ChrisSoFly’s self-portraits celebrate his love for fashion, music, and awakening from rigid gender roles.

Growing up, the Sanford, Florida-based multidisciplinary artist never imagined he’d feel comfortable wearing dresses, wigs, and makeup, and sharing photos of himself with the world. “Once I finally put my own fear of judgment aside and became comfortable in my own skin and started dressing how I wanted and expressing myself freely,” Chris writes, “ I realized that this may be my purpose….showing that boys can be princesses too.”

In his self-portraits, which he shares predominantly on Instagram – often with tens of thousands of likes and hundreds of comments – Chris unapologetically and joyfully confronts the camera with bedazzled glory.
The series started earlier this year when Chris began designing fashion pieces while teaching himself to sew through Youtube videos. His creations manifest themselves as pastel dresses, flowers in his hair, posing before floral backdrops that highlight his exuberance and power. I spoke with Chris to learn more about his experience and work.

I spoke with Chris to learn more about his experience and work.

Jon Feinstein in conversation with ChrisSoFly

Jon Feinstein: Thanks for catching up with me, Chris! I’ve been following your work on Instagram for a few months now and continue to be inspired by you. I’d love to learn more about the origins of your series -- how did it start?

Chris: This series initially started after I took a (much needed) social media hiatus for a few months. I was experiencing a whirlwind of emotions as the Black Lives Matter movement was at its peak and we were all thrust into a quarantine caused by a global pandemic. With multiple devastations occurring simultaneously, I was lost in a state of feeling very uninspired, very hopeless, and actually quite depressed. Once I was finally able to pull myself out of that dark place and kind of bring myself back to life, in a way, I began to slowly start creating again. There was a major shift in my thought process towards creating and really wanting to make others feel something through my art.

It began with a photoshoot idea that I had and wanted to bring to life in my front yard. I knew that for this shoot that I wanted to move away from the very fun and colorful wigs that I was previously wearing and have long black hair that was in some sort of Afrocentric style. I also knew that I wanted to be outside with flowers and wear a bold headpiece of some sort. I very much wanted to show the power, strength, and beauty in being Black.

Feinstein: Where else are you drawing inspiration?

Chris: Music is always a huge inspiration for me and at this time in particular I was obsessed with a new album by two insanely talented, beautiful Black queens, Chloe x Halle called 'Ungodly Hour'. The first song on the album, after the intro, is titled 'Forgive Me' and for some reason I felt compelled to use those two words as the caption for my photo. Considering I was this 6'4" black man holding a bouquet of flowers and wearing a wig, pretty makeup, and tank top that I DIY'd, it's almost as if I was saying "Forgive me for being strong and confident in who I am and where I come from. Forgive me for not letting society tell me who I can and cannot be."

I was so proud of the photos and I honestly felt a difference when I posted them, from when I'd usually post. I also noticed that people were more responsive to these photos than to other photos in the past, so I felt like I was doing something right and headed in the right direction. Things really started to shift when I created a fluffy pink outfit, and decided to put pink flowers in an afro wig that I had recently purchased and pose in from of a blossoming tree in my backyard. This was when I proclaimed that I was "a wildflower at heart".

Feinstein: Photography seems to be just one tool within your larger artistic practice - are looking at any other photographers’ work right now?

Chris: I honestly wouldn't say that I'm actively looking at any photography in particular but I am always very inspired by different editorial photos that I see on the internet! I love scrolling through Twitter or Instagram and seeing one of my girls like Zendaya, gracing the cover of Essence Magazine, looking just as beautiful as ever! Same goes for when I see Beyonce` killing it on the cover of Vogue, wearing these beautiful garments and big hair on lavish sets. I get very inspired when I see photos like that that represent such beauty, power, strength, and elegance! With this series, in particular, I've been very inspired by nature.

I love roaming around and seeing many different flowers blooming and just admiring the beauty within them. I've been feeling more connected with the beauty of nature than I ever have before, almost as if I see a lot of myself in nature, if that makes sense. The feeling is kind of hard to explain but sometimes I even get emotional as I was a beautiful sunset or sunrise, I don't know but it's almost as if those moments feed my soul and give me hope.

Feinstein: That totally makes sense — it feels like a needed space for peace right now. Did you have a sense from the beginning that you wanted this to be a longer-term series?

Chris: I actually had no intentions of making this a series at all, it just kind of happened, but I'm so happy that it did! The responses to those images were so positive and so powerful and honestly so uplifting, that I knew that I had to keep going.

Feinstein: You mentioned that your mom has been snapping the photos - do you consider her a collaborator/ part of the process? How involved is she beyond pressing the shutter?

