Henri Matisse, The Painter’s Family, 1911
The first time I encountered Leandra on the Internet was when her blog, Man Repeller, went viral in 2010. Back then, it consisted of Leandra posting pictures of her outfits and outfit philosophy. My favorite type of post involved her demonstrating the construction of an outfit. In the first image, she’d be wearing a something simple, like a nude dress that resembled Carrie’s Naked Dress in SATC, and then in the subsequent photos more and more layers would be added, until you ended up with something like (I’m approximating here) a jacket-sweater-jacket sandwich with four watches. This series was called “From Man Getter to Man Repeller,” because in addition to being cool Leandra is extremely funny.
Now, Leandra and I don’t share a ton of surface-level similarities. While she grew up in an Orthodox Jewish household in Manhattan I was growing up in an atheist Chinese-Canadian household in Surrey, British Columbia. While she was a college student literally becoming famous for her sense of style I was busy being a sophomore in a high school with, uh, absolutely no sense of style. Even while pregnant Leandra can make, let’s say, a dress layered over capris paired with complicated Dries van Noten sandals look elegant, whereas this will simply never be possible for me.
However!! There was something so essentially joyful in Leandra’s approach to dressing that touched the core of my being, and was inspirational to not only me but a whole generation of girls. I know this to be true because a couple years ago Leandra and I were getting lunch (I think in East Village?) and a fashion student came up to say hi to her and I could see from five feet away that she was literally crying and shaking. This is the impact that Leandra has. And personally, while both my life and my sense of style have changed wildly in the decade plus since I first started reading Man Repeller, I still read The Cereal Aisle every week and am inspired by her philosophy of style, which I interpret as dressing in a way that feels fun and inventive while also drawing on what’s familiar and comfortable for you, and is aimed not towards the male gaze but rather back inwards at yourself and reflected to others of any gender who resonate with what you’re trying to communicate about who you genuinely are.
1. I loved Man Repeller, and I love The Cereal Aisle. Can you talk a little bit about the shift from writing about style on the website to writing about it on Substack? Do you relate to writing differently now?
I think because my writing is so personal, even when it doesn’t seem that way, the difference is reflected in my own shift in understanding of what style can bring to you life. I have always known that it’s really important to me, and I have never subscribed to the idea that it’s shallow or hollow or negligent or wrong to care about it, but I didn’t really examine these ideas until I started writing on Substack. I had to, in a way, go through a process of rigorous examination and investigation to land back in the same place I have always been: in genuine belief that one’s relationship to clothes can be spiritual, deep and raw.
As far as how I relate to writing, I think the shift is probably similar in that I’m more aware of what writing does for me and when I hold that up against its impact: it’s much easier to make decisions about what is worthwhile to share and what still needs time to come around a bit further.
2. How has writing online affected the relationships in your life?
I like this question because the answer is yes but probably not for the reason you’d think. There might be this idea that writing personally online could create more depth in your relationships, but I have actually found the opposite to the extent that when you share a lot online it sort of gives you an excuse to work less hard to strike connection in person. Like in an unconscious way you might have this idea that because you explain yourself so thoroughly online you don’t have to do it in person. Recently I realized that resting on the laurels of my digital output actually corrodes the chance opportunities for genuine connection IRL. It takes real effort to connect with friends, no matter how close you are. There’s a real vulnerability you have to bring to the table, and also a level of focus. It’s work, but the pay off is worth it.
3. Could you tell me about one friendship that’s been really meaningful for you in the past few years?
I have a friend I have known since I was really young, who is really similar to me: we’re both daughters of middle eastern (Persian) immigrants and that creates such an immediate connection. She was a grade older than me in school when we were growing up, and weren’t very close though our families knew each other but reconnected after college and started to build a real friendship. I’ve been thinking about her a lot with a sense of gratitude because I think she’s the first real friend I’ve had. That in a way she taught me how to be a friend by being one herself. She’s so supportive and genuinely happy to see her friends grow and rise and fill into themselves. It’s hard not to feel the same way in response, and after time that dynamic becomes its own sisterhood. I’m always thinking about her and praying for her and genuinely want for her happiness the way I do my own daughters and it occurred to me recently how rare it is to have friends like this. The American female experience is not such that we learn this kind of communion and support. Generally speaking, I think the way women can and should lead each other is not by standing “leader” above “followers,” that’s too patriarchal but by standing in a circle on the same level together.
4. What’s one way that friendships (or one particular friendship) has challenged you? Whether it’s through conflict, friendship breakups, or relating to people in a new way.
A lot of unwanted feelings come up in other friend dynamics I maintain — competition, jealousy, the illusion that there are winners and losers, that one person’s success directly correlates to how much success I can have and even if intellectually I know none of this is real, a lot of it still needs to integrate. They’re very uncomfortable feelings to sit with, ones I resent and want to shove down but I also recognize that acknowledging them and expressing them in whatever way feels appropriate gives me a chance to challenge them/make new choices/create new dynamics, so it feels hard and bad in the moment, and incredibly unnatural too but I never regret pushing through.
5. What does aspirational friendship look like to you, and how does it intersect with other areas of your life like motherhood/marriage/work?
Sisterhood for sure — I know you haven’t asked specifically about female friendships but it’s a topic that’s been on my mind a lot and I think for a lot of us, it can be a sort of balm or savior. I do have a fair amount of male friends too but the dynamics, for whatever reason, feel less complicated.
I have about 3 female friendships that are kind of similar to the dynamic I described in your question #3. Each is really special in that some element of the friendship makes me a better person. Roxana (from question 3) has taught me how to be more supportive and nurturing. Claire (another close friend) teaches me expansion and joy and there’s a lot of humor and high energy in it too. Then my other friend Krissy really motivates me with her unapologeticism and supernatural force. For whatever reason it’s not threatening, it’s inspiring and exciting and it feels achievable.
Maybe I’ll end with a short meditation on what Leandra mentions about female friendship: the other day I was sitting across the table from a new female friend and I just thought, man, it’s so much more intimidating to befriend women because I care so much more what they think. I am deeply attached to the women in my life, and I want to impress them, and sometimes I’m a little scared of their judgement. In high school my two best friends were two girls named K and E (hi guys if you see this!!) and I remember us walking with arms linked from class to class, faces bent towards each other as we talked. We talk constantly, we’d do everything together. And we fought a not insubstantial amount. With girls, these questions come up in a way they don’t with men: you are compared to each other by others, you compare yourself to them, you’re way too invested in their choices, you only want the best for them, they get on your last nerve. It can feel claustrophobic. (Elena Ferrante’s Neapolitan quartet is the best depiction of this that I’ve ever, by the way.) But I’ve always felt confident only women can teach me how to be. Like what Leandra said about her belief that “one’s relationship to clothes can be spiritual, deep and raw”—it’s only in reference to other women that I can figure out what my values are, and what I hope that they’ll become.
This was such a beautiful conversation, thank you for letting us take part! Friendships, especially female friendships, is a endlessly fascinating topic, huh
So beautiful 😍