On a recent family trip to Palm Springs, CA, my husband and I decided to eat at the Jonathan Adler-designed, psychedelic, Rat Pack-inspired restaurant, Mr. Parker’s. The restaurant wasn’t exactly us, but the womanizing, drunk historical feel of the place had alluded us up to that point. Even the motel we stayed at was a ranch-like oasis with a barn, pool, and no televisions in the rooms. Mr. Parker’s was a purposeful roadside carnival — albeit an expensive one — a symbolic representation of old school Palm Springs that we didn’t want to miss. Except I felt intimated. In New York, black jeans, booties, silk top, and blazer would work in pretty much any restaurant, but Palm Springs was a whirlwind of prints, silks, and flowy garbs. Would every woman be in a Tory Burch orange-and-yellow Greek-key patterned dress? I follow Martyn Lawrence Bullard’s Instagram and his posts from Palm Springs are filled with electric pinks, blues, and geometric-mirrored wallpaper, like the kind my mother decorated our house with in the ‘70s. What do you wear to such a place? That’s when I remembered my new purchase: A jet-black, floor-length linen caftan from the No. 6 store. If I’m being honest, it’s more like a black tent. The only design element is the black-on-black edging along the V-neckline. I brought it along on the trip because I had a desert goth fantasy about wearing full-black in the stark sunshine. I even dragged my unimpressed sister-in-law out to the desert so she could take pictures of me in it, and suddenly, we — the caftan, the desert, and I — reached fashion symbiosis. The dress and the desert both lacked structure; they were both mysterious. You can disappear in both, and I did, which made me fall in love with it even more. “I’m wearing my new dress,” I said to my husband. “Really?” he said, a little skeptical. “Caftans are super in style right now,” I assured him, though that’s not why I was wearing it. It seemed so obvious that it would be the right statement piece — overflowing, shapeless, decidedly unflattering. But I was wearing it because, as Rachel Syme wrote in a piece detailing the importance of the caftan, it was a “body-swallowing masterpiece.” I no longer had to worry about my shape, about the sag under my arms. I’d fade out in my unflattering caftan and my persona would rise like a phoenix, because the kind of person who could walk into a place like Mr. Parker’s wearing a black tent, really, can do almost anything. When you feel empowered by fashion you are, in your own mind, Kate Moss, Beyoncé, Kim Gordon, or the ladies from Bananarama. You’re just a better, more attractive alternative of yourself. I gave myself a smoky eye before I slipped on my blue booties and fake gold bangles. “Babe, you look great,” my husband told me. But I didn’t need him to tell me this. I already knew.
If my Jewish grandmother saw me wearing the dress, she would have called it a rag or she would have used the preferred yiddish term, a “schmatta.” (As in, "Why do you insist on wearing that schmatta?") I have a closet packed with unflattering clothing. Though I love every piece equally, like I love my children equally, my most treasured schmatta is my black sweatshirt-drape, cape-like, knee-length jacket, hooded thingy I wear almost every day. (If you know me in real life, you know this is true, and you’re probably sick of seeing me wearing it.) It works as a light jacket or witch costume while trick-or-treating with my kids. Once, it even passed for a '70s, boho romantic ensemble when I went to the annual Stevie Nicks fan tribute, Night of 1000 Stevies. I used to not understand the importance of unflattering, shapeless, schmatta-like garbs; In my early 20s, I wore unflattering clothes because I had an eating disorder. Even when I was too skinny, I was trying to hide my body with oversized T-shirts and ratty, zip-up hoodies. But there’s a big difference between wearing shapeless clothes out of shame and wearing them with pleasure. The first is to hide what’s underneath. The other is to deconstruct and reject ingrained female cultural expectations of what women are supposed to wear — at least what we’re supposed to want to wear to make us feel good or sexy. Man Repeller founder Leandra Medine, who has created a small empire around the argument for wearing unflattering clothes wrote about a pair of her favorite “bad” jeans: “I can’t tell you exactly why I like [these pants] but I can sharply recall having never really cared for pants that do the things we’re supposed to expect of them: flatten our stomachs, tighten our asses, makes our legs look longer and leaner, yadi ya. Maybe that’s a function of my believing that fashion is not about what’s flattering and vice versa or maybe this is simply a matter of style.” You might not want to wear an unflattering outfit every day of your life — there are times everyone wants to see their waist. Yet, there are plenty of celebrity females who regularly subscribe to purposeful not-so-flattering looks, like Helena Bonham Carter, Solange Knowles or Tilda Swinton, who told Harper's Bazaar that most of her closet consisted of “general Lebanese menswear.". And yes, even Jennifer Aniston did it once. When I bought my giant black caftan, it was a risk. That in itself felt freeing, even though I’m well aware that I’m not going to wear it more than a few times a year. But if you need some inspiration, scroll through South African artist Tony Gum’s Instagram feed and there you’ll find a shapeless, “saggy breast” dress, in which saggy breasts are drawn all over the fabric. Saggy breasts and a saggy dress: Sounds like my kind of outfit.