Middlebury Magazine – Editorial Illustration
Capturing the changing meaning of a college reunion through illustration.
For the Summer 2026 issue of Middlebury Magazine, I was commissioned by Pentagram to create an editorial illustration accompanying Alison Osius' essay reflecting on returning to her college reunion. Rather than focusing on nostalgia alone, the article explores how time reshapes our perceptions of both ourselves and the people around us, revealing that many of our assumptions from university years were misplaced.
The challenge was to distil a reflective, text-heavy essay into a single illustration that felt warm, optimistic and full of small discoveries.
Client: Middlebury College (via Pentagram)
Project type: Editorial illustration
Role: Illustrator
Usage: Magazine feature / full-page editorial illustration
Focus: Visual storytelling, narrative composition and character-driven illustration
Brief: Create an editorial illustration to accompany a reflective essay about returning to a college reunion years later. Rather than illustrating one specific moment, the artwork needed to capture the wider emotional journey of reconnecting with old classmates, revisiting shared memories and seeing familiar people through a different lens.
The work needed to:
Feel warm, optimistic and inviting
Bring together multiple moments from the essay into a single cohesive illustration
Encourage readers to discover small visual stories as they explored the artwork
Sit comfortably within the magazine's editorial layout
The story combined multiple conversations, humorous anecdotes, emotional reflections and moments of reconnection across the reunion weekend.
The challenge was to:
Bring many separate moments together without creating visual clutter
Keep each interaction readable while maintaining a strong overall composition
Balance narrative storytelling with clarity and editorial function
I focused on creating a rich, hand-drawn scene that brought together many of the essay's individual moments within a single composition. Rather than illustrating one event, the aim was to capture the atmosphere of the reunion as a whole, allowing readers to discover new conversations, interactions and small details the longer they spent with the artwork.
Instead of reducing the story to a single visual metaphor, I wanted to weave together its humour, reflection and sense of connection into one cohesive illustration that mirrored the experience of the reunion itself.
The finished illustration was published as the opening artwork for the feature in Middlebury Magazine, helping transform a reflective, text-led essay into an engaging visual narrative that draws readers into the story before they've read the first paragraph. The result adds warmth, personality and narrative depth to the editorial design while rewarding closer exploration with layers of small storytelling moments.