Canvas Rebel: Meet Jessy

Canvas Rebel Interviews Jessy, founder of Titty City Design

Entrepreneur Interview

Originally published on Canvas Rebel

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Jessy, thanks for taking the time to share your stories with us today So, naming is such a challenge. How did you come up with the name of your brand?

This is a fun one! My brand is called Titty City Design. It’s hard to not smile or laugh when you say it. Which is a bit by design. I am on a mission to break down barriers and destigmatize breasts, and what better way to do that than by making people smile? As soon as you say Titty City out loud, you may giggle. In fact, you are likely going to be curious and ask, “What is Titty City Design?”

I love seeing this in real life when I am out at local events and pop-up markets. All day long I hear laughter and people saying things like, “Look! It’s Titty City!” People of all genders, ages, and backgrounds show a genuine curiosity. When people come into the Titty Tent (that’s what I call my pop-up store), they want to know what Titty City Design is about. So I tell them!

At Titty City Design, I create body-positive products that feature a variety of hand-drawn breasts to promote self-love and body confidence, celebrate new moms and their breastfeeding milestones, and advocate for breast health. We also give back to the breast cancer community.

And then it clicks for them, and this is where the magic of my brand begins to happen. Immediately a wall comes down and the curious customer begins to share a personal story about their experience with their own breasts, or someone else’s story. And this is what my brand is truly about – getting people to openly share about their breasts to help remove the shame and stigma around them. That way, we can better support one another when it comes to topics like body image, breastfeeding, and breast health.

But, I still haven’t answered how I came up with the name, Titty City Design. Well, to put it simply, the name came from my breastfeeding journey. Breastfeeding my son is what inspired my entire brand.

When my son was hungry, I would say, “It’s time for Titty City.” And it stuck. It was fun, and it made me smile, even though my breastfeeding journey was incredibly exhausting, draining, and so much work. Breastfeeding for one year is equivalent to 1,800 hours – It is literally the same amount of time as a full-time job with 3 weeks of vacation. And it is hard! To call nursing, “Titty City” made it feel a little less hard at times.

When I first doodled my signature “Titty City” design, featuring a variety of breasts in all shapes and sizes, it was only natural to me to make it my company’s name. It’s fun, brings a smile, and helps bring up conversations about breasts, a topic that is usually not talked about in a non-sexual context.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Hi! I’m Jessy and I’m the Tits behind Titty City Design. I’ll tell you more about that in a bit, but first, let me share a little about myself. I was born and raised in the suburbs of Chicago and graduated with a BFA in graphic design from the University of Illinois. I found myself longing to be near the ocean, so I moved to California, where I built my career as a creative director and met my soulmate. We now live with our toddler and labradoodle in the South Bay, where we call home. Just over a year ago, I left my corporate job to pursue entrepreneurship and put all my effort into building a brand of my own, Titty City Design.

I started this body-positivity brand to celebrate new moms and breastfeeding because breastfeeding can be SO hard, and it deserves to be supported and recognized. My brand also advocates for breast health and gives back to the breast cancer community. We truly celebrate all the Boobies!

At Titty City Design, I create products that celebrate our bodies and help to strike up conversations about “The Boobment” – Yes, you read correctly! “The BOOB MENT” is a social movement that I started to normalize talking about our breasts! Especially about our experiences with breastfeeding and about breast health.

My body-positive products (like boob mugs, boob socks, boob hats, hand-painted boob flowerpots, and so much more!) are intended to make people smile, feel seen, and celebrated. Breasts are a part of our lives, and they should not be ignored or shamed. In fact, they should be supported, like a good bra!

I’m an advocate to my core and work tirelessly to build this community — in real life, on social media, through my products, and with my “Let’s Talk Titties” blog — that promotes body positivity, and celebrates new moms and breastfeeding, and promotes breast health.

I find it so hard to believe that in 2023, talking about breasts and breastfeeding is still taboo. People truly whisper the words: ‘breasts,’ ‘boobs,’ and’ titties’, and act uncomfortable talking about them. This is because our culture and society have notoriously shamed and sexualized our breasts starting from a very young age.

I believe that by talking openly and candidly about our breasts and experiences with them, we can take back the power from those who oversexualize our bodies. Instead, when we talk freely about our breasts, we can empower each other and help promote body acceptance, body confidence, and self-love. We can help educate and provide resources on breastfeeding and postpartum and make the transition into motherhood feel less lonely. And by talking openly about our breasts, we can encourage each other to take better care of our breast health —because 1 in 8 women will be diagnosed with breast cancer in their lifetime.

