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Get ready to step into a world of effortless charm with preppy dresses that capture the essence of classic style and modern flair. Whether you're heading to brunch with friends or a weekend getaway, these fresh new styles offer the ideal blend of elegance and everyday ease. Think crisp lines, playful patterns, and a touch of sophistication that takes you from beach to street in style. Discover your look with Tillys' great assortment of preppy dresses designed for those who love to make a statement while keeping it cool and comfortable.

$36.99
Now $9.97 (73% Off)

SALE!

A pink floral midi dress with a cinched scoop neckline, adjustable straps, and a leg slit.

$49.99
Now $31.48 (37% Off)

SALE!

A blue plaid maxi dress with a V-neckline, zipper closure, and a flowy silhouette.

$59.99
Now $23.98 (60% Off)

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A vibrant floral print dress with a smocked bodice and square neckline, made from 100% viscose.

$34.99

A blue gingham mini dress featuring a tie detail, adjustable straps, and a corset-like bodice.

$32.99
Now $12.39 (62% Off)

SALE!

A navy sleeveless bodycon dress with classic polo stripes, collared neckline, and button front placket.

$32.99
Now $12.39 (62% Off)

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A red sleeveless bodycon dress with classic polo stripes, collared neckline, and button front placket.

$73.60
Now $58.88 (20% Off)

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A light blue gingham mini dress with adjustable straps, ruched bust, and tiered flare skirt.

$60.80
Now $48.64 (20% Off)

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A black gingham cotton mini dress with a halter neck, open back, and button front detailing.

$70.40
Now $56.32 (20% Off)

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A brown plaid mini dress with a fold-over neckline, lace-up back, and cut-out detail.

$76.80
Now $61.44 (20% Off)

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A preppy black mini sweater dress with a V-neckline, layered collar, and pleated skirt.

$36.99

A red gingham slip dress with adjustable straps and embroidered details, crafted from a cotton-polyester blend.

$29.99
Now $9.97 (67% Off)

SALE!

A pink plaid slip dress with adjustable straps, V-neckline, and back zip closure.

$39.99
Now $12.48 (69% Off)

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A sleeveless tank dress with a textured pattern and scoop neckline, made from polyester and rayon.

$45.99

A breathable leopard print maxi dress with lace trim, adjustable straps, and built-in lining.

$36.99
Now $17.48 (53% Off)

SALE!

A medium wash denim dress with a button-front design and adjustable spaghetti straps.

$59.99
Now $24.48 (59% Off)

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A vibrant floral print dress with a V-neckline, short sleeves, and a smocked back in viscose.

$29.99
Now $11.98 (60% Off)

SALE!

A fitted black halter dress with ribbed construction and self-tie straps, made from rayon and nylon.

$78.99
Now $37.48 (53% Off)

SALE!

A cute off-the-shoulder butterscotch midi dress with ruffle hem, made from 100% viscose.

$79.99

A stylish black maxi dress with removable straps and metal logo trim, made from 100% cotton.

$36.99
Now $12.48 (66% Off)

SALE!

A lavender mesh slip dress with vibrant floral print, tiered ruffles, and adjustable spaghetti straps.

$34.99
Now $12.48 (64% Off)

SALE!

A dark blue lace tier slip dress with tied spaghetti straps and a smocked back for a chic fit.

$74.99
Now $39.97 (47% Off)

SALE!

A multi-colored floral midi dress with a V-neck, button front, and short sleeves, made of 100% viscose.

$32.99
Now $12.39 (62% Off)

SALE!

A vibrant pink floral tube dress with ruffle details and an elastic smocked waist for a flattering fit.

$45.99
Now $23.78 (48% Off)

SALE!

A cream sweater dress with bell sleeves and high neckline, made from soft rib knit fabric.