Chris: My mom has always been my biggest supporter in everything that I do. She's always been the one who's in the front row, cheering me on the loudest. For the most part, I would always take my photos by myself using my iPhone, a tripod, and a self-timer. It was actually a specific photoshoot that I was working on and the photos on my phone were just not cutting it at all, and my mom suggested that I use my grandpa's old camera to take the photos and she offered to shoot them for me! This was the first blue look in the series where I embraced the fact that "boys can be princesses too".

Feinstein: How involved is she beyond pressing the shutter?

Chris: I was in love with the photos and it was super helpful having her take the photos for me so she was kind of stuck being my photographer from that point on haha! I wouldn't necessarily consider her to be a collaborator since I kind of direct her to which way I'd like the photos to be and what vibe I'm going for, etc. but I would say she's definitely a part of the process and she's always there to offer another set of eyes if I'm torn between how I want the set to look or how I want to wear my accessories, etc.

My mom isn't the most artistically creative person but I know that she likes to be involved and feel helpful so I'm glad that I can have her helping me in this way. I actually had her build the set for one of my recent shoots and she did a great job so I feel like it actually gives her more of an opportunity to tap into her artistic side. I would still consider these self-portraits if I had to lump them into a specific category but at the end of the day it doesn't really matter to me, it's just my art.

Feinstein: You mention that one of the biggest pieces of this work is a joyful rejection of toxic masculinity. A warm embrace that "boys can be princesses too."

Chris: Yes, as this series began to flourish into what it is, I definitely realized how important it was for me to send positive messages that rejected the toxic masculinity that has been consuming our society for so long. It's definitely something that I've always had to deal with, even when I was younger, just growing up and being "different" from all of the other boys. I used to play with dolls when I was younger and whenever I convinced my little sister to play "Wizard of Oz" with me, I'd always want to be Dorothy because she was my favorite character. When you're that young, like 5 or 6 years old, you don't see anything wrong with that. At that age, you're literally just living your best life without a care in the world.

It wasn't until I got a little older, that I realized that sometimes society doesn't necessarily embrace young boys wanting to play with dolls or wanting to dress up as princesses. It's honestly so annoying how normalized it is to throw something as simple as clothing into different categories such as masculine or feminine or even suggesting that a piece of clothing can only belong to a specific gender. It's ridiculous, honestly.

Feinstein: We have a 2 year old daughter and any time we take her outside in an outfit that isn’t a pink dress, people assume she’s a boy. They don’t even ask - it’s just an immediate “he.” I have no idea how she’ll ultimately identify, but it’s frustrating – even with the progress we seem to be gradually making – how early on we ingrain these ideas into children.

Chris: Even as a teenager, I hadn't fully come to terms with my sexuality or who I truly was and I felt I had to dress a certain way to appear more masculine. It's so crazy to think about it now but I used to tell myself that wigs and makeup and dresses were only for women because I feel like I was taught that that was right.

Now that I'm older and more secure enough with myself and my masculine and feminine energies (as everyone should be), I definitely want to use my voice and my platform to show everyone that "boys can be princesses too"! I know that, at the end of the day, not everyone is going to understand and grasp that concept but I still want to represent and at least try to help people see that there is no "right" way that a man or woman should dress simply because of their gender. We should all be able to express ourselves how we want.

Feinstein: Has making this work given you new insights into your experiences with toxic masculinity?

Chris: I would say that this work has definitely given me new insights into my experiences with toxic masculinity simply because I am putting myself out there in a way that I never really would have before last year when I did start wearing wigs and makeup etc. It kind of opened up the door for more people to express their toxic masculinity by commenting that I'm not a man simply because of what I'm wearing or saying that it's "sick" that I'm choosing to dress like this.

Of course, I don't let those few negative comments get to me but it does show me that there is still some work that needs to be done when it comes to teaching children and adults that you don't have to dress or act a certain way to be "manly" or "ladylike". Although there are some people who don't understand yet, I have received an overwhelming amount of love and support for my art from beautiful people all over the world!

Feinstein: Despite the negative comments, have positive comments and the popularity of this project helped your self-confidence?

Chris: The love and support that I have received has definitely helped with my self-confidence. Having people tell me that I've inspired them or even just having people refer to me as beautiful is so crazy to me. Growing up as a young black man, you don't really get told that you're beautiful, it's always "you're so handsome." Although I believe that beauty and self-confidence comes more from the inside, it feels good to have people think that what I'm creating is beautiful.

Feinstein: That’s wonderful. I can imagine the sense of power and joy would be remarkably helpful to others as well?

Chris: The response to this series has truly been amazing! I never would have expected to connect with so many beautiful individuals through this art. People have been using my art to inspire their art pieces, which is insane to think about! Even having people tell me that I've helped them to feel seen and understood, feels incredible, and makes me emotional. The overwhelming amount of love and support honestly just inspires me so much to keep going and keep creating! I'm so excited to continue to share my art with the world and continue to inspire and be inspired.

These Self-Portraits Show That Boys Can Be Princesses Too