For Oaklie, success was never something handed to her. It was something she had to build, piece by piece, often with no one else holding it steady. At age 12, Oaklie entered the foster care system. Within months, her school, her routine, and the only life she had known were gone. Over the next six years, she moved through thirteen different placements across multiple states, eventually landing in a group home. When she aged out at 18, she stepped into adulthood without a bank account, a credit score, or a single person to call if things went wrong. What she did have was belief in herself, and a quiet determination to build something better.

Finding the Confidence to Succeed

By 28, Oaklie was a single mother of three, working hard to provide for her family. After overcoming homelessness the summer before, she and her children faced another housing crisis when their lease unexpectedly ended. The timing felt impossible. She had just landed an interview at a dream organization, but her belongings were in storage and she had nothing professional to wear. She needed more than an outfit. She needed her confidence back. That is when she found Dress for Success Triangle. At her image coaching session, she worked alongside her coach, Lorraine, to find a look that felt true to who she was and right for the opportunity ahead of her.

“Thanks to Dress for Success Triangle, I was presentable and my appearance wasn’t distracting. I could focus on landing the job—and I got it!”

Moving Forward with Support

The session was about far more than clothing. It was a reminder that she was prepared, capable, and fully worthy of the opportunity in front of her. Oaklie got the job. She secured a position at When People Work, an organization dedicated to helping veterans and individuals with justice involvement find meaningful employment. It was a full circle moment. The resilience she built throughout her own journey now powers the work she does every day for people navigating life with little support, exactly as she once did. “When you look good, you feel good, especially in your professional life,” she shared. Oaklie is not just growing in her career. She is growing as a mother, and as a living example of what is possible when you refuse to let your circumstances define your ceiling. She wants her children to witness firsthand what it looks like to face hard things with courage and come out the other side stronger.

Her message to other women facing uncertainty is simple: you already have what it takes. Let someone help you show it.