About Dragonfly Boudoir
I was introduced to boudoir in 2015. I'd already been doing headshots and other types of individualized portraiture for a while. Then I met a potential client whose story I'll never forget: She was in her early 30s and was facing a double mastectomy. For various medical reasons, she wasn't a candidate for reconstructive surgery, but she wanted to do a session post-surgery that showed her scars. She wanted to create images that she could share with her daughters to show them that there isn't just one way of defining beauty.
From that moment, I understood the power of this area of photography. It quickly became the most emotionally rewarding work I do. Over the years, I have helped hundreds of people celebrate and honor themselves and their joys and hardships. Boudoir is such an empowering, liberating experience, and it is such an honor for me to be part of each person's journey.
Why "Dragonfly"? For many years my boudoir photography was Oaktown Boudoir. I always wanted to call it Dragonfly Boudoir but this domain wasn't available. When I got my Oakland studio, I decided to embrace the vibe of the town.
But I never let go of the dragonfly idea. Dragonflies are symbols of transformation, love, and health — such core elements of what boudoir is all about. Most importantly, dragonflies were the motif of my wedding, and as our 20th anniversary approached, I looked to see if this domain was finally available, and it was.
The decision to rebrand to what I wanted all along is a perfect example of both dragonflies and boudoir itself: I'm reclaiming that which is most significant as I move forward.
"Like many, this was quite a bit out of my comfort zone, but Cheshire makes it fun and easy. If you're a woman, you may be hesitant about a boudoir shoot with a man behind the camera, but he could not have been more respectful; I felt at ease the entire time. He was able to help me bring out a more confident and sexy side, and the photos look like the very best version of myself."
Katie
The team
Cheshire Isaacs, Owner/Photographer
I've been a full-time freelance photographer and art director since 2013. Before going solo I was the in-house art director/graphic designer for Berkeley Rep and other arts and education nonprofits.
I got into photography as a kid and pursued it as a hobby for many years, but it never occurred to me that it could be my job. After being away from it for more than a decade, I picked it back up again when digital cameras started coming into their own. I relearned everything and started shooting professionally in 2009.In addition to boudoir, I love to shoot headshots, maternity, food, performance, and promotional images.
When I'm not shooting, I'm cooking, reading, playing poker and other games, doing crosswords and other puzzles, building with Lego, hiking, kayaking, traveling, crushing it at karaoke, and other stuff. I live in Emeryville with my wife, our teen, and our cat, Ari (Not Sorry).
Alla Retornaz, Makeup and Hair Artist
Alla is a professional makeup and hair artist based in San Francisco and the Bay Area, with over seven years of experience in the beauty industry. She specializes in bridal, soft glam, and elevated fashion-inspired looks, creating refined, modern beauty that feels effortless and timeless.
As a licensed artist with experience at NY & LA Fashion Week, Alla combines technical precision with a strong artistic vision. Her European aesthetic brings sophistication, balance, and attention to detail to every look she creates.
For Alla, makeup is not about transformation — it’s about enhancement. Her philosophy is centered on highlighting natural beauty, skin that looks radiant and luxurious, and creating harmony in every feature. Each bride and client receives a personalized approach tailored to their style, personality, and special occasion.
Beyond artistry, Alla understands the emotional importance of life’s milestone moments. As a mother and a woman who values elegance and confidence, she believes beauty should feel empowering, never overwhelming. Her goal is to create an experience that feels calm, elevated, and unforgettable — leaving every client feeling like the most confident version of herself
The studio
A versatile place to make unforgettable images
Clients are always surprised how many different settings we can create in the studio. Between the options in the main room, the spiral staircase in the back, and the loft — plus lighting and some studio magic — I've counted 25 completely distinct looks, and I'm probably under-counting — and always open to discovering more.
Located in Oakland's Ivy Hill neighborhood near Lake Merritt, the studio is easy to get to, and parking nearby is always available, plus it's only a short ride (or not-short walk) from the Lake Merritt BART station.
Want to see how we can use the studio? Click the cover to download my PDF. Got an idea you don't see here? I want to hear about it!