it’s time to be you.

An unhurried day, tailored just for you, where you can finally express who you are under the surface. An experience like none other that will give you a lifetime of memories. So much more than beautiful images, boudoir can transform how you see yourself and how you love yourself. Even if you got here because you're creating a gift for someone else, this will be one of the best gifts you can give yourself.

hi, my name is...

A quick intro from me — got 98 seconds?

that’s what they said

  • "From the first email to the final shots, Cheshire was kind, supportive, and helpful. He did a great job helping me prepare for the shoot so by the time I walked in, I felt completely ready and excited. Cheshire clearly loves what he does; the whole experience felt natural and fun. Now I have gorgeous shots that I feel really capture me. I cannot recommend Oaktown Boudoir enough!"
    Kate
  • "I wasn’t expecting to have so much fun! Posing, laughing, and getting in touch with my come-hither side was exactly what I needed. Cheshire is so easy to be with. He makes the whole experience feel quite natural and fun. Words failed me for quite a while when I saw the pictures. I didn’t realize how much I needed this transformative experience. I have so many levels of gratitude and joy in this experience."
    Serene
  • "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
  • "Cheshire was incredibly gracious and meticulous and made me feel incredibly comfortable throughout. He takes care to understand your comfort level as well as preferences, and easily pivots to tailor the experience to you. Best of all, he treated me as a collaborator and encouraged that I bring my own vision and ideas, which added a fun artistic dimension to it. The experience was absolutely wonderful!"
    Rita
  • "As a blind person I wasn't really sure about what my options were. Cheshire took all the time to really explain things and figure out how to make things as accessible to me as possible. He sent me some sneak peaks of images after the shoot with very detailed image descriptions as well which I certainly wasn't expecting but it made a huge difference to me and really shows his dedication to his individual clients. Thank you to everyone else who gave so many good reviews because it made choosing Cheshire an easy choice."
    Tiffany
  • "I cannot overstate how amazing the whole experience was. Cheshire was enthusiastic about my ideas, and really worked with me to make aspects of the shoot very customized to me and my partner. Bring your weirdest ideas, and he'll make them absolutely beautiful. If you've ever thought about doing a boudoir shoot, you should ABSOLUTELY take the plunge and do it! You'll be in the best hands with Cheshire."
    Emily
  • "Cheshire was very kind to me all the way through. He gave me a tour of his studio, listened to my story, and assured me he will take care of the rest. What I like and admire him the most is he made me feel safe and secure throughout everything. Overall, my experience for my very first boudoir photoshoot with Cheshire was amazing and life-changing!"
    Melissa
  • "I cannot say enough about how incredible my experience was with Cheshire! I was excited but hesitant to do a boudoir shoot, but Cheshire made me feel comfortable from our first interaction. He was so professional and thoughtful when we were in the planning stages and helped me come up with the kind of shots I was envisioning and the vibe I was trying to achieve. The whole experience was seriously amazing!"
    Kendall
  • "What an amazing experience. I have several friends that have booked with him so I knew I was in good hands. I’m not a shy person but his cool gentle demeanor really had me relaxed and confident in our session. I was amazed how great the pics came out in just a short time. My fiancé was pleasantly surprised with his Xmas gift and I owe it all to this amazing experience."
    Jennifer
  • "This was such a fun experience. Cheshire made me feel so comfortable and we had lots of laughs. His work is absolutely beautiful and he made me see my own beauty. I gave the photo book to my husband as a wedding gift and he LOVES it. Everyone should have the experience of a boudoir photoshoot. Thank you so so so much!!!"
    Marissa
  • "We loved working with Cheshire, from first contact to the photo shoot itself! He's so thoughtful, both in the physical details of the space he so lovingly provides, and, just as importantly, how he deals with us as people. He made us feel more than comfortable and the photos, ultimately, were superb! Can't wait to head back into his studio and work with him again."
    Girish
  • "I had the best day creating photos for my fiancé as a surprise wedding gift. I was apprehensive at first but Cheshire made the whole experience feel so natural and fun. I was amazed by what I was capable of and how the photos turned out. He is an all star and you won’t regret choosing him!"
    Kylie
  • "Cheshire absolutely made my vision come true, made me feel comfortable, and went above and beyond spending time to make sure I was happy with the pictures he had taken. The direction he provides is super helpful, you can tell he has been doing this for a while! I am so happy I made the decision to do this photoshoot with Cheshire (my husband is ecstatic about it too!)"
    Bre

    welcome in.

    Oaktown Boudoir is an inclusive space. I work with solo clients, couples, and groups. I am honored to help clients across the spectrums of race/ethnicity, age, gender, sexuality, body type, disability, and more.

    In these pages you'll discover how I craft a one-of-a-kind experience for each client: from detailed one-on-one pre-planning to your luxurious session to meticulous work creating your finished items. As you'll find out, I give an incredible amount of individual attention to each client. (If you missed the testimonials above, scroll back up and see what my clients say about how much I do for them.)

    So that I can give the most care for each client, spots are limited. At most I accept two bookings per week. I hope you'll take one of those for yourself. Ready to find out more? Click the buttons below to learn more about my approach and how I can bring your unique vision to life.

    no time to explore right now?

    Here's everything you need to know in a nutshell. I'm Cheshire Isaacs, a top-rated Bay Area boudoir photographer who specializes in natural boudoir photos. I'm grateful to be included in lists such as 12 Best Boudoir Photographers in San Francisco (Peerspace), Top 10 Boudoir Photographers in San Francisco (BoudoirRule.com), and more. I've been doing boudoir photo shooting since 2015 and have taken care of hundreds of clients since then. Please get in touch with one of the buttons below and let's chat about how to get you your absolutely gorgeous new boudoir pictures.