High Road Academy of Prince George’s County Seniors Dress for Success

Dress for Success at High Road Academy of Prince George’s County
Seniors at the High Road Academy of Prince George’s County are preparing for life after graduation through the school’s “Dress for Success” initiative. The program builds confidence and professionalism and teaches practical life skills.
Randi Tyree, who has worked in the school’s transition program since 2011, helped bring Dress for Success to life after recognizing that students needed more preparation for life after High Road. Yolanda Whitehead, who has served in the transition department for the past four years, now co-leads the initiative.
How the Dress for Success Program Prepares Students
A longstanding program at the school, Dress for Success, teaches students that professional presentation goes deeper than looks. Participants learn to build a professional wardrobe, maintain personal hygiene, strengthen communication skills, prepare for interviews, and practice workplace etiquette. They also learn how to engage with peers and supervisors in a professional setting.
Preparing Seniors for Professional Success
While the program officially kicked off in December, preparation began in October with early conversations and field trips. Seniors started by identifying their clothing sizes and style preferences while discussing workplace expectations. From there, each student was tasked with assembling a complete professional outfit.
With staff guidance, students visited Macy’s, Burlington, and local thrift stores to find appropriate pieces, exploring a variety of retail options to accommodate different price points and resources while building the confidence to put a complete look together.
Students Build Confidence Through Dress for Success
For senior Daniel Davis, the Macy’s trip was eye-opening. He shared that the experience helped him identify what he needed, even if some items did not fit as expected.
“Now, I feel better about myself,” said Davis. “I don’t always feel comfortable, but I get more comfortable every day presenting myself professionally.”
Weekly Practice Builds Professional Habits
Every Thursday, students wear professional attire to school and meet in the transition lounge. Together, they review a rubric that evaluates clothing choices – including belts, socks, and shoes – as well as personal hygiene, facial hair, and jewelry. The weekly evaluations motivate many students, including senior Nia Lattimore.
“Every time I dress for success, I know I’m putting myself out there,” she said. “When I get good scoring, it makes me feel like I’m doing a good job … and then I realize I am doing a good job.”
The group also engages in meaningful discussions about first impressions, workplace expectations, and how to balance authenticity with professionalism.
Peer Feedback Strengthens the Dress for Success Program
Peer feedback is a key component of the program as seniors offer their kudos to one another and provide constructive suggestions for improvement. After one evaluation, Davis’s peers suggested that he add dress shoes to finish his outfit. He took their advice and noticed immediately that he felt even more confident.
“Everything is a teachable moment,” said Tyree. “The students working together, they are always going to take the feedback, and they are more likely to listen to their peers. They hold them more accountable when involved in the grading.”
Whitehead echoed that sentiment, noting how students’ attitudes evolve over time.
“There are always a few who feel reluctant in the beginning,” said Whitehead. “Then they get excited. They receive positive attention, and once they see the bigger picture, they understand the why.”
The Impact of Dress for Success on Students
The program’s impact became especially clear during a school-wide pajama day. To Whitehead’s surprise, several seniors chose to wear their professional attire instead.
Lattimore, whose goal is to become a veterinarian, said she wouldn’t change anything about Dress for Success. “It helps you get ready for the real world, and I really appreciate that.”

