Sarasotan Cassandra Pietrantone, a University of Florida senior interning with the Tampa Bay Rays, is a self-proclaimed tomboy. Eventually hoping to work in major-league baseball operations, she’s looking to upgrade her sense of style.

CASSANDRA’S GOAL: “I wanted to find a level of comfort in clothes I normally would not wear and see something different within myself.”

JACKIE’S APPROACH: “Cassandra, who wears khakis and a polo shirt or a Rays uniform at work, would like to have more style, yet be comfortable sitting at her desk or walking the stadium with the grounds crew. I wanted to stay within Cassandra’s sporty-casual style and work that idea into her professional look. I started with a soft, woven-cotton pant in navy as a fresh option to basic black. Then I added a bright orange top as a bold contrast to the navy. I selected a jacket for its great fabric and weight and sporty yet classic stripes. The cut suits Cassandra’s silhouette and hits her in all the right places. Cassandra does a lot of walking in the course of a day, so I finished the outfit with an orange ballet flat for comfort and an additional splash of color. She can wear this outfit with or without the jacket and still be professional.”

CASSANDRA’S TAKE:  “I loved the feeling I got when I put the outfit on. I felt professional yet comfortable. It was fun to see myself in a different color because an orange top would not have been something I would have chosen for myself.”

Where to buy

Blazer, $98, top, $54.50, pant, $79.50, and necklace, $34.50, all from Ann Taylor Loft; Oka b ballet flats, $45, from T. Georgiano’s.

Story and Styling by Jackie Rogers

Hair by Michelle Bell of Fresh Salon and Spa

Make-Up by Brooke Cupp of Fresh Salon and Spa 

Photography by Alex Stafford