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        Women's Preppy Dresses

        Dresses – Classic Preppy Style for Every Occasion

        At The Lucky Knot, we specialize in the best preppy dresses that are as versatile as they are vibrant. Our resort-inspired collection is full of colorful, nautical styles that bring a touch of fun and freshness to every day. Whether you’re headed to work, out for errands, on vacation, or just enjoying the weekend, we have the perfect dress to fit your plans—and your style. From timeless silhouettes to playful prints, these dresses will brighten your wardrobe and your mood. Polished, preppy, and effortlessly chic—your new favorite dress is here.

         

        Model in a green and blue tiered maxi dress with a tropical pattern. Also has a v-neck with a traditional collar and short sleeves Model in a green and blue tiered maxi dress with a tropical pattern. Also has a v-neck with a traditional collar and short sleeves
        Patty Kim Marni Maxi Dress - Peri Rococo Patty Kim
        $239.00
        Model twirling in a short, tiered dress with long sleeves and a v neck. The material is a beautiful light purple, with Sail to Sable's signature gold dot. Model twirling in a short, tiered dress with long sleeves and a v neck. The material is a beautiful light purple, with Sail to Sable's signature gold dot.
        Sail To Sable x The Lucky Knot Addison Dress - Hydrangea Sail to Sable
        $268.00
        Model in a blue and green patterned, knee length dress, with collar and contrasting cuff sleeves Model in a blue and green patterned, knee length dress, with collar and contrasting cuff sleeves
        Patty Kim Elizabeth Dress - Peri Rococo Patty Kim
        $238.00
        Sail to Sable Long Sleeve Tunic Flare Dress - Blue White Stripe Sail to Sable Long Sleeve Tunic Flare Dress - Blue White Stripe
        Sail to Sable Long Sleeve Tunic Flare Dress - Blue White Stripe Sail to Sable
        $198.00
        Model in a tiered midi dress with a ruched waist, flutter sleeves, and v neck. It has a beautiful blue, purple, metallic gold floral print, that is both subtle and stunning Model in a tiered midi dress with a ruched waist, flutter sleeves, and v neck. It has a beautiful blue, purple, metallic gold floral print, that is both subtle and stunning
        Sail to Sable Flutter Sleeve Midi Dress - Falling Violets Print Sail to Sable
        $288.00
        Model in a long blue ikat dress with ruching under the bust and flutter sleeves. Model in a long blue ikat dress with ruching under the bust and flutter sleeves.
        Sail to Sable Flutter Sleeve V-Neck Midi Dress - Blue Ikat Sail to Sable
        $248.00
        Model in courtyard wearing Gretchen Scott Fiesta Time Dress in White/Gold Model in courtyard wearing Gretchen Scott Fiesta Time Dress in White/Gold
        Gretchen Scott Fiesta Time Dress - White/Gold Gretchen Scott
        $199.00
        Chatham Eyelet Midi Dress Chatham Eyelet Midi Dress
        Chatham Eyelet Midi Dress THE LUCKY KNOT
        $89.00
        Model on boat wearing Gretchen Scott Fiesta Time Dress in White/Periwinkle Model on boat wearing Gretchen Scott Fiesta Time Dress in White/Periwinkle
        Gretchen Scott Fiesta Time Dress - White/Peri Gretchen Scott
        $199.00
        Model in a blue, long sleeved shift dress with a floral pattern and detailing at the collar, wrists, and bottom hem Model in a blue, long sleeved shift dress with a floral pattern and detailing at the collar, wrists, and bottom hem
        Sail to Sable Long Sleeve Classic Tunic Midi Dress - Sky Baroque Floral Sail to Sable
        $228.00
        Gretchen Scott Hope Dress - Periwinkle Gretchen Scott Hope Dress - Periwinkle
        Gretchen Scott Hope Dress - Periwinkle Gretchen Scott
        $199.00
        Woman wearing a blue knee-length shirt dress with a white tropical print, tie waist, and rolled sleeves with a green contrast cuff. Woman wearing a blue knee-length shirt dress with a white tropical print, tie waist, and rolled sleeves with a green contrast cuff.
