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About Windy City Apparel

Get A Quote  | Quick Turnaround Time | Competitive Pricing

(941) 351-4205

Who We Are


Windy City Apparel was started in Chicago in 1979 by (then just a kid) Tom Carollo. He began screen printing shirts out of his parents' basement and grew the business so much that he quickly had to get a storefront to accommodate. In 1989, he moved to the Sarasota area and started from scratch once again. The business grew legs, spread to a nationwide reach, and the rest, as they say, is history!   


Windy City has always provided our customers with sincere, honest, and respectful customer service. We treat you how we would like to be treated. Our team also adheres to a strict quality control policy, ensuring the products we hand to you look crisp, clean and are exactly what you want. We realize there are many options for embellished sportswear and promotional items, and we want and expect to earn your business. For a FREE estimate, call (941) 351-4205 or stop by!

Year Established



  • Custom Screen Printing

  • Embroidery


  • Classroom Colors


Payment Types

  • American Express

  • Cash

  • Check

  • Discover

  • MasterCard

  • PayPal

  • Visa

  • Zelle

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