Cleo Wade Still Takes Style Cues From Her Seventh Grade Self

Seven years ago, Cleo Wade composed her first Instagram post. The photograph she posted was of a note, written in what would become the poet-activist-author’s signature blocky scrawl—it read, “Dearest, I am writing you this letter to inform you of my unbreakable nature. That’s all.” The post, signed “Love, Women everywhere,” marked the beginning of Wade’s rise through the echelons of the Internet to become Instagram’s own “Millennial Oprah,” a voice calling for confidence and connection on a platform that too often fuels self-doubt and isolation. In the years since, the Louisiana native’s bite-size morsels of self-affirming wisdom have earned her some 750K followers, among them a gaggle of celebrity acolytes including director Ava DuVernay and activist Rachel Cargle, and a book deal that led to the publication of her bestselling, mantra-laden volume Heart Talk: Poetic Wisdom for a Better Life.

Now, after years of coaxing her audience onward, Wade has paused to reflect on the path that brought her here—to Los Angeles, to motherhood, to national acclaim. In her latest book, a children’s story titled What the Road Said, Wade illuminates the moments of uncertainty that punctuated her own childhood; “I had to dig into the times when I felt alone, or or scared, or ashamed,” she says. But what began, she says, as “a way of consoling my younger self,” morphed into something completely different when, half-way through the writing process, Wade learned she was pregnant. “All of a sudden it became a love letter to my future child. These are words I want to raise her on, and also words I want to be reminded of as a parent.”

Just months after the birth of her daughter, Wade took a break from celebrating the release of What the Road Said, out today, to look back on her fashion journey, and the lessons she’s gleaned from the clothing she wears.

What is your go-to outfit for a day off?

I am one of those strange people who actually enjoys wearing jeans at home. It started when I began working at home far before the pandemic, because I needed a way to feel like I was still going to work.

Describe your style in three words.

Happy. I never wear anything that doesn’t put me in a good mood. Easy. I hate wearing things that are uncomfortable. And adaptable. I don’t want to be worrying that what I’m wearing is going to rip in the back when I pick up my daughter, or that it won't allow me to sit and write for a couple of hours before going out into the world.

What was the last thing you purchased?

Yesterday, I bought this purple turtleneck from Goop. I’m such a sucker for their emails, they sell me something every single time. The color will just put you in a good mood.

What were you wearing yesterday, and why did you decide to wear it?

It’s hard to remember yesterday, but I think I went to Barnes & Noble to sign copies of my new book. I was wearing one of my partner Simon’s old sweaters, some silky pants and my Vans. I don't know why, but someone else's cashmere always feels softer. I also love to put my hair up into things— I have two bucket hats that I wear all the time, a Prada one and an Isabel Marant one.

What was your style like as a teenager?

To be honest, I never grew out of my seventh grade tomboy phase. Simon says I still dress like a teenage boy. It was—and still is— all backwards Yankee hats, pigtails, my old beat-up Vans and Sambas.

What were the other kids wearing when you were growing up?

A lot of tie-dye and denim overalls. Umbro soccer shorts were a big thing, Wigwam socks and these chunky Adidas that are now back in style. But I grew up in the South, so of course there were a lot of girls wearing Lily Pulitzer, seersucker, that kind of thing.

What's the most prized possession in your closet?

Before having a kid, I would have said, “It’s such a dream to have a Gucci bag in my closet, because I never thought I’d be able to afford that.” But now, the first thing that comes to mind are two old t-shirts from when I was a kid. To be able, one day, to give my daughter something that I wore at her age is really special.

What was your first major fashion purchase?

There was a point in my life, actually just a few years ago, that I went from being a thrift store person to someone who could support designers at full price. I began to appreciate the satisfaction of supporting new talent, and recognizing the value of clothing in the same way as if I were collecting art pieces.

What was the most recent big item you purchased?

I have this chain link necklace from Tiffany that I wear every day. I think the only piece of jewelry I have that is more expensive than it is my engagement ring. It’s a big chunky choker, and every day I’m shook by the quality of it. It’s so beautifully made.

Favorite fashion moment from pop culture?

I live and breathe for every time Daniel Kaluuya gets dressed to give an interview or accept an award. It’s everything I love in a photo. He’s so swaggy, so cool, and chic.

What is always in your bag?

I bring my Akila sunglasses with me everywhere. They have these fun colored lenses that brighten up your day. And, of course, chapstick. I recently splurged on a Chanel lip balm, and I’m blown away. It’s completely worth the hype.

Who’s your ultimate style icon?

100% Shiona Turini—I always joke with her that I’m her friend, but I’m her fan first and foremost. We work together, so I hope her genius is rubbing off on me.

Where are your favorite places to shop?

Since I moved to L.A., I have no idea where to shop. But every time I go to Rachel Comey I feel so relaxed. Everything is effortless there. I visited her shop after lockdown rules eased up, and it was like a breath of fresh air.

What is currently on your shopping wishlist?

This William Okpo set—they match the hat with the dress with the bag in a way I’ll never be able to pull off, but I’m going to try. I found it on Black Owned Everything.

Do you have any fashion regrets?

I first started traveling in my late teens, and because I didn’t grow up with money I had this idea in my head that I would only see these places once in my life. So I stuffed my suitcase with, like, 40 kimonos in Japan, I bought every tchotchke in the Moroccan bazaar. There was a period after that when I was so over-accessorized from all my travels that I jingled when I moved, like a cat moving through the house.

What’s your style pet peeve?

Clothing is one of the few things in life that we can actually control. It can prop us up, or brighten up our day. So I think my biggest pet peeve is when people don’t give it the power to do that or turn it into another reason to feel insecure in the world—by complaining about what they’re wearing or being self-deprecating. We just don’t have to do that!