We recently connected with Lindsey Radoff and have shared our conversation below.

Lindsey, looking forward to hearing all of your stories today. What’s the backstory behind how you came up with the idea for your business?

I’m Lindsey Radoff, and I’m a mom to two little ones, Sienna (7) and Austin (4), and the proud owner of Thoughtfully Hooded, a collection of boys clothing that all have snappable, swappable and easily detachable hoods. The idea for Thoughtfully Hooded came to me when Austin was 3 months old. I would get him dressed in his cute little hoodies, and yet every time I would put him in his car seat, I felt like there was so much fabric behind his head that it would push his head forward and I didn’t like it. When it would be time to nap in his crib, I didn’t like the idea of all that fabric surrounding his head from the hood. And then one day it hit me — there should be a collection of everyday clothing where the hood snaps on and off. I started with boys clothing because like so many of us, I recognized there was a huge void in the marketplace for cute boys clothing. Plus, I used my son as my inspiration.

I have no design background and am a one-time lawyer turned real estate agent turned stay-at-home mom, so naturally my journey into design started with a Google search; “How do I start a children’s clothing brand?” Thoughtfully Hooded launched in October 2021, just two months shy of Austin’s third birthday. And it was received so well by my local San Diego community, with major stores like Nordstrom (Fashion Valley and UTC) and Pottery Barn Kids (UTC) inviting me to hold pop-in shops in their stores. And then just 7 months into our brand’s launch, we officially became available online at Nordstrom. It was a huge accomplishment and something I’m so proud of. It literally still feels like a dream!

We are getting ready to launch our second collection, which will include six new pieces including two adorable bomber jacket, two long-sleeve henley shirts and two more button-down shirts.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

A little about me … prior to having my kids, I was a lawyer turned real estate agent turned stay-at-home mom to Sienna and Austin. I’ve always had an entrepreneur spirit; I just didn’t know what to do with it. It wasn’t until Austin was 3 months old that I finally found my calling when I came up with the idea for a boys clothing line with snappable and swappable hoods. I have no design background but was determined to launch this brand!

What really sets our brand apart from other brands is our removable hood in everyday pieces. Before I launched Thoughtfully Hooded, I hadn’t seen a collection with a removable hood in anything other than a jacket. Our collection consists of button-down shirts, henleys, zip-up jackets and bomber jackets. Each of our shirts comes with two hoods, so that you can mix n’ match and change the look of the shirt simply by swapping the hood. All our hoods are also interchangeable throughout the collection, making it fun to change out the hoods. And all our snaps are hidden so that the shirt can be worn without its hood (because I know there are plenty of days when your child might not want to wear a hood!).

All of our pieces are designed with a lot of thought and care, which is something I’m so proud of. I love that we started with boys because there is such a void in the market for fashionable boys clothing.

I am also extremely proud of our giveback initiative. As a cancer survivor (I was diagnosed with thyroid cancer while pregnant with Austin), I also wanted to be a voice for mothers diagnosed with cancer while pregnant, a group often overlooked in stories about both parenting and cancer. I donate a small amount of proceeds to Hope for Two, which offers free support for women diagnosed with cancer while pregnant.

Can you share a story from your journey that illustrates your resilience?

I think my whole journey, from concept to prototype and through production, all illustrates my resilience and my never give up attitude. I had the idea for my clothing line when my son was just 3 months old, and yet it didn’t launch until almost 3 years later. So, the brand didn’t just happen overnight. My biggest obstacle at first was me! Because I have no design background and had been a stay-at-home mom for so long, I didn’t know where to begin in developing a children’s clothing brand. I worked for months trying to learn the ins and outs of the industry as I went, making plenty of mistakes along the way. As I was finally beginning to hit my stride, the pandemic started in 2020, halting production, just like it did for so many other businesses. There has definitely been a lot of ups and downs but through it all I never lost site of the end goal and am so proud that I was able to reach it — and we are just getting started!

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

The first step to bringing my concept to life was seeking out a great pattern maker. I had no idea how to make a pattern, manufacturer a product, or even source fabrics! I just knew what I wanted my brand to look like and sought out a team who could help me see that vision through. I spent about 10 months working with my first pattern maker and development team, and after making a number of unsuccessful attempts at my shirts, realized it wasn’t the right fit for me. I parted ways, disappointed that I had spent so much time and money and didn’t have a product to show for it. But instead of being discouraged, I used it as a lesson and now had a clearer vision of what my brand looked like. I went back to the drawing board and luckily found an amazing pattern maker in Los Angeles who understood my vision. Once we completed the patterns, I was fortunate that she introduced me to an amazing team who has been instrumental in helping me manufacturer my collection.

I’ve learned so many lessons about the manufacturing process, one of the best is to listen and take guidance from those who know more than I do. You have to put a lot of trust in the team you’re working with, so never be afraid to ask questions. Always be able to pivot as there are so many moving parts. There can be a lot of challenges and frustrations but picturing the end goal and never losing site of it, helps make the process that much more rewarding.

Contact Info:

• Website: www.thoughtfullyhooded.com
• Instagram: thoughtfullyhooded
• Facebook: Thoughtfully Hooded

Image Credits
Alana Ziman Amber Greenburg Arielle Levy