Windy City
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Windy City
Windy City Apparel offers custom screen printing, embroidery and promotional products. Our designers bring your vision and ideas to life. Our team has over 50 years of combined experience in the industry using state-of-the-art equipment. We understand the importance of accuracy, clean design and high-quality products.

We work hard to earn your business and want to keep you happy! Call (941) 351-4205 for a FREE estimate! From school uniforms and athletic and band gear to business and restaurant uniforms, we've got you covered! Contact us today. With over 50 years of combined experience, you can depend on Windy City Apparel to work with you on your idea and make it a reality!
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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.
From school uniforms, athletic and band gear to restaurant and workwear, and everything in between, we've got you covered. The process begins with the art. Windy City Apparel will work with you on your idea and present it for approval. Once approval of the art on a virtual mock up is given, the design is then broken down into separate colors.
Windy City Apparel offers custom embroidery services. Embroidery is our specialty and is a great choice for jackets, polos, hats, bags, fleece and t-shirts! Our Embroidery department can handle orders ranging from two dozen to several thousand pieces. We can take care of all your embroidery needs from logo creation to digitizing.
Reviews (9)
Ron Cobb
Ron Cobb
Jul 19, 2019
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Windy City Apparel has been our company's go to apparel firm for over a decade. They have provided us with quality services beyond reproach, cost competitiveness & and do what it takes over and over to meet our schedule! The Carollo's have a well run successful family business.
Lucia Mendoza
Lucia Mendoza
Jul 16, 2019
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I started using Windy City Apparel on September 2018 and their customer service exceeded our expectations. We are a Bible Institute and had commented with Stacey about our picture day in one of our meetings. I wasnt expecting it but she worked towards having everything on time even though we had some late student orders. I am very please with the quality of the shirts and amazed at their customer service, it's outstanding. Will highly recommend.
Google User
Google User
Jul 10, 2019
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I found Windy City Apparel by chance and what a great find it was! I spoke with Stacey who was able to get me an estimate the same day and she beat the price of our previous vendor. I ordered the shirts for our company from her and the process was quick and easy. We received a quality product at a great price. Our landscape company is very happy with our new uniform shirt vendor.
Jeff Sturgis
Jeff Sturgis
Dec 03, 2018
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The owners and staff are some of the best people I have ever met. The design stages were very impressive. The delivery was very fast and the quality was very good and all for a reasonable price. I will be placing more orders with them.
Jill Rothery
Jill Rothery
Nov 28, 2018
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I have been doing business with Windy City Apparel for several years. I am the manager of a restaurant that is always ordering shirts and aprons for our wait staff and our kitchen crew. I appreciate Stacey & Dolores always dealing with my sometimes confusing/difficult orders so professionally. All of the products we have received from them have been top-notch quality. The embroidering and screen print are always flawless. I would also like to add that my daughters school uses them for their uniform needs. Many choices to choose from and again, outstanding quality. My orders have always been received
Dan Sidler
Dan Sidler
Jun 22, 2018
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Our organization worked with Winy City Apparel on a recent project and we were more than impressed. Stacey and her team went above and beyond in delivering a first-class product with excellent customer service. Five stars!
Propel Builders
Propel Builders
Nov 26, 2017
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Great customer service. Stacey and her team were great to work with and they were very helpful in getting our company shirts embroidered, plus they were able to help with some special order items. Highly recommended.
Angela Maasdorp
Angela Maasdorp
Jun 30, 2017
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I have personally used Windy City Apparel for the past 7 years. We have travel basketball teams and have used this company time and time again. Of course we always end up needing our product in a hurry, Dolores and staff always come to the rescue! From the helping us pick out exceptional product, the ordering process, keeping us in the loop about product, payment and timely delivery of finished work, we cannot complain! Windy City is the absolute top notch apparel company in the area to fit your needs. Can't thank them enough!!
Sarasota Ballet
Sarasota Ballet
Jul 28, 2016
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Windy City Apparel is fantastic to work with. We have placed several large and small customized orders with Windy City Apparel and each order has been completed timely and with great care. Windy City Apparel provides excellent customer service and high quality products at a reasonable cost. Everyone that we have worked with has been extremely helpful, friendly and very professional.