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What to wear on the first day of school


Dressing for your first day of school - especially if you’re attending a new school - can be stressful. But don't fret, we have five tips to make choosing what to wear on the first day of school easier.

1. Check the Dress Code

Most private schools like Cheshire Academy have dress codes that clearly outline what you are supposed to wear. Visit your school’s website or check out your Student Handbook to find information on the dress code. Make sure you are within the regulations of your school’s dress code, that’s the best first step!

2. Make sure your clothes fit properly

This seems like common sense, but sometimes we overlook this basic but important rule. The first day of school can be stressful, so spending the day tugging at a shirt that doesn’t fit right or dealing with pants that drag on the ground won’t make it any easier. Schools often have rules about wearing properly fitted clothing, too.

3. Wear comfortable shoes

Don’t wear brand new shoes that you’ve never worn before; you don’t want any surprises. Especially if you attend a boarding school like Cheshire Academy and have to walk from building to building across campus, you won’t want to deal with squeaky shoes, slippery soles or blisters. Don’t forget to make sure that your shoes are acceptable within the dress code, as many schools do not allow shoes like sneakers or flip flops.

4. Moderation is key

When you’re heading to school on the first day, you want to look your best, but don’t go overboard. Avoid wearing heavy perfume or cologne, as this can be distracting to those around you. Accessorize your look if you'd like, but stay simple. Some schools may have strict rules on the kinds of accessories allowed, so always keep this in mind.

5. Scope out the school’s photo albums and social media for examples

Private schools like Cheshire Academy regularly post photos of their students, so surfing the website can give you an idea of what other students wear. Do boys ever wear bow ties? A quick survey of Cheshire Academy photo albums will show that a few do! Plus, social media outlets are a great place to see photos of students during school activities. You could even post your look on Facebook or Instagram if you're feeling inspired!

If you’re still not sure what to wear, seek out another student to ask or call your Dean of Students for information. You’ll be sure to find someone who can answer your questions.

Good luck on your first day of school!

Post your first day of school outfit on Instagram with #CAfirstday and share your 'first day of school' outfit!

Stacy Jagodowski

Written by Stacy Jagodowski

Ms. Jago joined the Cheshire Academy community in August 2013 as the director of strategic marketing and communications. Prior to coming to Cheshire Academy, she spent six years working in communications offices at both colleges and private school, as well as five years in admission at both boarding schools and day schools.

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