        Patty Kim Elizabeth Dress - Sky Peacock Green Patty Kim
        $239.00
        Nantucket Ruffle Floral Maxi Dress - Blue Nantucket Ruffle Floral Maxi Dress - Blue
        Nantucket Ruffle Floral Maxi Dress - Blue THE LUCKY KNOT
        $108.00
        Model wearing a tiered maxi dress in a blue floral print with a ruched waist and flutter sleeves. Model wearing a tiered maxi dress in a blue floral print with a ruched waist and flutter sleeves.
        Sail to Sable x The Lucky Knot Flutter Sleeve Midi Dress - Baroque Floral Sail to Sable
        $288.00
        Model in a tiered midi dress with a ruched waist, sheer long sleeves, and v neck. It has a beautiful blue, purple, metallic gold floral print, that is both subtle and stunning Model in a tiered midi dress with a ruched waist, sheer long sleeves, and v neck. It has a beautiful blue, purple, metallic gold floral print, that is both subtle and stunning
        Sail to Sable x The Lucky Knot Katelyn Midi Dress - Falling Violets Print Sail to Sable
        $288.00
        Jude Connally Bailey Dress - Grand JC Key Cornflower Jude Connally Bailey Dress - Grand JC Key Cornflower
        Jude Connally Bailey Dress - Grand JC Key Cornflower Jude Connally
        $198.00
        Jude Connally Kristen Dress - Petite Rattan Cobalt Jude Connally Kristen Dress - Petite Rattan Cobalt
        Jude Connally Kristen Dress - Petite Rattan Cobalt Jude Connally
        $198.00
        Jude Connally Emerson Dress - Bamboo Rattan Cornflower Jude Connally Emerson Dress - Bamboo Rattan Cornflower
        Jude Connally Emerson Dress - Bamboo Rattan Cornflower Jude Connally
        $248.00
        Jude Connally Emerson Dress - Petite Rattan Navy Jude Connally Emerson Dress - Petite Rattan Navy
        Jude Connally Emerson Dress - Petite Rattan Navy Jude Connally
        $258.00
        Jude Connally Libby Dress - Bamboo Rattan Cornflower Jude Connally Libby Dress - Bamboo Rattan Cornflower
        Jude Connally Libby Dress - Bamboo Rattan Cornflower Jude Connally
        $228.00
        Jude Connally Libby Dress - Petite Rattan Navy Jude Connally Libby Dress - Petite Rattan Navy
        Jude Connally Libby Dress - Petite Rattan Navy Jude Connally
        $228.00
        Jude Connally Bailey Dress - Petite Rattan Cobalt Jude Connally Bailey Dress - Petite Rattan Cobalt
        Jude Connally Bailey Dress - Petite Rattan Cobalt Jude Connally
        $198.00
        Jude Connally Ginger Dress - Grand JC Key Cornflower Jude Connally Ginger Dress - Grand JC Key Cornflower
        Jude Connally Ginger Dress - Grand JC Key Cornflower Jude Connally
        $218.00
        Jude Connally Susanna Dress - Petite Rattan Navy Jude Connally Susanna Dress - Petite Rattan Navy
        Jude Connally Susanna Dress - Petite Rattan Navy Jude Connally
        $218.00
        Jude Connally Susanna Dress - Bamboo Rattan Cornflower Jude Connally Susanna Dress - Bamboo Rattan Cornflower
        Jude Connally Susanna Dress - Bamboo Rattan Cornflower Jude Connally
        $218.00
        Jude Connally Ginger Dress - Petite Rattan Cobalt Jude Connally Ginger Dress - Petite Rattan Cobalt
        Jude Connally Ginger Dress - Petite Rattan Cobalt Jude Connally
        $218.00
        Jude Connally Kristen Dress - Grand JC Key Cornflower Jude Connally Kristen Dress - Grand JC Key Cornflower
        Jude Connally Kristen Dress - Grand JC Key Cornflower Jude Connally
        $198.00
        Smiling model in front of a white wall with a plant in the corner in the Jude Connally Tess Midi Dress - Terrace Geo Border Navy. A midi, v neck, sleeveless, drawstring waist dress with a white, green, and navy geometric pattern Smiling model in front of a white wall with a plant in the corner in the Jude Connally Tess Midi Dress - Terrace Geo Border Navy. A midi, v neck, sleeveless, drawstring waist dress with a white, green, and navy geometric pattern
        Jude Connally Tess Midi Dress - Terrace Geo Border Navy Jude Connally
        $218.00
        Smiling model in the Duffield Lane Fleur Dress - Skinny Blue Seersucker. A midi length sundress with off the shoulder sleeves, with a very skinny seersucker pattern. Smiling model in the Duffield Lane Fleur Dress - Skinny Blue Seersucker. A midi length sundress with off the shoulder sleeves, with a very skinny seersucker pattern.