The inspiration, or rather the, ‘Tits-piration,’ for my brand came from my breastfeeding journey. I became a mom at the beginning of the pandemic in 2020 – the year that changed everything for so many. The postpartum journey tends to be incredibly isolating, and for me, it felt remarkably lonely to become a first-time mom at the beginning of a global pandemic.

Transitioning to motherhood while going through quarantine was unlike anything I could ever imagine. There were no local mommy and me classes, no meeting up with friends or family, and no physical support outside of my home. The ‘new mom struggles’ were real.

I didn’t realize how challenging postpartum, and breastfeeding would actually be prior to becoming a mom. No one ever talked about it around me – which is not uncommon, by the way. On barely any sleep, I worked from home, with my baby always on the boob — for feeding or for comfort. After experiencing almost every breastfeeding struggle, I truly understood how incredible and strong mamas are.

All at once, we learn to breastfeed, care for a new human, and recover from giving birth on the bare minimum of sleep. It’s mind-blowing! Not to mention, becoming a mother is a whole other identity that takes time to adjust to and can make you forget the person you were before.

To get back in touch with my creative self, I channeled my awe for motherhood through art. I began to paint my ‘Titty City’ design on ceramics while my baby was asleep as a form of self-care. While painting, I thought of the other new moms out there experiencing this, too. I wanted to reach out, hug them, and let them know they weren’t alone.

In November 2020, I was inspired to create Titty City Design — a brand that speaks to new moms — and build a community that empowers and encourages each other with love and positivity. I strive to shower new moms with praise and support while working to break down barriers and normalize talking about breasts and our experiences with them.

I believe, that the more comfortably we share about breastfeeding, the more normal it will become, and the more support and encouragement we can offer to our fellow “Milk Makers” on their breastfeeding journeys. Whether you breastfeed your little one for days, weeks, months, or years… I want every birthing parent to know this: you are amazing and deserve to celebrate your breastfeeding milestones!

My best-selling product is a boob mug covered in my original ‘Titty City’ design that brings a smile to anyone’s morning routine – but especially to a breastfeeding mom that is exhausted and will likely need to reheat their coffee several times before finishing their drink. Our Boobie mug is truly one of the best gifts for new moms that they least expect. Nursing on demand is no joke, but our Hot Tits mug (yep, we call it a “Hot Tits” mug) will be sure to make a new mom smile.

If you are looking for gifts for new moms that aren’t for the baby, we have the best baby shower gift ideas. Our unique gift sets for new moms are super popular and make the perfect baby shower gift for the mom. The truth is, the baby doesn’t need too much, but they do need a healthy mom that feels supported and encouraged which is why my new mom gift baskets are ‘Simply the Breast!”

I have a variety of new mom gift sets, with adorable names like, “Keep on Boobin’,” “Hang in There,” and “Back to Work Mother Pumper.” Our new mom gift baskets feature items like an oversized, ‘You’re the Tits’ water bottle to make sure the new mom is staying hydrated, and TitTies Hair Tie Bracelets that can be used to make the perfect mom-bun or serve as a breastfeeding reminder band to help determine which side to feed on next.

Our products aren’t just for new moms, although they do make the best postpartum gifts and postpartum care packages. As a proud feminist brand, we support women’s rights, promote body confidence, and empower women+. We also have so many body-positive gifts that are great to give to youngsters and beyond. My designs feature a variety of breasts in all shapes in sizes because no pair are alike, and it is important to see this type of representation and promote self-love.

I also have an entire line of the best gifts for breast cancer patients that feature mastectomy scars. I call it my “Brave Boobies” collection and it is filled with the most thoughtful gifts for mastectomy patients. Breast cancer sucks! That’s where we come in. We make care packages designed especially for your Breastie to let them know you are in this together. And if you are looking for the best gift for a breast cancer survivor – because they just kicked cancer’s butt – you need to check out breast cancer survivor gift sets.

The bottom line is that no one should have to go through breast-related experiences alone. It’s important to feel seen and supported and encouraged. And that is what Titty City Design stands for.

Choose the perfect gift from our shop to celebrate your own body, or to show love, encouragement, and support for your fellow breast friends and loved ones.

