What I Wear to Work: Deborah Yager Fleming

Deborah Yager Fleming, CEO of Acqualina Resort in Sunny Isles, Florida, can pinpoint the moment she found her calling 30 years ago. Post-graduation, when she landed an entry-level position in a hotel's sales and marketing department in Miami," the world lit up for me," Fleming says. Jumping off of that aha career moment, Fleming went on to work at some of the world's leading hotels, always looking to learn and grow with each new role. 

As CEO and partner of Acqualina, Fleming oversees the resort's executives and managerial staff while working on innovative new programming in the competitive hospitality space. Working in an urban resort, Fleming says her busy days are often longer than the traditional nine-to-five office hours, filled with client meetings that take her from the property grounds to dinner engagements around Miami. Fleming takes a timeless approach to her work wardrobe to keep herself looking polished and says she always feels better overdressing than under-delivering. 

Ahead, we chatted with the CEO about how she gets her day started, the importance of constantly seeking inspiration, and her favorite pieces to help her take the day head-on.

On Her Morning Routine:

I'm usually awake by 7 am and like to start my day with exercise at a local fitness club around three times a week. I'm a big fan of pilates and yoga, and spinning. There's a little more pep in my step, and I ease into the day better. I also have green juice almost every morning before I have my coffee. Then, I usually listen to a podcast on the drive to work. I especially like listening to podcasts that help inspire me. SmartLess, hosted by Jason Bateman and Will Arnett, is excellent. They're so good at connecting with their guests, and I'm interested in hearing how their guests, usually really successful people, got to where they are today.

On Getting Dressed:

Getting dressed seamlessly comes down to an organized closet and sets up a more successful flow for the day. Because I live in Florida, I tend to gravitate towards color, and my closet is color-coded, making it easy for me to walk into my closet and pick something out for the day. If I know I want to wear certain items together, I’ll pair them that way. My days usually take me from a ZOOM or boardroom meeting to an outdoor lunch or seaside meeting, so I like to put together comfortable and effortless outfits, like tea-length dresses that make it easy to walk around the resort. I look for designers that can transition from day to night and investment pieces that will last for more than one season. Some of my go-to designers are Carolina Herrera, Cynthia Rowley, Sandro, and Maje. One of my latest purchases was a red pantsuit from Maje in Acqualina’s signature red color.

On Accessorizing:

I have a thing with shoes—especially when I know I’m going to spend a lot of time outdoors in the sand or grass at the resort. Some of my most comfortable are my Chloé flats, and I love my Rothy’s. I own them in several different colors. I love that they’re made from recycled materials; you can throw them into the washing machine to clean them. I have a lot of respect for that brand.

If I wear a great watch, it gives me a lot of confidence. I was recently presented with a Chopard Alpine Eagle watch alongside an award, which has a lot of sentimental value for me. When I wear it, I not only feel confident, but it reminds me of accomplishments I’ve had along the way.

Shop Deborah's Favorites: