Style Granny 14: Getting Back Into Skirts After 65: What Worked (and What Didn't)

Cover Your Bases #94

(Mostly, a pants person.)

Just to recap, I’m a former OG tech exec and old school blogger, now nonprofit development and AI focused, who started this newsletter during the pandemic. This fall, my interest in vintage fashion revived, and I added Style Granny, this series about finding and choosing clothes that make me feel good. Cover Your Bases switches it up, so thank you for reading.

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A baby bunion is a small thing that has, for years, made the footwear for skirts feel impossible. The challenge of deciding what to wear on my feet for each skirt shape, and the worry that my calves (and thighs) would look impossibly clunky without a leg-elongating heel, made it easier to focus on wearing pants. But then I started lifting weights, and something about it made me more willing to try skirts again.

The first skirt was very mid-century modern — a cotton-print mini with a small pattern repeat in turquoise blue and bright, clear red on a white background. I wore it in Palm Springs in February with printed leather sandals and my new chambray button-down. Not too tight, not too loose, it gave me real freedom of motion — very different from the loose linen trousers that were central to the rest of the trip.

Then, in March, I took another new-to-me skirt on a family trip to Texas. This one was a vintage black cotton Talbots Petites A-line skirt with Greek-style silver embroidery. It felt more versatile than the mini; it would look great with a big, glitzy belt and a black rock T-shirt, or with my silver metallic Paul Smith V-neck sweater. On the Texas trip, I styled it with a black Vera Wang rock tee and a white button-down as a light jacket. That night, among my family of fashionistas, I felt like I held my own.

As I get into spring and summer skirts, I’m also thinking ahead to fall. When I discovered that Talbots Petites has an equestrian line (WTF?), I dug deeper and found some genuinely lovely pieces — including a corduroy mini in burgundy, forest green, and mustard with an equestrian motif. The pattern features bits and bridles, but it’s much more abstract (and less kinky) than that sounds. The color scheme is perfect for fall, and it fits well. My plan is cashmere crewnecks, flat boots, and — for the first time in years — colored tights.

The skirts that worked were all either A-line or straight, hit at or above the knee, and none required heels. The fourth — a Quince black silk slip-dress-style skirt I bought a couple of years ago and genuinely love — somehow never gets worn. It could be that black satin feels too dressy and needs to be roughed up with a button-down and a band tee (doesn’t sound like me). Or that it’s waiting for evenings and date nights, paired with my black chiffon Ruti blouse, which I also rarely wear.

Shoes made the difference

As for the footwear, what changed? Erin’s Blackbird SpyPlane recommended La Plume sandals: I got an inexpensive pair in brown—they were great—and then a second pair in black—problem solved. I decided that wearing fuller skirts, like the black embroidered skirt, with bigger shoes would be fine. Allbirds and Merrells with skirts.

The silk skirt is still in the closet. The sandals are by the door.

Thanks for reading this issue of Style Granny, it’s been so fun to write. And if you enjoy it, please subscribe,

Best, Susan