10 Back-to-School Outfits To Start The 2025 Fall Semester

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5. Move over Blair Waldorf,

After a full Coastal Grandmother summer by the beach and the tennis courts, you can bring the preppy energy to school by draping a sweater over your shoulders and wearing pleated skirts. Pretty and preppy is where it’s at with this double-layer pleated skirt. It’s fun and twirly, but it’s not the shortest skirt, so it’s OK to wear to most schools.