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.

  • Cute Vibes Flower-Detail Espadrille Wedges

    You'll love the cute vibes of these flower-detail espadrille wedges! Designed with a trendy espadrille wedge sole, they feature a closed almond toe made with a denim-like material and an adorable flower cutout design perfect for the summer season. They have a partially closed back and straps that lace up the leg with a tie closure for a fabulous look. Style with your fave sundress for a weekend party!

    Fit & Features

    • 3.5" Wedge heel
    • Espadrille sole
    • Closed almond toe
    • Denim-like material, flower cutout design
    • Partial closed back, lace-up straps with tie closure
    • Padded faux leather insole
    • Runs true to size

    Style Number/Barcode: 07406-0351

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High-Rise Straight Cropped Jeans by Windsor Denim

    Serve major style in these fabulous straight cropped jeans by Windsor Denim! They feature a flattering high-rise waist, a straight-leg silhouette, knee destruction accents, and a front cut-off style cropped hem. The medium-wash denim fabric offers a moderate stretch for comfortable wear. Complete the look in a cute corset top for a casual dinner!

    Fit & Features

    • High-rise waist
    • Straight-leg silhouette, knee destruction accents
    • Front cut-off cropped hem
    • Front button, hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium-wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0416

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: MEDIUM, DENIM

    Available Size: 11, 13

  • Tropical Vibes High Slit Wrap Maxi Skirt

    Give off major tropical vibes whether you're jet-setting to a dreamy oasis or headed to a weekend getaway in this printed maxi skirt! The stretchy knit fabric showcases a bold contrasting tropical print for a stylish allure, and includes a built-in knit brief for coverage. The skirt features a high-rise elasticized waist, a wrap-front design creating a sultry high slit, and a flowy A-line fit on the maxi-length silhouette. Pair with a basic tank top and strappy sandals. 

    Fit & Features

    • Stretchy knit fabric, built-in knit brief
    • Tropical print
    • High-rise elasticized waist
    • Wrap-front design, high slit
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 06501-0966

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Here To Stay Short Sleeve Tie Front Crop Top

    This short sleeve crop top is here to stay in your weekly lineup! Its dual tie front closures and cropped hem add a playful touch, while the scoop neckline with contrast trim and stretchy rib knit fabric provides a flattering fit. Complete the look in high-rise jeans and sandals!

    Fit & Features

    • Stretchy rib knit fabric
    • Contrast trim scoop neckline
    • Dual tie-front closures
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06202-0470

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Presence Floral Lace Trim Crop Top

    Charm them with your pretty presence in this floral lace trim crop top! The airy sheer mesh fabric is detailed with a blooming floral print for the sweetest vibes. The top features a sleeveless V-neckline, spaghetti straps, a dainty lace trim in a criss-cross design, ruffled overlays for a flirty flair, and a cropped hem. Style with high waist denim shorts and slip-on sandals for casual weekend plans.

    Fit & Features

    • Floral print
    • Stretchy sheer mesh fabric, knit top lining
    • V-neckline, spaghetti straps
    • Lace trim
    • Ruffled overlays
    • Cropped hem, lettuce edge trims
    • Runs true to size

    Style Number/Barcode: 06001-5290

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Of All Ribbon Bow Bodycon Mini Dress

    You'll be the cutest of all in this bodycon mini dress out on dates or brunch! Crafted from a woven fabric lined with stretchy knit, this dress features a flattering square neckline and a satin ribbon bow that adds an elegant touch. The bodycon silhouette hugs your curves beautifully, while the mini-length hem gives a playful and flirty vibe. Complete the look in sandals and sunnies!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Square neckline
    • Satin ribbon bow
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5655

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fantastic Sparkle Rhinestone Strappy Flat Sandals

    Rhinestone-embellished straps boast a fantastic sparkle to these glam sandals! They feature an almond toe, a strappy design, and a flat faux leather sole with rhinestone embellished trim for extra shimmer. Complete the look with a luxe purse for any occasion!

