Another edition of Maria Pinto’s Spotlight Series, In Her Own Words, is here. Each month, we feature the dynamic, stylish, and powerful women who inspire us daily.
This month’s spotlight features Dorothy Capers, Chief Legal Officer and Corporate Secretary for the largest freight brokerage and logistics company in North America.
SHOP EARLY AT THE BOUTIQUE: Luz Coat - Mavi | Millicent Pant - Oxblood
What was your path to getting where you are today?
My path has been shaped by nearly four decades of learning, service, and leadership across different parts of the legal profession. Now in my 39th year of practice, I have had the privilege of serving in government with the State of Illinois and the City of Chicago, practicing in a private law firm, and working as an in-house attorney representing the interests of private and Fortune 500 companies. Each chapter taught me something different—how to serve the public, how to advocate with discipline and judgment, and how to help businesses navigate complexity with integrity. Over time, those experiences have deepened my belief that the law is not just about providing answers; it is about helping people and organizations make thoughtful decisions, solve problems, and move forward with confidence.
What are some challenges you've faced in your job or in your life, and how have you tackled them?
I have faced the same challenge many women face: building a demanding career while also carrying a full life. I am a full-time mother of two daughters, I helped care for two aging parents, I supported my family as we ran a family business, and I made geographic moves for professional opportunities. None of those responsibilities came with a pause button for my career, and my career did not pause for life.
What helped me tackle those seasons was being very clear about my priorities, trying to ask for help when I needed it, and giving myself permission not to do everything perfectly all at once. I have tried to be disciplined with my time, intentional about my choices, and honest about what mattered most in any given season. Professionally, I have also had to navigate different industries, leadership teams, and business challenges, often as one of few women—and certainly one of few Black women—in the room. I tackled that by staying prepared, leading with integrity, building trusted relationships, and remembering that I did not have to shrink myself to be effective. In a largely male dominated profession, it's important that you are seen and heard as a credible business partner.
What are some challenges you're facing right now in your job or life, and how are you tackling them?
With a very fast paced legal landscape and geopolitical forces in play, this has been one of the most challenging seasons in the profession in my opinion. New laws, new executive orders, and new directives are coming out almost hourly and the challenge is keeping up with them, understanding how they impact our business, and keeping a calm focus.
What hobbies, organizations, or philanthropies are you involved in?
Food access and quality food sources are very important to me. I am a chef as well as an attorney, and I have always believed that food is a common thread that brings people together. Around a table, relationships are created, conflicts can soften, and space opens up for real dialogue and connection.
I care about efforts that help people and communities have better access to fresh, quality food and the opportunity to gather, connect, and be cared for through food.
Outside of work, cooking is one of my greatest joys. It allows me to be creative, to serve others, and to bring family together. My love language is seeing my friends and family enjoy what I have created.
SHOP EARLY AT THE BOUTIQUE: Pinar Jacket - Ankara Print | Alex 2 Skirt - Ankara Print
How do you create a work-life balance for yourself?
I don’t know that there is ever a balance—seriously—but over the years I have allowed myself to not have to seek perfection but ensure that for that day, week, etc., I take time for myself, I give to my friends/family, I work hard and do all I can for community in some way—even the smallest gesture of helping an unhoused person or paying it forward in the Starbucks line! That kind of engagement with my community brings me joy when it helps someone else.
What do you love and/or appreciate about being a woman? What is one of the biggest challenges? What brings you joy?
I love the strength, complexity, and range of being a woman. We are often asked to be many things at once—leaders, nurturers, problem-solvers, caregivers, truth-tellers, and steady hands in the middle of change. What I appreciate most is the resilience and intuition women bring to every room we enter. We know how to read a room, hold space for others, make hard decisions, and still lead with empathy.
One of the biggest challenges is that women are still too often expected to prove what should already be assumed—that we are capable, strategic, prepared, and worthy of being heard. For women of color, that challenge can be even more layered. I have learned that I do not need to shrink, soften, or over-explain who I am to be effective. I can be my authentic self and lead with both strength and grace.
How are you dressing right now?
Frankly, as I have moved into my 60s, I feel more comfortable in my skin and freer to express my style transparently without worrying about what anyone else thinks. I am drawn to good, solid style—pieces that are well-made, timeless, and confident—but I also like a little sexy and something unexpected. I love a piece that has personality, whether it is an interesting cut, texture, color, or detail that becomes a conversation piece.
How are you dressing for work?
I still dress for the office, so I would say I am pretty professional in my dress about 90 percent of the time. I am often in executive, board, or business settings where I want to look polished, credible, and prepared. But professional does not have to mean boring. I like to bring my own personality into my work style through an interesting jacket, a great dress, a bold color, a distinctive piece of jewelry, or a silhouette that feels modern and confident.
What is important to you when it comes to buying clothing?
I travel a lot, so I am very practical about what I buy. First, I want pieces that pack well, do not wrinkle easily, and can be worn more than one way. I love clothing that looks polished but does not require a lot of fuss—something I can pull out of a suitcase, put on, and still feel put together. Ease of care matters to me, and so does comfort, but I also want the piece to have some style and personality. If it is versatile, easy to maintain, comfortable, and still feels like me, then it is a winner.
SHOP THE LOOK: Hariko Top - Denim 24 | Mura Blouse - Midnight | Estrela Jean - Denim 24
What are some of your style or fashion icons?
Michelle Obama, Oprah Winfrey, Sarah Jessica Parker, Kerry Washington, and a great friend of mine Jean who slays it every time.
What are some of your favorite features of the Maria Pinto collection?
I love that it is machine-washable, versatile, and so funky! Maria has such a great vision for her collection. The majority of my closet is Maria’s pieces because they are timeless and so easy to style. Her lines are clean which also enables you to alter easily—I lost weight over the years and it has been easy to adjust the pieces for fit. Every time I wear a Maria Pinto piece someone asks “who is that designer?”
What are you watching, reading, and/or listening to right now?
I’m reading a book called Move. Think. Rest. by Natalie Nixon. Great book about the power of taking time to be still in order to be more innovative and creative. My favorite show right now is Your Friends & Neighbors starring Jon Hamm. I love him! We could be friends!
How do you take care of yourself?
I walk almost every day, at least 3-4 miles. My favorite workout lately is a hot yoga and weights class—30 minutes of yoga followed by 30 minutes of weights. It gives me the best of both! I’m working on getting more sleep, but that still is a struggle!
If you could live anywhere (and money is no object), where would you choose?
Capetown, South Africa. I visited there a year ago and I fell in love! Runner up is Nice in the south of France. Absolutely beautiful.
Best gift you've ever received?
So hard to answer because I have a lot of material gifts that are amazing, but the best gifts are my girls, Mariah and Mackenzie. They are my heart and soul. I pinch myself whenever I’m with them as a reminder of how lucky I am.
Best piece of advice you've ever received? What wisdom would you tell your younger self?
Someone once told me “make no unnecessary enemies,” and that advice has stayed with me. There are always moments when people disappoint you, respond poorly, or say something disrespectful. In those moments, I try to remind myself that I get to decide whether it deserves my energy. Some things need to be addressed directly, but not everything needs to become a battle. Sometimes the wiser choice is to step back, look at the bigger picture, and remember that everyone has bad days. That advice has helped me protect my peace, lead with perspective, and save my energy for the things that truly matter.
All looks styled with jewelry available in our Chicago Boutique.
Photo Credit: Special thanks to Ana Miyares for the stunning photography.