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Helping San Diego Teens Dress for Opportunity

July 27, 2026

two teens and a volunteer stand in front of a dressing room entrance at Kohl's during a Dream with STEAM shopping event

When you think about preparing teenagers for their future careers, you probably picture resume workshops, career exploration, job shadowing, or college applications. Those experiences are a core part of United Way of San Diego County’s (UWSD’s) Dream with STEAM summer career exploration program. Still, there’s another important piece of career readiness that’s often overlooked: professional clothing. 

For many high school students, what they wear to a networking event, internship, interview, or their first day on the job can have a real impact on how confident they feel walking through the door. 

Looking the part doesn’t guarantee success, but it can help students feel like they belong and make a strong first impression. 

That’s why every summer, one of the most meaningful experiences with our Dream with STEAM program happens outside of the classroom or business site visit. 

It happens during a shopping trip, where students are paired with caring volunteers to find professional outfits, build confidence, and discover that they’re ready for whatever comes next.

Confidence Creates a Sense of Belonging 

smiling teen in a collared shirt with the tag still on next to a volunteer during a Dream with STEAM shopping event in San Diego County

Dream with STEAM is the summer career exploration extension of United Way of San Diego County’s STEAM-to-Careers program, serving students from Lincoln High School and Escondido High School. Throughout the summer, students explore careers across science, technology, engineering, arts, and mathematics (STEAM), visit local employers, meet professionals, and build the skills they’ll need for college and future careers. 

As part of that journey, students also participate in a shopping event designed to prepare them for what’s next. 

With the help of dedicated volunteers, each student is given a shopping stipend donated by generous donors and corporate partners and paired with someone who helps them select clothing that fits well, reflects their personality, and prepares them for interviews, networking opportunities, internships, and other professional experiences. 

At first glance, it’s about finding the right professional outfit. 

But it’s really about helping students see themselves as someone who belongs in those spaces. 

It’s About More Than Looking Professional

Confidence isn’t something you can hand someone, or that magically appears overnight—it’s cultivated by creating opportunities, removing barriers, and empowering people to discover their own potential.

For many Dream with STEAM students, this shopping experience is the first time they’ve owned professional clothing. It’s an opportunity to ask questions, receive encouragement, and imagine themselves stepping into careers they may never have considered just a few months earlier. 

The experience reinforces an important message: 

You belong here. 

When students can focus on introducing themselves, sharing their ideas, and building relationships, instead of worrying whether they look professional, they’re better positioned to make the most of every opportunity that comes their way.

Volunteers Help Make the Experience Special 

Female teen and a volunteer smiling next to a shopping cart of clothing during a Dream with STEAM shopping event

The clothing is important because of the message it conveys in a professional environment. 

However, the conversations are what students often remember. Reflecting on the day, one student from Lincoln High School shared,

“

I would rate the event 10/10. My takeaway after talking to my volunteer was to never settle, and that there is also something more than you can aspire to do in life.

Student, Lincoln High School


Volunteers don’t need a background in fashion or career coaching. They bring their time, encouragement, and willingness to help a young person feel seen and supported. 

Throughout the shopping experience, something special happens: small mentoring moments naturally unfold. As volunteers and students browse the racks together, conversations shift from finding the right blazer or pair of shoes to talking about college, career goals, and the future. 

One student, Nelly, dreams of becoming an aerospace engineer. She was paired with Sherry, a volunteer who works at Solar Turbines. What started as a shopping trip quickly became an opportunity for Nelly to ask questions, hear about Sherry’s career journey, and connect with someone working in a technical field she aspires to join. It’s the kind of meaningful connection that can leave a lasting impression. 

Those moments happen throughout the event. Whether it’s sharing career advice and insight, exposing them to professional opportunities, offering encouragement before an upcoming internship, or simply reminding a student that they belong in professional spaces, volunteers help build confidence that extends far beyond a new outfit. 

For many volunteers, the experience is just as meaningful. They get to witness students’ excitement firsthand and play a small but important role in helping them prepare for whatever comes next.

