Dress Code

At Cheshire Academy, we believe in preparing our students for a myriad of opportunities. As such, we pride ourselves on having our community members dress for success. We teach our students that a dress code, while formally expressed or not, exists in the professional world. Whether you are reporting to work in a courtroom, on the beach, or to fight a fire, you follow a dress code to perform in your environment. Athletes, musicians, and actors dress for their roles on the field, court, or stage.

As a college-preparatory school, we are preparing you for college and for your future careers. In accordance with our code of conduct, the Eight Pillars of Bowden, we require our faculty, students, and staff to respect an academic dress code. Dress with pride. Dress with the understanding that the academic experience during the school day is our job, a job that we are very proud to have.

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  • PRESENTABLE ACADEMIC WEAR: Monday, Tuesday, Thursday

    Monday, Tuesday, Thursday
    8:00 A.M. - 3:30 P.M.

    Acceptable Dress Includes:
    Pants or Bermuda length shorts, collared shirts, blouses or polos, skirts or dresses that are not too short. Ties and blazers are welcome but not required. Comfortable shoes or sneakers are recommended. On lab days in science classes be prepared to wear closed toe shoes and tie back long hair for safety precautions. Our goal is to provide students with an opportunity to dress for an academic environment without making anyone feel uncomfortable or singled out for their dress. 

    Wednesday, 8:45 A.M. - 12:45 P.M.

    Acceptable Dress Includes:
    Spirit wear includes t-shirts, polo shirts, or sweatshirts with a Cheshire Academy logo. Jeans without rips are acceptable dress on Spirit wear days.
  • FORMAL WEAR: Friday & Special Occasions

    Friday, 8:00 A.M. - 3:30 P.M.

    Acceptable Dress Includes:
    Formal wear includes a button-down white dress shirt or blouse, a Cheshire Academy tie (required for boys, optional for girls), a navy blue blazer with the Cheshire Academy patch, gray dress pants or skirt. A solid gray dress may be worn with the formal wear blazer.

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    Emma Gawronski ’14,
    Nicolina Lamberti ’14
    in girls formal wear.
    Thomas Cavaliere ’15
    in boys formal wear.

  • Dress Code Purchasing Information

    1. The Cheshire Academy School Store
    2. Flynn & O’Hara
      Customer Service: 800-441-4122
    3. Land’s End
      Preferred School Number: 900138876,     
      Customer Service: 800-469-222.       
      Order here. Instructions here.
    4. Paul’s Fine Clothing 
      Click here to download the order form.
  • Cheshire Academy Patches

    New incoming domestic students will receive their Cheshire Academy uniform patches via mail in July. International students will receive their patches when they arrive to campus.


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSION OFFICE: 203-439-7250
ADMISSION FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

List of 1 items.

  • The Student-Centered Private School in Connecticut.

    We put the unique needs of every student first. That’s why we offer a flexible program that allows students to mix academic course tracks with athletics and/or fine arts programs, according to their needs and interests. Students can stretch their intellectual boundaries by taking one of 20 advanced International Baccalaureate® Diploma Programme courses, or practice new skills by participating in a range of afternoon programs including; athletics, fine arts, and performing arts. We are also the only Connecticut private school to offer one-on-one student coaching through our Roxbury Academic Support Program.
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