She Dressed Taylor Swift, Then Built a Sports Fashion Empire: Kristin Juszczyk’s Off Season

On today’s episode, I’m joined by Kristin Juszczyk, founder of Off Season, to talk about how she went from teaching herself how to sew on YouTube to building one of the most exciting brands in sports fashion. Kristin shares the story behind her viral NFL game day designs, how Taylor Swift wearing one of her custom jackets changed everything, and the journey of turning a creative passion into a licensed apparel brand. We also discuss entrepreneurship, taking risks before you feel ready, navigating licensing deals with major sports leagues, building a brand from the ground up, balancing creativity with business, and why persistence is often the biggest competitive advantage. Whether you’re an entrepreneur, fashion lover, or simply looking for inspiration to chase a big idea, this episode is packed with actionable insights and founder wisdom. Enjoy!

To connect with Siff on Instagram, click HERE.

To connect with Siff on Tiktok, click HERE.

To learn more about Arrae, click HERE.

To check out Siff’s LTK, click HERE.

To check out Siff’s Amazon StoreFront, click HERE.

To connect with Kristin on Instagram, click HERE.

To check out Off Season on Instagram, click HERE.

To shop Off Season, click HERE.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Sleep cooler this summer with Boll & Branch during their Annual Summer Event. For a limited time, get 20% off sitewide at BollandBranch.com/dreambigger with code DREAMBIGGER. Exclusions apply.

Get $25 off your first purchase plus an extra $100 to shop when you sell for the first time. Go to TheRealReal.com/dreambigger

Go to shopify.com/dreambigger to get started now.

Text DREAM to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply.

Try Gusto today at gusto.com/DREAMBIGGER, and get three months free when you run your first payroll. That’s three months of free payroll at gusto.com/DREAMBIGGER

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.