Craig Bailey at Perspective Photo is a Boston portrait specialist who creates natural, flattering professional portraits and headshots. His patient, documentary style reveals authentic character.
Perspective Photo is Craig Bailey’s personal practice for portrait photography in Boston. As a portrait specialist, Craig treats each session as a chance to tell a brief, honest story about the person in front of the camera—because photography, for him, is both capture and reflection. He often describes himself as a griot who carries a camera: an unobtrusive observer whose goal is to reveal the small, truthful gestures that define a subject. Why choose Perspective Photo? Craig combines years of documentary experience with a calm, patient approach that helps even camera-shy clients relax. Rather than staging forced poses, he listens, watches, and waits for real expressions and interactions. The result: professional portraits and headshots that look natural, flattering, and genuinely you—ideal for LinkedIn profiles, business portraits, creative portfolios, and personal branding. What makes his approach special is the balance between technical knowledge and human sensitivity. Craig’s background in event and documentary work means he understands light, timing, and composition, and he pairs that technical skill with a conversational style that puts people at ease. He values authenticity over artifice and aims to capture moments that feel lived-in rather than overly produced. How he works: every portrait session begins with a short conversation about intent—who you are, how you want to be seen, and where the images will be used. From there Craig crafts a relaxed session rhythm, offering gentle direction when needed and encouraging natural movement and expression. Many clients appreciate his patience and steadiness; he creates a low-pressure environment that leads to more honest photographs. Based in Boston and rooted in the city’s neighborhoods, Perspective Photo specializes in on-location portrait work tailored to each client’s needs. Whether you need a polished professional headshot or a character-rich portrait for editorial or personal use, Craig brings a documentary sensibility and a thoughtful, human-first approach to every session.