Professional Headshots in Boston & Waltham – Studio or On-Location

When was the last time you updated your headshot?

Whether you're a corporate executive, small business owner, creative professional, or graduating student, your headshot is often the first impression you make. In today’s digital world, a high-quality, authentic headshot is more important than ever—and I’m here to help you make yours stand out.

I’m Cheryl Clegg, a Boston-area photographer specializing in professional headshots, both in-studio and on location. With over two decades of experience working with clients from major corporations to individual entrepreneurs, I know how to create images that look confident, approachable, and polished—without feeling stiff or overproduced.

Headshots in Studio: Controlled, Classic, and Efficient

My Waltham studio offers a clean, well-lit environment where we can control every element—from lighting to background—to create timeless, professional headshots. Studio sessions are ideal for individuals looking for consistent, high-quality portraits for LinkedIn profiles, company websites, speaking engagements, or press features.

Clients love the convenience of the studio, especially when they want a classic headshot with the flexibility to change wardrobe, backdrop, or mood. Plus, you get the benefit of a relaxed, private environment where we can take our time to capture your best angles.

On-Location Headshots: Natural, Personalized, and Dynamic

Prefer a more lifestyle or environmental feel to your headshot? I also travel for on-location sessions—whether it's your office, a downtown Boston backdrop, or a coastal Maine setting. These portraits feel more organic and are perfect for teams who want a cohesive look in their own workspaces or professionals who want something less traditional.

On-location sessions are great for companies needing headshots for multiple employees or brands that want imagery that reflects their unique personality and industry.

Why Choose Cheryl Clegg Photography?

What sets me apart is my ability to put people at ease. I guide my clients through every step—from posing and expression to wardrobe and final selection—so you never feel unsure or uncomfortable. I’m not just taking your photo; I’m helping you tell your story with confidence.

Many of my clients have told me how their new headshots helped them land speaking gigs, get hired faster, or finally feel like their photo truly reflects who they are. That’s why I do what I do.

Ready to Update Your Headshot?

Let’s create something that works for you. Whether you need a quick studio session in Waltham or a full-team shoot at your office, I make the process smooth and professional.

📍 Serving Greater Boston, Cambridge, Waltham, and beyond
📧 Contact Cheryl Today to schedule your session
📸 Visit the Headshot Portfolio to see more