A long time ago, when I was still in my assistant days at Lucky, I used to cobble together some pretty experimental outfits. I was a tad more fashion-forward back then (my old boss, Kim France, would probably describe it as “costume-oriented”), and didn’t really have any money to spend on clothes, so I would wear a lot of zany vintage pieces—all at once. After a particularly painful break-up (I got dumped), I went to Connecticut for a weekend of crying my eyes out with my brother and his partner, Peter. Peter’s mother, a kind soul in a million different ways, bundled me into the car and took me shopping, where she bought me the first outfit in my entire life that made me look reasonably pulled together. And in that way that clothing can always inform your mood, it made me feel pulled together again, too. It was crisp white pants and a pastel, plaid Milly blazer that looked straight out of the ’40s.

I wore that outfit to work the following Monday—and felt like a not-so-miserable, ladylike version of myself—until I decided to walk to Pret a Manger for a sandwich with my friend Rumaan, and literally got TAGGED by a kid with a Sharpie on the corner of 42nd and Sixth Avenue. He drew all over my back. In indelible marker. I was upset for about 20 steps (in fact, I tried to catch him), until I started laughing. I mean, who gets tagged? Clearly, the universe didn’t approve of my newly-improved style. The best part is though, that even though I was a lowly (like super lowly) assistant, word got out to the Milly people that this happened to me, and they invited me to the showroom to pick out a new coat. True kindness. Whenever I need a pick-me-up, or just want to look like I know what I’m doing, or am missing Peter’s mother, this is the brand for me: It’s ladylike, subtly retro, and full-on polished.

MILLY “DIANE” RETRO COAT, $375.00, NEIMAN MARCUS; MILLY “DARCIE” PLEATED SKIRT, $395.00, NEIMAN MARCUS.