Shop our self-love products, baby shower gifts that are for the mom, breast cancer patient gifts, and more at Be part of “The Boobment” with us and join us on Instagram (@tittycitydesign) and TikTok (@tittycitydesign). A portion of our proceeds are donated to help support postpartum people and breast cancer patients. Your support truly means the world to me, my family, and all those out there that are feeling lonely on their breast journeys. We can make a difference together. Let’s break the stigma around breasts and celebrate our bodies!

How did you build your audience on social media?

My company started on social media. Truthfully, I did not intend for it to become what it is today. I didn’t have a plan at first. Starting Titty City Design was a happy accident. Let me explain. So, I had my son in February of 2020, weeks before the world completely shut down. I was on parental leave from my job as a creative director – at a Fortune 500 company, and my motherhood journey was off to a really tough and lonely start. When I say lonely, I felt completely alone. Not only was I quarantining at home with my newborn, but I was not in touch with any adults outside of my home. I was feeling really lost.

To get back in touch with my creative self, I began painting. With inspiration from my breastfeeding journey, I painted breasts on ceramic pots. It felt so relaxing to me and was an escape from my role of, Chief Feeding Officer. Before I knew it, I had several boob-painted pots – dozens really.

I posted photos of them on my private Instagram account, and my friends loved them. I was getting asked if I could make my profile public so that my friends could share my artwork.

As it turns out, I made a handle on Instagram for @tittycitydesign because that is what I was calling my pattern, inspired by my breastfeeding journey. I started to post my pots on my Instagram account and it wasn’t long before people were sharing my posts and following along. Then, people started sliding into my DMs (direct messages) asking to purchase my hand-painted boob pots. I thought, “Wow, this is great!” because I truly didn’t know what to do with the dozens of pots I had painted.

From there, I sold in my DMs and eventually transitioned to an Etsy shop and progressed to launching my very own website that I built using Shopify in April of 2021.

As far as building my audience on social media goes, I just kept showing up on my feed. Every day, I posted my work. I would get new ideas from my audience, and I would experiment with what was requested. I noticed that as I was interacting with my followers, I was actually building a community and real friendships, too. This helped with my lonely motherhood journey, and I realized that I was on to something. I was not alone anymore. In fact, I was not alone at all. There are thousands of people that were seeking community and connection through my work.

The demand for my hand-painted items increased, and I simply could not keep up. I had the full-time job that I had returned to, a baby, and Titty City Design to juggle. I didn’t know how I was going to keep up.

Building a social media presence is unpredictable. What worked for me is creating content for a very specific niche, showing up consistently, and being my authentic self. I believe it should feel fun and build real connections with your audience.

Okay – so how did you figure out the manufacturing part? Did you have prior experience?

Since the demand was increasing, I had to figure out a way to scale, because I simply could not hand-paint all my items. That is when I used my resources from my years in the graphic design and marketing industry. I reached out to an old colleague of mine that sources products to discuss my first order with my design printed on it.

Then, I surveyed my Instagram community and asked what product they wanted next. I was overwhelmed by the request for a mug! So there it was, I started creating the layout of my Hot Tits mug. I showed it to my audience and opened a pre-order. I had around 80 boob mugs sold, right off the bat, before I even placed an order at the printing shop. It was wild to me, and I realized that I was doing it – I was starting a business.

Once I had the mugs going, I was already brainstorming – I mean “Boob-storming” – my next product. I was very resourceful and was able to track down manufacturers to produce my product ideas. I sourced Boob socks, Titty hair ties, Boobie beanies, Titty hats, Titty tumblers, Boob phone cases, Titty tote bags, Boob-danas, Boobie beach blankets towels, and all sorts of apparel.

I design every single product and work hard to have them locally produced. Quality and eco-friendly materials are also a priority for my products. Whenever I am unsure of what product to create next, I just listen to my audience, and let them guide me on what they are looking for.

Along with my printed products, I still have my hand-painted Boobie flower pots available in my online shop. I’ve got a lot to learn, and I am trying to navigate wholesaling my products. For now, my body-positive products are only available in my online shop, or at one of my live events. This year, I have been trying to do at least one local event a month where I bring my Titty Tent and sell my boob-themed products in person throughout Los Angeles and the surrounding areas.

I love getting to interact in real life with my customers and build relationships with people that are spreading the message of the work I do. It gives me confidence and assurance that there is a need for Titty City Design, and the empowering message it delivers.

If you are local to the LA area, come see me and the Titty Team (my amazing team of helpers) at one of my Titty Tents. I have all my events posted on my website. Look for “Pop-ups” in the main navigation at I hope to see you at one in the future!


Contact Info:

Image Credits
Jessy, Titty City Design