    Fit & Features

    • Flat faux leather sole, rhinestone embellished trim
    • Almond toe
    • Rhinestone embellished strappy design
    • Runs true to size

    Style Number/Barcode: 07404-1194

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Attitude Three-Pack Hoop Earrings Set

    Give off a glam attitude with this elevated hoop earrings set! It features three pairs of small hoop earrings with a chic three-row sphere design, a sleek two-row classic design, and a trendy five-row textured design. Includes post-back closures. Style this set with a layered chain necklace.

    Fit & Features

    • Three-pack small hoop earrings set
    • Three-row sphere design
    • Two-row classic design
    • Five-row textured design
    • Post-back closures

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-1975

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Day Ruffled Ditsy Floral Skater Dress

    You'll love every moment spent in this ditsy floral skater dress! The square neckline and spaghetti tie straps add a flirty touch, while the stretchy smocked bodice ensures a comfortable fit. With a playful ruffled skater silhouette and a mini-length hem, this dress is perfect for any occasion. Complete the look in wedges.

    Fit & Features

    • Ditsy floral print, woven fabric lined with knit
    • Spaghetti tie strap
    • Square neckline
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5425

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Chic Off-The-Shoulder A-Line Mini Dress

    Elevate any casual day in this off-the-shoulder mini dress! This stunning dress features a twisted bust accent for a trendy touch, an A-line silhouette, and a mini-length hem that creates a flattering fit on the smooth knit-lined fabric. Complete the look with luxe earrings for a dinner party!

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Off-the-shoulder neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5755

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Flair High Slit Ditsy Floral Knit Midi Dress

    Bring the sweet flair to date night in this high slit ditsy floral midi dress! The all-over ditsy floral print on the stretchy knit fabric is the perfect amount of sweetness with the sultry details of the mid-length dress. The sleeveless scoop neckline features a tie-front at the bust for a cute touch, spaghetti straps, an alluring thigh-high side slit to showcase some leg, and a slim-fit silhouette to showcase your figure. Style this midi dress with a faux leather jacket and heels!

    Fit & Features

    • Ditsy floral print, stretchy knit fabric
    • Sleeveless scoop neckline with bust tie
    • Spaghetti straps
    • Thigh-high side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5485

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Breeze Tropical Cutout Slit Maxi Dress

    Feel the island breeze in this tropical maxi dress while on vacation!  With a square neckline, spaghetti straps, and a form-hugging fit, this maxi dress is perfect for a day in the sun. The cutout bodice and high front slit add a touch of playfulness to your island look. Complete the look with sandals.

    Fit & Features

    • Tropical palm print, smooth stretchy knit fabric, sewn-in knit lining
    • Square neckline
    • Spaghetti straps
    • Cutout bodice, high slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5670

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy And Cool Twill Layered Hoodie Jacket

    Stay cozy and cool this season with this trendy crop jacket as a stylish layer perfect for chill nights! With long sleeves, snap-button cuffs, and a collar neckline, this jacket provides both warmth and style. The front snap-button-up closures and flap pockets add functionality, while the fleece-lined zip-up hoodie gives an extra layer of warmth. Complete the look with cute platform sneakers.

    Fit & Features

    • Twill woven fabric
    • Collar neckline
    • Front snap-button up closures, flap pockets
    • Cropped length
    • Fleece-lined zip up hoodie layer
    • Runs true to size

    Style Number/Barcode: 06204-1832

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L, XL

  • Wish On A Rhinestone Starfish Straw Flat Sandals

    Step into summer with these playful straw flat sandals. Featuring a round toe and wide strap adorned with rhinestone starfish and decor, you'll feel like a mermaid strolling on the beach! Complete the look with sunnies.

    Fit & Features

    • Flat sole
    • Round toe
    • Rhinestone embellished starfish and decor
    • Straw with metallic woven threads material
    • Runs true to size

    Style Number/Barcode: 07404-1230

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Aesthetic Five-Pack Bracelet Set

    The bracelet set features five bracelets with varying chic designs including a sleek snake chain, a trendy disc chain, a dainty paperclip chain accented with beading and faux pearls, a flat chain, and a classic paperclip chain. Style with hoop earrings.