        Duffield Lane Fleur Dress - Skinny Blue Seersucker Duffield Lane
        $218.00
        Smiling model in front of a white wall with a plant in the corner in the Jude Connally Shari Dress - Wild Blossom Blue. A short dress with flutter sleeves and collar, with a blue, green, and navy floral pattern Smiling model in front of a white wall with a plant in the corner in the Jude Connally Shari Dress - Wild Blossom Blue. A short dress with flutter sleeves and collar, with a blue, green, and navy floral pattern
        Jude Connally Shari Dress - Wild Blossom Blue Jude Connally
        $218.00
        Pretty In Flamingo Maxi Pretty In Flamingo Maxi
        Pretty In Flamingo Maxi THE LUCKY KNOT
        $88.00
        Smiling model in the Isla Payal Amalfi Maxi - Blue Meadow. A maxi length blue floral dress, with flutter sleeves, v neck, and drawstring waist Smiling model in the Isla Payal Amalfi Maxi - Blue Meadow. A maxi length blue floral dress, with flutter sleeves, v neck, and drawstring waist
        Isla Payal Amalfi Maxi - Blue Meadow IslaPayal
        $248.00
        Savannah Pink Floral Maxi Dress Savannah Pink Floral Maxi Dress
        Savannah Pink Floral Maxi Dress Mable
        $128.00
        Front view of model in a hot pink sleeveless, knee length, knit dress Front view of model in a hot pink sleeveless, knee length, knit dress
        Lilly Pulitzer Stassi Knee Length Textured Scrunch Dress - Roxie Pink Lilly Pulitzer
        $148.00
        Model holding onto a rope on the water in the Coastal Blossom Midi Dress. A tiered maxi dress with tie straps and blue floral pattern on a white background Model holding onto a rope on the water in the Coastal Blossom Midi Dress. A tiered maxi dress with tie straps and blue floral pattern on a white background
        Coastal Blossom Midi Dress THE LUCKY KNOT
        $89.00
        Smiling model in a pink spaghetti strap mini dress. it has a thick lace eyelet overlay
        Lilly Pulitzer Shelli Eyelet Dress - Roxie Pink - Garden Party Eyelet Lilly Pulitzer
        $208.00
        Smiling model in the Lilly Pulitzer Dune Short Sleeve Dress - Rousseau Pink - Barefoot Beachcombers. A hot pink mini dress with short sleeves and a collar, with light blue beach motifs Smiling model in the Lilly Pulitzer Dune Short Sleeve Dress - Rousseau Pink - Barefoot Beachcombers. A hot pink mini dress with short sleeves and a collar, with light blue beach motifs
        Lilly Pulitzer Dune Short Sleeve Dress - Rousseau Pink - Barefoot Beachcombers Lilly Pulitzer
        $148.00
        Smiling model in the Lilly Pulitzer Verica Silk Maxi Dress - Rousseau Pink - Oversized Barefoot Beachcombers. A spaghetti strap, hot pink maxi dress with blue shell details Smiling model in the Lilly Pulitzer Verica Silk Maxi Dress - Rousseau Pink - Oversized Barefoot Beachcombers. A spaghetti strap, hot pink maxi dress with blue shell details
        Lilly Pulitzer Verica Silk Maxi Dress - Rousseau Pink - Oversized Barefoot Beachcombers Lilly Pulitzer
        $358.00
        Model in the Lilly Pulitzer Parigi Knit Skort Romper - Rousseau Pink - Oversized Barefoot Beachcomber. A hot pink, short sleeved romper with blue and white beach motifs Model in the Lilly Pulitzer Parigi Knit Skort Romper - Rousseau Pink - Oversized Barefoot Beachcomber. A hot pink, short sleeved romper with blue and white beach motifs
