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Meet Sydney Walters of Greyboy in Logan Square

Today we’d like to introduce you to Sydney Walters.

Sydney, please share your story with us. How did you get to where you are today?
I’ve always had jobs and hobbies revolving around children and art. Those are probably my biggest passions.

In college, I was interested in Fashion and Photography. When I started studying Fashion Design, I was the only one of my class designing kids clothes. Most students were working on a couture fashion line and I felt a little outcast, designing children’s clothes because I didn’t even have children or know that much about children’s fashion. But it excited me. I started a blog (Little Face) that was a children’s art & design blog, where I got most of my inspiration.

I ended up getting discouraged from Fashion Design, and finished college with my degree in Photography (which is currently my “day job” — working as a photographer at A Little Photo Studio — and I love it!) After undergrad I got my Masters in Art Education. Having all this knowledge and various backgrounds, (and two kids)… I had a burning desire to grow a business for myself (and them), and I was still passionate about children’s fashion.

My sons are “Lincoln Grey” and “Julius Grey” hence the name Greyboy.

Greyboy brand started in the summer of 2014, soon after having my first son Lincoln. I started to teach myself screen printing and created a “brand” for fun. Making city themed shirts and plush. It was a hobby that took off.

After lots of practice, lots of trial and error, lots of experiments, 2017 was the year I decided to go for it. And I haven’t looked back. Greyboy drives me to do what I love. I get to play with different mediums (design, screen printing, drawing, sewing, photography) I fell in love with the process of creating.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
If the road is always smooth, you aren’t going the right way. I am learning so much from every error, mistake, and flaw.

Being a single mom has its daily challenges, but I’m becoming a professional juggler of life. Balance and patience are probably my biggest personal struggles.

I always have to do every part of the business myself. I give myself SO MANY projects. I’m not sure if its because I want to learn everything, or I hate asking for help, or I’m a control freak. At the end of the day I’m usually exhausted, and brain dead, but also happy. There is a lot of pride in growing something yourself. But I do need to slow down sometimes.

Running your own business can be isolating at times, spending a ton of time in your own head, you question your ideas and doubt yourself. Luckily I have a kick-ass group of business ladies, close friends and family who have been pushing me to keep going and picking me up when I fall, and I’m forever grateful for them.

We’d love to hear more about your business.
Greyboy came from a lack thereof. I was always in search of boy clothes that didn’t scream I’M A BOY I LOVE SPORTS. But I also noticed that design doesn’t need a gender. I focus on designs that all kids can enjoy and relate to. Designs are hand drawn, playing with ideas of nostalgia, street style, and imagination. Most of my inspiration comes from my kids and our beautiful city of Chicago.

I’m most proud of the handmade aspect. As well as Greyboy DIY workshops; which take place at local businesses and venues, where kids come and create together.

I currently run “Greyboy headquarters” out of my two bedroom apartment in Logan Square that I share with my 2 sons and our bulldog Prince. All printing, sewing, labeling, designing, branding, marketing, organizing, photographing, etc is done in a makeshift in-home studio. Which allows me to get a lot of help from my own Grey boys. I love that my kids are involved in the process.

What were you like growing up?
I wanted to be a creative entrepreneur at a young age. I was always coming up with these elaborate business concepts in my journal. When I got my first sewing machine, I didn’t stop sewing, including my prom dress. I took photography all 4 years of high school and loved being in the darkroom. I’ve always been extremely independent and stubborn. When I have an idea in my mind, I usually make it happen.


  • city train hoodie $36
  • pigeon football tee & onesie $28
  • chain fence acid wash romper $42
  • boombox sweatshirt $32
  • pigeon reversible infinity scarf $18
  • greyboy city plush DIY kit $26

Contact Info:

Image Credit:
A Little Photo Studio

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