Meet Jess Oakes, Founder of Positively Oakes

Meet Jess Oakes, Founder of Positively Oakes

We’re honored to introduce you to Jess Oakes, founder of Positively Oakes, an accessory company for all the baby fashionistas out there and their moms as well as an amazing lifestyle blog.


What is the Positively Oakes shop, and how did you get the idea for it?

Positively Oakes has two parts to it: we’re a comfortable accessory shop and children/motherhood lifestyle blog. The inspiration behind the shop part of my site came entirely from my grandma; she was an amazing seamstress and I learned everything I know about sewing from her. This was a way for me to honor her memory and do something I love.

The entirety of Positively Oakes was created for one sole purpose: realness. Here, we chat and celebrate motherhood, mom-bossness, dance to the song “Happy” often, spread positive awareness, and get our shop on. We chat about the good, the bad, and the ugly, recommend the latest and greatest in baby products, and like we said keep it real and honest with you. With motherhood comes being a mom boss: A mom boss is a number of things; a warrior who tames little babes and helps them grow and develop while tackling all the work around her and attempting to stay sane.

Recently at Positively Oakes we created the campaign #dontwastehappy, where we promote being yourself, being happy and not letting anything bring you down—this is where our positive awareness comes into play. We want every person to feel important, strong, and know they can do anything they put their mind to.


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How has the business grown and changed since you first started out?

It has grown and changed quite a bit! We started on Etsy where we were just a small children’s shop and in about six months (after really pushing social media) had done of 2,500 sales—so we started out on our next venture!

I had always wanted to create a center for motherhood to be supported, chatted about, and a place where we could support each other. With the change of growth in our sales came the next step in our journey. We created our current site, where we have our blog and shop all in one. We are constantly changing and developing new ideas and adventures to keep up with the changes in life and developments in Children’s products and Motherhood.


What’s one challenge you had with your business, and how did you overcome it?

The biggest challenge I had was getting over the comparison game. I chatted about this recently on our blog too. With running your own business/blog comes so many comparisons; you’re constantly looking at other people’s businesses and social media and comparing yourself to them. Obviously this gets someone nowhere, so I had to learn that it’s okay not to have the highest numbers, or the best of the best. I always strive for greatness, but am learning to be happy with me, and what I do and have now.


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What’s been the most surreal moment of running your business thus far?

I would probably say there’s been a couple. When my hard work has paid off and we get a big feature or recognition is constantly a surreal moment and extremely rewarding. There’s so much that goes into Positively Oakes behind the scenes that people don’t see, so when something even little is recognized, it’s a huge milestone and seriously brings me such excitement and happiness! Another big one would be when Jessie James Decker’s little girl wore one of our headbands from our shop on Instagram—that was DEFINITELY surreal!


What advice do you have for women hoping to start businesses of their own?

PATIENCE. That’s my biggest piece of advice. Sounds redundant I know…but I am totally serious. Everyone used to tell me this and I hated hearing it, but it’s the truth. Your dream is not going to happen over night. It takes serious dedication and effort. I work 14 to 15 hours a day sometimes (actually, most days) and am constantly racking my brain for the next thing. But my advice: DON’T give up; keep going, even when things seem hard and like you’re going to hit rock bottom. It will turn around and you will achieve your goals.

You can follow Positively Oakes on Twitter, Facebook, Instagram, and Pinterest.