Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

Vacation Dresses & Outfits for Effortless Getaways

Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.

Easy, Packable Styles

Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.

Day-to-Night Versatility

Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.

Resort & Beach Essentials

Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.

Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.

  • Tropical Energy Strapless Crop Top

    Bring the energy to your destination getaway in this tropical crop top, designed with a sleek strapless neckline and fitted hem. Pair it with the matching skirt.

    Fit & Features

    • Tropical print, mesh fabric, soft knit stretchy lining
    • Strapless neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Tropical Energy High-Rise Midi Skirt

    Style Number/Barcode: 06001-000053

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: TAN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Basic Essential Ribbed Knit Midi Dress

    This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Form-hugging fit
    • Side slit, midi-length hem
    • Double-lined rib knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4961

    Category Name: Vacation Looks

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Babe Halter V-Neck Corset Crop Top

    You'll be the cutest babe in this room in this sleeveless corset crop top! Featuring a flattering halter V-neckline, supportive underwire bust, and hidden front hook and eye fasteners, with figure-enhancing flexible boning while the cropped hem adds a touch of playfulness. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants

    Fit & Features

    • Woven fabric, sewn-in knit lining, no stretch
    • Halter V-neckline
    • Underwire bust
    • Hidden front hook and eye fasteners
    • Flexible boning
    • Back zipper and hook-eye closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2542

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • It's The Tequila Talking Graphic Tee

    Live your best life with this fun graphic tee that says it all! It features a crew neckline, short sleeves, a center script that reads "It's The Tequila Talking," and a cropped fit with a cute knot-front detail. Complete the look with distressed denim and hoop earrings.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Script that reads "It's The Tequila Talking"
    • Cropped, form-hugging fit
    • Knot-front detail
    • Jersey knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1095

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Romance Sleeveless Lace-Up A-Line Midi Dress

    Designed for a modern-day romance, this sleeveless woven midi dress is perfect for day dates! The sweetheart ruched neckline and adjustable straps are flattering, while the lace-up design cinches your waist for a beautiful silhouette. The front slit adds a touch of allure to this A-line midi-length dress. Complete the look in strappy wedges.

    Fit & Features

    • Texture woven fabrication with a woven lining
    • Sweetheart neckline, ruched bust, dainty lace trim
    • Adjustable straps
    • Lace-up waist, stretchy smocked back
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5722

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Petals and Plans Floral Lace-Up Maxi Dress

    For date nights, rooftop drinks, or weddings, this floral maxi dress is perfect for every event! The curve-hugging fit, flirty slit, and open lace-up back effortlessly flatters your figure and makes heads turn.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Lace-up open back
    • High front slit
    • Curve-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4160

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L, XL

  • Dressing For Sunshine Eyelet Lace Mini Dress

    The perfect eyelet lace mini dress for sunny days! It features adorable puff short sleeves, a sweetheart neckline, a front bust ruched drawstring, and a bodycon silhouette. The eyelet lace fabric includes a knit lining and offers moderate stretch. Complete the look in this mini dress with cute sandals.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neckline
    • Front bust ruched drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5118

    Category Name: Vacation Looks

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twice The Love Rib Knit Midi Skirt

    Dive into cozy rib knit love with this midi skirt! Perfect for everyday styling, this midi skirt features a high-rise elasticized waist and curve-flaunting bodycon silhouette and a side slit that shows some skin. Complete the look with the matching top.

    Shop Matching Top: Twice The Love Rib Knit Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0937

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Icon Flat Jelly Slide Sandals

    Playful jelly slides that elevate the iconic style you know and love for spring to summer! These fashion sandals feature a sleek square toe, a woven single band, and a comfortable flat sole on jelly material. Complete the look with a statement tote bag for a beach day or outdoor dinner party! 

    Fit & Features

    • Square toe
    • Woven single band
    • Flat sole
    • Slide on-and-off styling
    • Jelly material
    • Runs true to size

    Style Number/Barcode: 07404-1196

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Shell-Trim Straw Cowboy Hat

    Capture the coastal cowgirl trend with this shell-trim cowboy hat perfect for breezy days by the water! Crafted with a woven straw material, it features a structured top, a wide brim with curved sides, and a seashell-beaded accent trim and long neck strap for those beachy vibes. Includes an interior elastic band. Style with a crochet top and jean shorts.

    Fit & Features

    • Woven straw material
    • Structured top
    • Wide brim, curved sides
    • Shell-beaded accent trim and neck strap
    • Interior elastic band

    Style Number/Barcode: 07302-1612

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Sweet Ruffled Eyelet Lace Mini Dress

    Make your sweet impression in this eyelet lace mini dress detailed with ruffled straps and an adorable ruched neckline. The form-hugging fit will highlight your stunning curves.

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Sweetheart neckline, ruching
    • Ruffled straps
    • Mini-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6002

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • A Way With Lace V-Neck Mini Dress

    Let this lace mini dress speak your favorite language, romance! The short dress features a sleeveless V-neckline, spaghetti straps, a bodycon silhouette, and a sheer lace overlay with a sewn-knit lining. Complete the look in rhinestone mules for a wedding shower or birthday brunch!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Sheer lace overlay, sewn-in knit lining
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5088

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Star Of The Show Crochet Sweater

    An effortless crochet sweater for layering or styling alone! It's designed with a star front design that adds a trendy touch and a relaxed fit for comfort. 

