Issa Rae Is Fueling Her Mogul Era With More Me Time

Step into Issa Rae’s shoes for just 24 hours, and you’ll find that the Emmy-and Golden Globe-nominated actress is an early bird who rises before the sun. “I'll usually get in a workout, then I’ll sit in the dark in my office for about 30 minutes, drinking coffee while thinking, journaling, and writing,” she tells me over a Zoom call. “Each morning, I’m grateful for another chance.”

Rae calls this pre-dawn ritual her “me time,” a vital component of her evolution as a modern mogul.

You might recognize Rae from the popular HBO comedy series Insecure, which she starred in, wrote, and produced. If you’re a true Rae ride-or-die, you’ve followed her journey since she launched Dorm Diaries and Awkward Black Girl, two viral YouTube web series that helped kickstart her entrepreneurial career.

Since those early days, Rae has produced over a handful of binge-worthy projects showcasing her humor and relatable millennial voice, but her influence extends far beyond Hollywood. Her diverse portfolio includes running her independent production company, Hoorae Media, managing talent through her firm, ColorCreative, and facilitating an audio platform, Raedio. She has made her mark in the beverage industry with her prosecco company, Viarae, co-owns the haircare brand Sienna Naturals, and invests in the Los Angeles-based café chain Hilltop Coffee + Kitchen.

If you thought Rae’s multi-hyphenate title couldn’t get any longer, think again. Last year, she made strides in the footwear industry by becoming a global ambassador for the luxury shoe brand Stuart Weitzman. Now, Rae is the influential face of the fashion house’s Spring 2025 campaign.

The collection features a curated assortment of warm-weather shoes, like Stuart Weitzman’s new NudistWrap 50 Sandals, designed with a wraparound ankle strap and a sculptural heel. Other breezy silhouettes include the brand’s Thea Loafers woven with lustrous leather fabric and Power Slingbacks adorned with embroidered florals.

While they're known best for their bread and butter footwear, Stuart Weitzman’s Spring 2025 lineup also boasts the label's first-ever series of sunglasses, including butterfly shades trimmed in metal and rectangular options crafted with two-toned designs. “These sunglasses make me feel fabulous, and I’m really glad that Stuart Weitzman is offering this new category,” says Rae.

Rae tells me that making time for relaxation is the key ingredient to seeking serenity amidst her swamped schedule. The Spring 2025 campaign and accompanying short film, titled “Been ‘Writing’ All Month,” captures the various stages of her creative process—including balance. “I’m always in search of it,” Rae explains. In one scene, she’s thumbing through a script; in another, she's lounging by the pool while embracing a c'est la vie attitude.

Ahead, the actress talks about prioritizing her well-being and navigating her mogul era. She also reveals her signature outfit formula, her fashion icons, and her style glow-up.

When you’re not filming on set or deep in your next business venture, how do you carve out time for yourself to relax and unwind?

Oh, I've gotten so much better about doing that and finding spaces where I can escape the chaos. I just came back from Paris from a writing trip, but it was also nice to be in a different time zone where I could only take meetings at certain times. I’d take walks in the morning to get the creative juices flowing, and I've become really good about scheduling those moments in my calendar in advance so that people know this is my time.

How has balance across your personal and professional life contributed to your achievements?

More recently, and by recent, I mean in the last couple of years, I've gotten really good at regimenting my days and sticking to it. Meetings are such a time suck, but obviously, they're important. But if I had a meeting every day, I’d never [have time to] be creative. So, I’ve started scheduling meetings every other day, keeping the other days clear for creativity. That’s been a game changer for me, and it helps maintain my sanity.

The right shoes can also help create balance. How have they transformed your confidence and style at work?

I'm five-nine, and I feel like I have a short personality, but whenever I wear a great shoe, like a heel, I feel different. Honestly, I feel transformed—ultra-feminine and womanly. Stuart Weitzman is my Hollywood shoe of choice, and when I step onto a red carpet wearing their Nudist shoe, I feel like I’m equipped for this environment.

But if I’m at home or in my office at work, I have to wear a flat. And if I’m on set, it's flats all day—I need to be able to run around and give a note.

Do sunglasses play a role in your personal style?

Sunglasses are my uniform—especially when I want to skip makeup and step out with a bare face but still feel fabulous. As a people watcher, I also get to observe things behind the sunglasses and gather material for whatever I’m writing or creating next.

People are in their zone in sunglasses—especially if you're wearing them inside, which I’ll do in a heartbeat. I actually do a lot of my work in sunglasses—sometimes, I’ll even write while I have them on. They're fitting for my mogul era.

With a busy schedule, do you have a signature outfit formula that helps you streamline the day and feel your best?

I prefer stress-free outfits. When I'm in creative mode, I don’t like to think too much about what I’m wearing, so I’m very much into jeans and T-shirts. I have a slew of these form-fitting, long-sleeve shirts that I can wear with any jeans, so I don’t have to think about it while I’m out for the day.

I've gotten better at knowing what works for me—what looks good on my body type and what makes me feel most confident. It all goes hand in hand. Feeling good makes me more inclined to take risks and, you know, play around with my style because that’s part of the fun.

Fashion is about how you present yourself to the world, so I ask myself that question every day. I want that to be reflected and to feel confident in who I am.

How has your style evolved since you first started in the industry?

It's gone from awkward and insecure to more confident. I used to quite literally run and buy whatever was on sale at Ross before shooting Awkward Black Girl. Aside from thinking about the character, I didn’t put much thought into the clothes [from a fashion standpoint].

Then, with Insecure, it was more about refining my style—this is on HBO, after all. I still wanted to stay true to the character, but I wanted the wardrobe to feel elevated. So, even if she’s insecure, there’s still a flyness to how her clothes present her. That shift has helped me understand my own style and embrace it.

Are there any style icons—past or present—that you draw inspiration from?

I always look to Tracee Ellis Ross because she loves fashion so much, has lived through so many eras, and is also really generous about sharing her knowledge. She's always fabulous. Diahann Carroll—she’s just elegant. When I want to envision who I could be when I’m embracing my most feminine wiles, I think about her.

Shop Stuart Weitzman's Spring 2025 Collection

The rest of Stuart Weitzman's Spring 2025 collection is now available online and in stores.