Meet a Mom: Meet Nicole Reilly! | Chicago Moms Network

It’s Meet a Mom Monday! This week’s Meet a Mom feature is Nicole Reilly, Logan Square mom of two adorable kiddos and founder of Dear Hayden. Dear Hayden is the sweetest line of functional and elevated baby and children’s wear – made using only the softest organic materials. Keep reading our interview below, where Nicole shares all about her journey from Chicago elementary school teacher to founding Dear Hayden, and more fun tidbits about being a Chicago mom. Thank you Nicole for sharing with us today!

If you are a local mom that would like to be featured in our “Meet a Mom” series, please send an email to [email protected]


Hi Nicole! Thanks for speaking with us today. Can you tell us a little about yourself?

Thanks for having me! My name is Nicole, I am 37 years old, I am a mom of two, a former Chicago Public School teacher, and a new baby and children’s clothing brand founder.

Where are you from originally, and what brought you to Chicago?

I was born in Chicago, moved to the suburbs (Deerfield) when I was 3 1/2, went to college in Washington, DC, lived in LA for a year, then came back to Chicago to go to grad school at Northwestern for teaching.

How many kids do you have, and what are their ages? 

I have two kids, 2 years old and about to be 4.

What is your favorite part about being a mom? 

Too many favorite parts but to name a few…when they are sick and just want to snuggle, when they tell you they love you, when they wake up and call for you, when they want you to say goodnight one more time, when they cry when you leave, and when you hear them repeating something that you taught them.

Which neighborhood do you call home? 

Logan Square!

Do you have any favorite local businesses that you like to frequent? 

The Red Balloon, Longman and Eagle, Alice and Wonder, Andros Taverna, Penelope’s, Easy Does It

What are your favorite things to do in the city with your kids? 

During the warm months we go to the Logan Square farmer’s market every week, we go to lots of parks around the city, drag them to my favorite restaurants, we love the Peggy Notebaert museum, Shedd Aquarium, and the Lincoln Park Zoo.

Can you tell us a little about your career journey, and how it led you to found Dear Hayden? 

For eight years, I was an elementary school teacher in Chicago. I taught everything from 1st grade to 5th grade on the Southwest side of the city, in Noble Square, and most recently in Lincoln Park. After I had my daughter, I decided to stay at home and spend some time with her while she was little. Then the pandemic hit and I was so grateful that I was home and not navigating teaching during such a crazy time. I have always loved clothing and after I had babies I fell in love with baby and children’s clothing. I found the zip and magnetic footy pajamas for babies to be incredibly practical for night but I felt like there wasn’t a great functional option for day time. All my favorite pieces were covered in buttons and snaps and were totally impractical for constant changing. After I had my son, I started having some thoughts for a brand that made elevated baby and children’s wear that was also extremely functional. I started doing some research, talking to people in the industry, and took one step at a time to move the idea forward and here we are about two years later. We just launched at the end of November and we are available via our website as well as some boutiques across the country. You can find us locally at Red Balloon in Bucktown as well as Penelope’s in Wicker Park. All of our pieces are made sustainably in Portugal using organic cotton and other eco-friendly fabrics. Many of our pieces feature hidden, sewn-in magnets for the easiest changes and to facilitate independence in toddlers.

What do you love most about running your own business?

It’s been a huge learning experience. I am constantly learning about different facets of the business: inventory, manufacturing, fashion design, marketing, the list goes on and on. I also love that since I work for myself I have the flexibility to go to a class with my toddler or schedule a playdate when I want.

Have there been any big surprises along the way? 

Since this whole experience and industry is new to me, it feels like constant surprises. From learning about trademark applications to consumer product safety requirements to customs fees, I don’t think anything can surprise me anymore.

What is something everyone would be surprised to know about you? 

I don’t have any fashion or retail experience. I’m just a mom with a dream and an idea trying to make it work!

What is on the horizon for Dear Hayden? 

We have two drops coming in the upcoming weeks: a small summer knitwear drop as well as our core collection of t-shirts, leggings, pajamas, bodysuits, and rompers. We have so many adorable pieces made from the softest fabrics. I’m so excited for everyone to see these new pieces.  To coincide with the drops, we have some pop up events/trunk shows in the works. We also are partnering with Cradles to Crayons to help advance their mission to provide essentials to kids in Chicago living in homeless and low income situations. In the upcoming months we will be piloting a program where Dear Hayden customers can choose to donate gently used baby and children’s clothing and we will pay for shipping the donation directly to Cradles to Crayons.  Make sure to sign up for email on our website  and follow us on social media @shopdearhayden to stay up to date.

As an entrepreneur, I’m sure that you have a ton on your plate at all times! Any favorite mom-hacks or organization tips that you swear by? 

We outsourced the organization of our kitchen as well as our playroom which was a game-changer. We worked with Betsy from Neat Method in Chicago and her team was amazing. They come in and work with what you have and try to use your existing materials to organize before purchasing anything additional. It’s an investment but they put a system in place that ensures you can maintain the organization over time.

Rapid Fire Round! 

Best Chicago neighborhood: Oooh this is super tough. They are all amazing for different reasons. I love the West Loop or Logan for food and drink and Bucktown for a cute, family-friendly neighborhood.

Favorite place to travel (without kids): Japan

Favorite place to travel (with kids): Mexico

Undergrad college/major: Psychology and pre-med

Coffee or Tea: Coffee

Favorite way to start the day: I have to wash my face first thing in the morning and it helps me to feel more awake. I like to listen to the daily or another podcast while I get ready. I also really look forward to my morning cup of coffee. In an ideal world, I would wake up and workout before the kids get up but right now my son gets up too early for that to happen.

Last book you read: It Ends With Us by Colleen Hoover

Favorite movie: Bridget Jone’s Diary or You’ve Got Mail

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