Ask Preppy Girl – First Day of School Outfit

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Hello Preppy Girl,

I am an incoming freshman at a private school in Massachusetts. This school is all about preppy and some of the earliest preps attended, so I really want to dress to impress on the first day. Do you have an suggestions of what to wear. I want to have a cute outfit, but like any other freshman, I do not want to stick out. I love your blog so much and I really trust your opinion.

Thank you so much!
– Cute Chameleon

Dear Cute Chameleon,
Congratulations on the new school. The first day of school can be so stressful! Its always smart to have a cute outfit or two picked out a few days in advance. One of my favorite classic standbys is a casual neutral skirt paired with a long sleeved button down shirt. If it is a warm day, roll the sleeves up to the elbows (check out the models on J. Crew’s web site). If it’s a cool day, wear a long cardigan sweater in a bright color like pink, navy blue, or green. On your feet wear TOMS or a cute pair of flats. I would avoid flip-flops unless they are allowed. If you want to go sleeveless make sure it is allowed by the dress code. A flowy blouse with a pair of capris and flats is another great option. Consider using a preppy tote bag to carry your books instead of a book bag. On the first day of school you want to look friendly and approachable. Wear minimal jewelry, a pair of pearl studs, a bracelet or two, and a great smile. Make sure to take mental notes of what everyone is wearing, each private school has their own trends. Then you will have a better idea of the campus culture and what to buy.

I hope you have a great first day of school!
– P.G.

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