        Lilly Pulitzer Parigi Knit Skort Romper - Rousseau Pink - Oversized Barefoot Beachcomber Lilly Pulitzer
        $168.00
        Smiling model outside in the Cabana Life Seaside 1/4 Zip Sleeveless Sport Dress. A sleeveless, 1/4 zip neckline, mini dress with pockets with a blue and white geometric pattern Smiling model outside in the Cabana Life Seaside 1/4 Zip Sleeveless Sport Dress. A sleeveless, 1/4 zip neckline, mini dress with pockets with a blue and white geometric pattern
        Cabana Life Seaside 1/4 Zip Sleeveless Sport Dress Cabana Life
        $138.00
        Smiling model holding a glass of champagne in the Cabana Life Bubbly Short Sleeve Tiered Ruffle Dress. A short sleeved, tiered, v-neck dress that is white with blue floral pattern Smiling model holding a glass of champagne in the Cabana Life Bubbly Short Sleeve Tiered Ruffle Dress. A short sleeved, tiered, v-neck dress that is white with blue floral pattern
        Cabana Life Bubbly Short Sleeve Tiered Ruffle Dress Cabana Life
        $134.00
        Smiling model leaning against a pillar holding a glass of champagne in the Cabana Life Bubbly Sleeveless Tunic Cover Up. A sleeveless mock neck shift dress with blue flowers on a white background and royal blue trim around the neckline and bottom hem Smiling model leaning against a pillar holding a glass of champagne in the Cabana Life Bubbly Sleeveless Tunic Cover Up. A sleeveless mock neck shift dress with blue flowers on a white background and royal blue trim around the neckline and bottom hem
        Cabana Life Bubbly Sleeveless Tunic Cover Up Cabana Life
        $138.00
        Model in the Patty Kim Megan Dress - Green Foulards. A knee length dress with flutter sleeves and ruffles on the collar and bottom hem, and a tie waist Model in the Patty Kim Megan Dress - Green Foulards. A knee length dress with flutter sleeves and ruffles on the collar and bottom hem, and a tie waist
        Patty Kim Megan Dress - Green Foulards Patty Kim
        $229.00
        Woman wearing a sleeveless navy dress with a white geometric triangle pattern, deep V neckline with striped trim, and a flounced hem. Woman wearing a sleeveless navy dress with a white geometric triangle pattern, deep V neckline with striped trim, and a flounced hem.
        Duffield Lane Daisy Dress - Navy Flags Duffield Lane
        $189.00
        Model wearing the Patty Kim Megan Dress - Blue Foulards. a blue, knee length dress with a tie waist and flutter sleeves and collar. Model wearing the Patty Kim Megan Dress - Blue Foulards. a blue, knee length dress with a tie waist and flutter sleeves and collar.
        Patty Kim Megan Dress - Blue Foulards Patty Kim
        $229.00
        Smiling model in a mini pink linen dress, with a shirt collar, buttons down the front, and short puff sleeves Smiling model in a mini pink linen dress, with a shirt collar, buttons down the front, and short puff sleeves
        Dolce Cabo Magnolia Dress - Pink Dolce Cabo
        $154.00
        Model in a white dress with a tortoise shell belt buckle Model in a white dress with a tortoise shell belt buckle
        Dolce Cabo Francesca Midi - White Dolce Cabo
        $134.00
        Lilly Pulitzer Theodorah Sweater Dress Bluette Metallic Marl Lilly Pulitzer Theodorah Sweater Dress Bluette Metallic Marl
        Lilly Pulitzer Theodorah Sweater Dress Bluette Metallic Marl Lilly Pulitzer
        $218.00