A Community That Invests in the Next Generation

Teen from the Dream with STEAM program standing on a green screen stage at KPBS studio in San Diego

The professional shopping event is one part of United Way of San Diego County’s broader commitment to helping local students build a future of long-term financial security. 

Through Dream with STEAM, students from Lincoln High School and Escondido High School explore careers they may have never considered through company visits, mentorship, career readiness workshops, financial education training sessions, and hands-on learning experiences. They build resumes and LinkedIn profiles, strengthen interview skills, expand their professional networks, and begin to see themselves pursuing careers that offer stability, growth, and opportunity. 

Just as importantly, the program helps students develop the financial skills they’ll need to succeed beyond the classroom. Participants receive financial literacy education and open their first bank account, where they receive the education award they earn for completing the summer program. These experiences introduce students to responsible money management while giving them practical tools they can use as they begin earning, saving, and planning for their futures. 

Together, these experiences reflect United Way of San Diego County’s belief that creating lasting financial security begins long before a person’s first full-time job. In a region where the cost of living continues to outpace wages, preparing young people with the knowledge, skills, and confidence to make informed financial decisions isn’t just beneficial; it’s essential. 

Today’s students will inherit an economy where navigating the costs of housing, higher education, transportation, and everyday necessities will require greater financial capability than ever before. By investing early in education, career exploration, financial capability, and self-confidence, we’re helping young people build the foundation to earn, save, and plan for their futures while avoiding barriers that can limit economic opportunity. 

This work extends far beyond individual success. Financial capability creates stronger families, more resilient communities, and a healthier regional economy. When young people are equipped to achieve financial stability, they are better positioned to build wealth, support future generations, and contribute to a stronger, more prosperous San Diego for years to come. 

The professional shopping experience is a stepping stone. It helps students walk into interviews, networking events, and internships feeling prepared—not just because they have the right outfit, but because they’ve gained the knowledge, support, and confidence to take the next step toward their goals.

Help the Next Class of Students Dream Bigger

Support a Dream with STEAM Professional Shopping Event 

Every year, volunteers and sponsors help transform an ordinary shopping trip into an experience students remember long after summer ends. 

If you’re looking for a meaningful way to invest just a few hours in the next generation, we’d love to have you join us as a volunteer or sponsor for the next Dream with STEAM shopping event. Join our email list and be among the first to hear when registration opens for the next event.


Whether you’re helping a student find a blazer that fits, offering encouragement, or simply celebrating their excitement as they see themselves in a new light, you’ll be helping build confidence that extends far beyond a single outfit. 

Other Ways To Support Our STEAM Programs in San Diego County

Each year, volunteers, donors, educators, and business partners help Dream with STEAM students gain the experiences, skills, and confidence they need to thrive after high school. Whether it’s introducing students to new career paths, sharing professional advice, providing financial support, or helping a teen find an outfit that makes them feel ready for their future, every contribution helps open doors. 

By investing in students today, we’re investing in a stronger San Diego tomorrow. As more young people gain access to education, career opportunities, financial literacy, and meaningful mentorship, they’re better equipped to build lasting financial security for themselves and their families. 

That kind of opportunity doesn’t just change one life; it creates a ripple effect that can strengthen our communities for generations. 

If you’d like to be part of that impact, there are many ways to get involved. In addition to volunteering at a future shopping event, you can partner with United Way of San Diego County to provide career exploration opportunities or support the program through a donation. 

When more students have the opportunity to succeed, our entire region benefits. Together, we can help build a San Diego County where every young person has the chance to achieve financial stability, pursue their dreams, and contribute to a community where everyone has the opportunity to thrive. 

  • Learn more about Dream with STEAM and STEAM-to-Careers (and how you can get involved) at uwsd.org/steam-to-careers. 
  • Partner with us on programming for students or host students at your company. Contact our team at: https://uwsd.org/community-partnerships/ 
  • Follow us on social media to see us in action throughout the community.
  • Sign up for our newsletter below to stay updated on our latest initiatives. 
  • Make a gift today to support our work and programs.
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