Can I legally sell a brand-name item if I decorate the item with my designs?

I am making plans to start a small business with a partner in my hometown. Some of our plans are to decorate clothing items, including Hanes shirts and socks, and Keds shoes. If we decorate these items with our designs can we legally sell these items without penalty? Also, can we trademark our company if we are using products that are already trademarked?

You’re treading in murky waters here. Generally, you are not legally permitted to trade off the brand name of another.

However, you may be able to get trademark protection on the designs you create. To make sure you navigate this area in safety, consult with an intellectual property attorney who is familiar with working with apparel companies.