however these are perfect. They run true to size, if a bit narrow—I got the 39 in a wide width (note: it's the foot, not the calf) and they're just perfect. Which is just how a Coastal Grandmother likes her shoes!

OUTFIT DETAILS: Margaret O'Leary Charlotte dress (c/o) (love this one too) | Margaret O'Leary denim jacket (c/o) | Chloe Faye bag | Silent D boots

Visit the Margaret O'Leary store at 2400 Fillmore Street if you're ever in San Francisco (or my neighborhood)!