FREE SHIPPING on orders over $59* details

Selecting an option from this dropdown will refresh the page.
Selecting an option from this dropdown will refresh the page.

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 $20.97 (43% Off)

SALE!

A blue rayon slip dress with an allover floral print, lace trim, and adjustable straps.

$54.99
Now $29.97 (45% Off)

SALE!

A flowy mini dress with a floral print, front cutout, and adjustable straps in 100% viscose.

$74.99
Now $49.97 (33% Off)

SALE!

A pink strapless midi dress with a smocked bodice and flowy fit, made from 100% viscose.

$48

A flattering black mini dress with short sleeves and center ruching, made from 95% cotton and 5% spandex.

$75.20

A light blue, 100% cotton denim mini dress with adjustable straps and pockets for a relaxed, casual look.

$46.40

A girly black mini dress with elegant bow detail and flattering ribbed fabric blend.

$98

A navy floral slip dress with a sweetheart neckline, adjustable shoulder ties, and double-layered mesh design.

$76.80

A beige crochet mini dress perfect for summer, made from 50% cotton and 50% polyester.

$54.40

A pink mini dress with an open back, asymmetric hem, and delicate lace bow details.

$67.20

A white cotton babydoll mini dress with lace trim and ribbon detail for a feminine touch.

$57.60

A light pink ribbed mini dress with frill trim and stitched cup detail, made of polyester and spandex.

$54.40

A versatile black off-shoulder ribbed midi dress made from 95% polyester and 5% spandex.

$52.80

A fun and flirty purple mini dress with gathered detailing and shiny polyester-spandex fabric.

$62.40

A trendy beige strapless maxi dress in ribbed fabric with a flower print, made of polyester and spandex.

$54.40

A strapless yellow mini dress with a removable flower pin and cascading ruffles, made of polyester-spandex.

$78.40

A white embroidered cotton mini dress with ruffle and ribbon detailing, perfect for summer plans.

$54.40

A fun and flirty red mini dress with a striped pattern, ruffle hem, and gathered detailing.

$65.60

A light blue off-shoulder mini dress with ruffle detailing and lined lace fabric, perfect for summer.

$64

A playful navy mini dress with a bubble skirt and adjustable straps in ribbed polyester-spandex blend.

$64.99
Now $32.97 (49% Off)

SALE!

A multi-colored mini dress with flutter sleeves, smocked back, and V-neckline in crinkle viscose.

$70.40

A light pink mini dress with adjustable straps and a delicate ruffle design, made from polyester-spandex.

$52.80

A strapless beige mini dress with chic lace fabric and an eye-catching asymmetric hemline.

$64.99
Now $26.97 (59% Off)

SALE!

A black mini dress with floral print, tie-front chest panels, and a smocked back for comfort.

$51.20

A chic black mini dress with lace trim, adjustable straps, and comfortable ribbed fabric.

Preppy Dresses

When it comes to summer style, preppy dresses are the go-to for anyone looking to channel that effortless, sun-kissed vibe with a hint of classic charm. June days call for easy, breezy outfits that transition seamlessly from afternoon picnics to sunset dinners, and nothing does this better than a cute preppy dress. Whether you’re heading out for a day on the boardwalk, catching up with friends over iced coffee, or planning a weekend getaway, these dresses bring together crisp lines, playful prints, and polished details that just feel right for the season. The beauty of preppy dresses lies in their versatility—think lightweight fabrics that keep you cool, subtle pleats that move with you, and silhouettes that flatter without ever feeling fussy. They’re perfect for making a statement at summer events or simply adding a little extra polish to your everyday routine. If you’re searching for a preppy dress near me, it’s all about finding those fresh styles that match your personality and fit your plans, whether that means a sporty collar for tennis club vibes or a flirty ruffle for brunch with your crew.

Gifting a preppy dress is always a win, especially for grads, birthdays, or just-because surprises. There’s something undeniably special about unwrapping a new favorite—one that feels both put-together and playful, ready for everything from family photos to spontaneous adventures. These dresses preppy enough to impress at summer parties, yet relaxed enough for a stroll along the beach, make them a thoughtful gift for anyone who loves to mix timeless style with a dash of fun. For those building a summer wardrobe, consider how a preppy dress can be styled in endless ways: layered over a simple tee for a nod to ‘90s cool, paired with crisp sneakers for a day of exploring, or dressed up with a woven bag and sandals for an evening out. The right accessories—think straw hats, pearl barrettes, or a swipe of tinted lip balm—can transform your look and keep things feeling fresh and current. And if you’re all about coordination, don’t miss out on matching your dress with a pop of color from your favorite Preppy T Shirts for those laid-back, mix-and-match moments.

Summer is the perfect time to experiment with new fits and discover cute preppy dresses that reflect your unique style. Maybe you’re drawn to pastel hues and classic stripes, or maybe bold checks and playful patterns are more your thing—either way, preppy dresses are all about expressing confidence and individuality. They work for every vibe, from campus hangs to rooftop gatherings, and make getting ready feel like less of a chore and more of a treat. When shopping for the perfect preppy dress, pay attention to details like breathable fabrics, adjustable straps, and pockets (because who doesn’t love a dress with pockets?). These thoughtful touches can make all the difference when you’re out and about, soaking up the sun or dancing under the stars. Whether you’re a longtime fan of the preppy look or just starting to explore this classic-meets-modern style, there’s no better time than now to find that dress that feels like it was made for you. From spontaneous road trips to backyard BBQs, let your preppy dress take center stage and bring a little extra sunshine to every summer moment.