    Fit & Features

    • Sheer crochet fabric
    • Crew neck
    • Relaxed long sleeves
    • Front star design
    • Relaxed fit hem
    • Runs true to size

    Style Number/Barcode: 06005-000049

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Winged Goddess Butterfly Rhinestone Mules

    Give your feet goddess vibes in these faux leather mules perfect for glam brides or cocktail soirees! They feature a square toe, a strappy design with butterflies and rhinestone embellishments, and a low-block heel. Complete the look with a sparkly clutch purse.

    Fit & Features

    • Square toe
    • Strappy design
    • Butterflies with rhinestone embellishments
    • Low block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4204

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Admiring Style Strapless Ruffle High Low Denim Dress

    Prepare for plenty of admiring stares when you're in this stylish denim strapless dress! This cute and casual dress features a sweetheart neckline and form-hugging fit, accentuating your curves in all the right places. The patchwork seam detailing adds a touch of unique style, while the high-low ruffled hem adds a playful and flirty element. Complete the look in platform shoes and sunnies!

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffle high low hem
    • Runs true to size

    Style Number/Barcode: 05102-5574

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Effect Abstract Cowl Halter Crop Top

    Printed to perfection in a flattering halter silhouette, this crop top boasts a sultry cowl neckline and an open back to show some skin! Pair with the matching pants.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Cowl halter neckline, tie straps
    • Open back
    • Fitted crop hem
    • Runs true to size

    Shop The Matching Pants: Sultry Effect Abstract Wide-Leg Pants

    Style Number/Barcode: 06001-000107

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Part of a Set
  • Dial B For Basics Square Neck Mini Dress

    Dial B for this basic mini dress that'll inspire all your fashion-forward looks! It features a sleeveless square neckline, sleek bungee spaghetti straps, a form-hugging silhouette, and a mini-length hem. The double-line buttery knit fabric offers a seamless design and plenty of stretch. Style with a minimalistic necklace and earrings to inspire your day or night outfit! 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Form-hugging silhouette
    • Mini-length hem
    • Double-lined buttery knit fabric, moderate stretch
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 05102-5134

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Vibes Bow Back Woven Crop Top

    This airy woven crop top will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric, it features a sweetheart neckline with ruching at the bust, thin tank shoulder straps, an alluring open back with the cutest tie-back bow design, and a cropped hem with a form-hugging fit for a snatched silhouette. Style with the matching midi skirt for a fabulous 'fit.

    Shop Matching Fuchsia Bottoms: Sunny Vibes Woven Wide-Leg Pants
    Shop Matching Orange Bottoms: Sunny Vibes High Slit Woven Midi Skirt

    Fit & Features

    • Woven fabric with front knit lining, minimal stretch
    • Sweetheart neckline, ruched bust
    • Thin tank straps
    • Open-back, tie-back bow design
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2413

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: S, M

  • Boho Style Crochet Hanky Hem Halter Top

    Channel that trendy boho-chic style with this crochet knit halter top! The high halter neckline leads to a bold open-back design with cross-back tie straps offering an adjustable fit. The cropped asymmetric hanky hem will create a snatched look on the form-hugging silhouette. Pair with high-rise jeans and strappy sandals for a casual summer vibe.

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Halter neckline
    • Open back with cross-back tie straps
    • Asymmetric hanky hem
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06005-1958

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Cute Eyelet Lace Mini Dress

    Achieve an effortless pretty and cute style in this eyelet lace mini dress for your casual dates or strolling downtown with the girls! The dress features adorable puff short sleeves, a ruffle trim sweetheart neckline with a front bust tie, a bodycon fit, and side ruching with an adjustable tie. Complete the look in trendy flat sandals.

    Fit & Features

    • Puff short sleeves
    • Ruffle trim sweetheart neckline
    • Front bust tie
    • Bodycon silhouette
    • Side ruching with adjustable tie
    • Mini-length hem
    • Eyelet lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4912

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed And Cute Polka Dot Chiffon Skater Dress

    Envoke a charmed and cute style in this polka dot skater dress perfect for showers or graduates! Show off your curves with the sweetheart neckline and skater silhouette, while adding a touch of cuteness with the short puff sleeves. The tie-back adds a flirty detail and the short-length hem is perfect styling with trendy sneakers for a casual vibe.

    Fit & Features

    • Polka dot, chiffon fabric, woven lining, no stretch
    • Sweetheart neckline
    • Padded bra cups
    • Back zipper hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3289

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Queen Tropical Floral Mesh Maxi Skirt

    Slay your next vacay in this gorg tropical floral mesh maxi skirt with a mini-length lining and a high-cut side slit. Style with the matching crop top for a sultry vibe!

    Shop Matching Top: Vacay Queen Tropical Floral Mesh Tie-Front Top

    Fit & Features

    • Sheer mesh fabric with mini-length knit lining, high stretch
    • Large tropical floral print
    • Mid-rise waist
    • Hip-hugging fit
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000030

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Barely Blushing Floral Mini Dress

    Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!

    Fit & Features

    • Floral print, burnout texture, mesh fabric, stretchy knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000165

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • All The Cozy Feels Faux Fur Knit Beanie

    Keep your winter 'fit cozy with this adorable knit beanie! It features a ribbed fold-over hem, a cable knit design, an ultra-plush faux fur lining to keep you warm, and a top fuzzy faux fur pom detail. Style this cute beanie with your favorite sweater.

    Fit & Features

    • Ribbed fold-over hem
    • Cable knit design
    • Soft faux fur lining
    • Faux fur pom

    Style Number/Barcode: 07302-0988

    Category Name: Vacation Looks

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale