How I Work with My Stylist as a Busy CEO (hacks for power dressing)

When I was growing up, my family didn’t have a lot of resources. We shopped at the $.99 store, Conway, Danice, and—if I was lucky—Rainbow. But one thing I have always loved, and maybe it’s because I am a Leo rising, is a statement piece that stands out. I would ask my mom for an orange coat or orange sneakers, always gravitating toward the most colorful items. Sometimes people would tell me I looked like a bag of Skittles (I don't think they meant that as a compliment, but I took it as one)! It was busy and sometimes distracting, but I knew I had a point of view.

I got my inspiration from two incredible women. First was my great-grandmother, Willie Mae. She was the type of woman who would put an outfit together no matter where she was going—even just around the house, she would wear nice dresses with pleats. When we went out, she would wear pretty suits, have her hair perfectly done or put on a cute wig, wear gloves, and sometimes finish it off with a very fabulous hat. My mother was the same way. As we started to grow more financially stable, she would buy Tahari suits from Macy’s to wear for the hospitality unit at church. She was always so elegant and had the best accessories that brought her outfits to life. I saw style all around me and always knew I was cute.

Finding My "C-Suite Swag"

As I got older, I realized that whenever I walked into stores, salespeople would tell me, "Oh, this looks really good on you!" no matter what I put on. I had to learn to discern between the outside noise and picking things I really liked. People will always try to sell you something, but it may not fit your personality. Early on, I knew my choices had to be authentic to me.

As I was growing my corporate career, I was such a fan of fashion that I started a Tumblr blog called CSuiteswag.com. I wrote about the link between how we dress, the music we listen to, and how it all puts us in the right mindset for opportunities at work. It was really about the swag that’s required in the C-suite. But despite my love for clothes, I lacked a real knowledge of how items worked together. I would pick things I loved and that fit well, but sometimes I felt like those choices just weren't moving the needle. I felt safe. I felt boring.

Life also threw curveballs. While going through a divorce, my weight fluctuated, and I gained about 30 pounds. I didn’t necessarily want to commit to that size, so instead of doing a lot of shopping for clothes I’d be stuck with, I used Rent the Runway to borrow items. It was a great bridge, but I knew I was ready for a true elevation when I got to a consistent size & started buying items I knew I could reinvent for years to come.

The Stylist Intervention: Making Room for the Statement

I was drawn to this amazing woman at an event, and we quickly became friends. She was a stylist, and I asked her to style me pretty much as soon as we met, but she avoided the topic for a bit because of our budding friendship. She was hesitant to work with friends, so I waited patiently.  

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In the meantime, I worked with another stylist who helped me update some of my choices. She showed me how color combinations can really make you pop and introduced me to basics I wouldn't have thought of, like silk pants, adding more textures & really nice flowy jackets.

Still, I was craving true innovation in my style and approach.  I wanted what Law was doing for Zendaya. When that contract ended, I went back to my friend Erika and pushed her again. She finally said yes! She came over to my house, went through my closet, and while she was delighted by my eccentric eye, she gave it to me straight: everything in my closet was a statement piece. "You cannot have a whole closet of statement pieces," she told me. "You still need more basics so that the statements actually have room to make a statement."

She instructed me to buy the basics. (There is a brilliant 1936 quote from Elsa Schiaparelli that I saw at the Victoria & Albert Museum Schiaparelli exhibit in London about the basics women need in their closets, and it perfectly mirrored Erika s advice). 

Because I genuinely enjoy shopping and have built relationships with personal shoppers at places like FWRD, Farfetch, and Bergdorf Goodman, I continued to do my own shopping, but with a new focus on those necessary closet staples.

The Blueprint: How We Work Together

As a CEO, my days are incredibly full. I have employees, contractors, and clients to manage and I'm juggling many hats. The stress of having to make decisions on what to wear simply doesn't work with my lifestyle. There’s a reason Mark Zuckerberg maintains a uniform of a hoodie and Steve Jobs wore his black turtleneck. There is an ease that comes with a consistent uniform—it alleviates decision fatigue.

I noticed that whenever I didn’t love how I looked, it was because I felt rushed and didn’t have time to really plan an outfit. Outsourcing these decisions creates a sense of ease, knowing that no matter how chaotic work and life might be, you’re still showing up as your best self.

Here are the exact hacks and processes for how Erika and I collaborate to keep my style elevated:

• Bimonthly Styling Appointments: We have a standing appointment every other month to keep my wardrobe fresh and organized and identify anything I need to sell/donate and gaps I may need to fill.

• The Event List: I keep a running list of all upcoming events and specifically how I want to show up for them so that Erika can come prepared with ideas, down to how my hair and makeup should look.

• Curating the Looks: During our sessions, we go through my closet and curate specific looks for those events, plus a couple of go-to looks for day-to-day wear.

• Upgrading the "Off-Duty" Hours: When we first started, I felt confident at events, but my fly wasn't consistent. I was reverting back to sweatpants and t-shirts on the days I didn’t want to put in effort. I told Erika I wanted options for non-events, so we upgraded everything. We talked about how to be fabulous at home with nice pajamas, and we put together cute outfits just for walking my dog. I started to see myself differently in the process.

• Cataloging My Closet; We use the app Indyx to digitally catalog and share my closet. I have about 1000 items uploaded (they make it extremely easy to digitize your wardrobe) and it helps Erika style me remotely when I have an urgent need or when we can't meet in person. She sends me lookbooks with items I already own. Consistently, after I shop for new items, I let her know what's updated via the app.

  

  

  

  

• On-Site Support: If I have a really big event, like a photoshoot or Paris Fashion Week, Erika joins me to make sure that everything is laying correctly and even has done quick fixes (like safety pinning a hem or taping my chest in place). It makes a huge difference.

• Collaborative Feedback: I still do all my own shopping, and she’s always pleasantly surprised by what I pick up. She gives me a perspective on how to put it all together that I could’ve never imagined. When I try styling on my own, she gives me honest feedback on when I’ve hit the nail on the head and when it needs work.

• Integrating My Values: Erika knows that I value things like shopping from queer and minority owned brands (e.g. Harbison, Sergio Hudson, Alexis Bittar, BruceGlen) and is always finding ways to bring that to the forefront. She introduces me to cool brand collaborations and is always sharing a new brand to put on my radar. We also value sustainability and focus a lot on shopping less and reworking things that are already in my closet. I wear the same items over and over again, but always in a fresh new way. It’s a really fun challenge!

  
  

Here are some of my favorite looks that we created together:

The Secret Weapon: It's Not Just About the Clothes

As my mentee Isaiah recently reminded me - Deion Sanders famously said, "If you look good, you feel good. If you feel good, you play good. If you play good, they pay good." How we feel about ourselves definitely plays a role in our performance and inevitably, the results we get.

But there is one final piece of the puzzle that Erika put me onto when it comes to power dressing: understanding the fit of the garments. We see celebrities on red carpets looking flawless, but they are not just buying clothes off the rack and putting them on. In fact, clothes off the rack—whether mass-market or haute couture—rarely look good without editing them to the body.

Erika introduced me to Sylvio Kovacic, a dressmaker for the stars who works with clients like Sabrina Carpenter, Jennifer Lopez, and Mariah Carey. He is in incredibly high demand and will not just take on any client. This is where the benefit of treating people well and building real relationships comes into play. Erika met him through her styling work years ago, and because I was her friend—and because Sylvio and I built a genuine relationship of our own—he let me in.

Working with him has upgraded my whole closet. He has taken gowns I bought at a deep discount and reconstructed them to make them look like they just came off a runway. That alone has had a huge impact on the elevation of my style.

Ultimately, working with a good stylist isn’t just about their ability to style and be innovative. It’s about the network they bring, the relationships they carry, and the confidence they help you build from the C-Suite to the living room. But more than anything, you have to remember that having your own fly is an inside job more than an outside job. All the stylists and tailors in the world can't wear the clothes for you. You have to put them on, look in the mirror, and just know you're that girl.

Here is Erika's link if you want to work with her.