    Fit & Features

    • Five-pack bracelet set
    • Snake chain
    • Disc chain
    • Dainty paperclip chain with beading and faux pearls
    • Flat chain
    • Paperclip chain
    • Adjustable lobster clasp closures

    Style Number/Barcode: 07003-0571

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sensational Match Bodycon Midi Skirt

    Make a sensational impression in this bodycon midi skirt on vacay or brunch! Pair with the matching top to complete the cute look.

    Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

    Fit & Features

    • Smooth stretchy double-lined knit fabric
    • High-rise waist
    • Side ruched seams
    • Center back slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000021

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Fave High Slit Maxi Dress

    Show off effortless style in this breezy gauze maxi dress designed with a smocked waist, high front slit, and flowy A-line silhouette. Perf for summer parties, pair with espadrille sandals.

    Fit & Features

    • Gauze woven fabric, stretchy knit lining
    • Sleeveless V-neckline, spaghetti straps
    • Open cross-back tie-back design
    • Smocked high waist
    • Tiered design, thigh-high front slit
    • Maxi-length hem, flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000121

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Breeze Ruffled Eyelet Maxi Skirt

    Spring into the new season in this eyelet maxi skirt for vacations or weekend fun! Featuring a flattering high-rise elasticized waist, this skirt will keep you feeling cool and confident. The tiered ruffled silhouette adds a touch of charm, while the maxi-length hem and eyelet lace fabric offer a romantic and airy look. Complete the look with the matching top.

    Shop Matching Top: Spring Breeze Sweetheart Tie Eyelet Crop Top

    Fit & Features

    • Eyelet lace fabric, stretchy shorts lining
    • High-rise elasticized waistband
    • Tiered ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 06503-1152

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Cool Mid-Rise Camo Cargo Shorts

    These effortlessly cool camo cargo shorts feature a mid-rise waist paired with a mid-thigh length relaxed fit. The cargo-style side pockets add some trendy edge to the casual silhouette.

    Fit & Features

    • Camo-printed cotton woven fabric, no stretch
    • Mid-rise waist with belt loops
    • Hidden front zipper with button closure
    • Two front pockets, two cargo side pockets, two faux back pockets
    • Mid-thigh length, relaxed fit
    • Shorts in size small have a 10" front rise with an 8" inseam
    • Runs true to size

    Style Number/Barcode: 06303-0289

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Time Tropical Floral Mesh Maxi Dress

    Get ready to be on island time in this gorg tropical floral mesh maxi dress perf for vacay. Featuring a strapless neckline and high side slit, style with heels.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large tropical floral print
    • Strapless straight neckline
    • High-cut side slit
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000102

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Posture Tie Back Floral Chiffon Skater Dress

    Radiate sunshine energy in this effortless floral chiffon skater dress perfect for graduation, brunch, and any dressy occasion! The sweetheart neckline and adjustable spaghetti straps provide a flattering fit, while the tie-back design adds a unique touch. The skater silhouette and ruffled short-length hem give you a playful look, adorned with a beautiful floral embroidered pattern! Complete the look with simple earrings.

    Fit & Features

    • Floral embroidered pattern
    • Chiffon fabric with woven lining
    • Adjustable spaghetti straps, tie-back design
    • Sweetheart neckline
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3246

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Staple Faux Fur Ankle Booties

    Fit & Features

    • Flat sole
    • Ankle-fit
    • Almond toe
    • Faux suede exterior
    • Faux fur lined insole
    • Runs true to size

    Style Number/Barcode: 07408-0114

    Category Name: Vacation Looks

    Price: $28.90

    Availability: Out of Stock

  • Love Game Plunge V-Neck Bubble Skater Dress

    Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.

    Fit & Features

    • Poplin woven fabric, sewn-in knit lining
    • Plunge V-Neckline
    • Short ruffled bubble sleeves
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2935

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Glam Slip-On Clogs

    Fit & Features

    • Faux fur material
    • Closed round toe
    • Buckle strap detail
    • Slip-on design
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07405-0190

    Category Name: Vacation Looks

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Sale