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Writer's pictureLive Oak Management

Fashioning My Future: The Journey of Owning a Small Business

Updated: Nov 12

Written By Skylar Zimmerly

Creative Member





As a current sophomore in college, it’s surreal to reflect on my journey as the owner of a small custom clothing business, a venture I started back in my first year of high school, which I never imagined would grow this large. What began as a lifelong dream at the time, which then turned into a hobby, is amazing to see what is possible when given the resources and support. 


Growing up, I always had a creative side, and I was mainly focused on the fashion industry. With the beginning of COVID occurring during my freshman year of high school, this was the perfect time for me to take up a new hobby. My parents had bought me a Cricut machine for my middle school graduation. I watched endless YouTube videos to learn how to use it, especially creating vinyl decals to iron onto clothing. 


After learning the ins and outs of creating basic clothing pieces like sweatshirts and t-shirts, I created an Instagram and Facebook page to sell these simple items for my newly founded business, "Designs by Sky." Immediately after posting 

my first three items ever made, I received numerous DMs from customers my age

interested in purchasing. I also marketed my new business items on a local moms Facebook page, which helped my company take off. I started to take custom orders, which included custom masks for COVID-19, mask pouches, and clothing gifts, and my dream was soon becoming a reality. 


Fast forward to last year, my first year of college, I’ve refined my skills by creating orders for large sports teams and Greek organizations. I also perfected my social media use, which helped me create a name for myself. Bringing my business to college has allowed me to pursue numerous opportunities. Through the Oak Originals organization, I have weekly pop-up shops where students can purchase my clothes, and I continue to customize orders for delivery on campus.


Reflecting on my journey so far, I see the massive growth I have had since starting as an extremely small business with a big dream. I utilized my prior knowledge of social media and my artistic ability to draw digitally to showcase my products and connect myself with potential customers. The support I received throughout my time running this company has been overwhelming. With my future in mind, as I graduate college in two years, I’m excited to continue growing my brand. With a professional website in the works and new designs formulating in my mind daily, I plan to grow and own Designs by Sky for as long as possible. Running a small custom clothing business has shaped me into the person I am today and continues to fuel my passion for hard work, creativity, and growing the fashion industry.

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