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Preppy Dresses

3 products

Preppy Accessories

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3 products

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Whispering Vines Maxi Dress

Whispering Vines Maxi Dress

$148.00

Burnished Gold

Tempest

2 colors

2 colors

Charlie Mini

Charlie Mini

$60.00

Coconut Milk Combo

Vivid Green Combo

Fallen Rock Combo

Navy Combo

4 colors

4 colors

Good Feels Ruffle Long-Sleeve Mini

Good Feels Ruffle Long-Sleeve Mini

$70.00

Green Haze

Yellow

Coconut Milk

Salsa

8 colors

8 colors

1 1

Preppy Dresses: Mini To Maxi Styles

Free People’s preppy dresses mix structure and softness in a way that feels both playful and intentional. Expect classic collars, subtle pleats, and clean lines - made to wear with a button-up or thrown on loose. Pair one with crew socks and Mary Janes for a nod to school-uniform energy, or layer under a relaxed blazer for something a little more pulled together. These dresses are equal parts polish and ease, with enough versatility to move from weekday errands to weekend plans. A fresh take on a familiar shape, made to be styled your way.