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.

  • Beautiful Bliss Floral Sequin Mesh Babydoll Dress

    Get swept up in the beauty of this babydoll dress perfect for brides-to-be, wedding showers, and dressy soirees! The sheer 3/4 length puff sleeves and square neckline add a touch of romance, while the babydoll silhouette and short hem create a playful and flirty look. The floral embroidery and sequins on the sheer mesh overlay add a touch of whimsy to this stunning dress. Complete the look with a chic ring set and heels!

    Fit & Features

    • Sheer mesh overlay line with woven fabric
    • Floral embroidery, sequin embellishments
    • Back zipper and hook-eye closure
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3357

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Sparkle Large Hoop Earrings

    Give off a stunning sparkle when these hoops catch the light! These hoop earrings feature beautiful crystal-like details to top off all your looks with a bit of bling. Topped with post-back closures for easy wear. Style these sleek hoops with a chic bodysuit and high waist jeans for an effortlessly put-together look.

    Fit & Features

    • Large hoop design
    • Cyrstal-like details 
    • Post-back closure

     

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

    Style Number/Barcode: 07001-0105

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Here To Slay One-Shoulder Cutout Knit Crop Top

    This iconic crop top was here to stay and slay your 'fits! Made with a stretchy ribbed knit fabric, it features an asymmetric one-shoulder neckline with a tank strap, a trendy twist-front design and sultry center bust cutout, and a cropped hem with a form-hugging fit for a snatched look. Style with high-rise jeans and sneakers for a cute and casual vibe!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Asymmetric one-shoulder neckline, tank strap
    • Twist-front design
    • Bust cutout
    • Cropped
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1950

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Right Impression V-Neck Floral Ruffle Skater Dress

    A cutie like you will always make the right impression in this floral skater dress on dates or at brunch!  Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.

    Fit & Features

    • Floral print, chiffon fabric with woven lining, no stretch
    • V-neckline, V-cut back with spaghetti strap tie
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-2894

    Category Name: Vacation Looks

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artful Drama Floral Open Back Maxi Dress

    Serve artful drama in this halter maxi dress featuring a draped cowl neckline, sultry open back, and a watercolor-inspired floral print. Made for cocktail receptions, weddings, and statement entrances into parties.

    Fit & Features

    • Watercolor floral print, mesh-lined fabric, stretchy
    • Cowl halter neckline, tie closure
    • Open back with tie closure
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000690

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: S, M, L

  • Stunning Summer Daze Strappy Block Heels

    Put them all in a daze with the chic details of these stunning strappy block heels! They feature an open square-shaped toe, a criss-cross strappy design across the foot, thin adjustable ankle and heel straps with a buckle closure, and a block heel. Style with a mini handbag.

    Fit & Features

    • 4" Block heel
    • Open square toe, criss-cross strappy design
    • Adjustable ankle and heel straps with buckle closure
    • Padded insole
    • Coral and yellow heels are faux leather
    • Black heels are faux nubuck
    • Runs true to size

    Style Number/Barcode: 07401-4926

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave Halter Bandeau Bikini Top

    Bring the heat to your summer vacay in this bandeau bikini top featuring a metal rectangular accent and halter tie-back straps. Pair with the matching bikini bottoms.

    Shop Matching Bottoms: Heat Wave V-Cut Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Sweetheart bust
    • Metal rectangular accent
    • Halter tie-back spaghetti straps
    • Lower tie-back straps
    • Runs true to size

    Style Number/Barcode: 07104-000004

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Delight Sleeveless Lace Trim Skater Dress

    When the occasion calls for flair, this sleeveless skater dress delivers with darling delight! Perfect for bridal showers, rehearsal dinners, and graduations. Made from a smooth chiffon fabric, the lace trim straps and hem add a delicate touch. Featuring a square neckline and ruched bust, the flattering skater silhouette will have you twirling all day! Complete the look in block heels.

    Fit & Features

    • Smooth chiffon fabric, stretchy knit lining
    • Square neckline, lace trim straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Lace trim short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3563

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style Icon Strappy Faux Leather Short Block Heels

    These chic strappy short block heels are a must-have for a style icon like you. Designed with smooth faux leather material, they feature a short block heel for comfortable wear, an open square toe, an asymmetric strappy design across the foot, and adjustable ankle and heel straps for a customized fit. Style with classic hoop earrings.

    Fit & Features

    • 2.5" Block heel
    • Faux leather upper, subtle padded insole
    • Open square toe
    • Asymmetric strappy design
    • Adjustable ankle and heel straps with buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4661

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cross My Heart Layered Necklace

    Elevate your style with this layered necklace perfect for accessorizing your outfit. This unique necklace features a layered design with a delicate cross and heart charms. Complete the look in a chic matching set for weekend plans!

    Fit & Features

    • Layered necklace
    • Cross and heart charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-1837

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Arrival Rose Floral Chiffon Maxi Dress

    Make a gorgeous arrival in this rose floral chiffon maxi dress for showers, birthdays, or family parties! The sweetheart neckline and adjustable spaghetti straps provide a flattering and comfortable fit, while the padded bra cups offer support and shape. The maxi-length hem and high front slit add a touch of sultry, making you feel so beautiful! Complete the look in chic wedge sandals and sunnies.

    Fit & Features

    • Rose floral print
    • Chiffon fabric lined with stretchy knit
    • Padded bra cups, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3128

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Vacay Lace-Up Tropical Maxi Dress

    Your summer vacay needs this tropical maxi dress! Made from a stretchy knit fabric adorned with a tropical print, this maxi dress features a flattering cowl neckline, spaghetti straps, and a lace-up back for head-turning allure. The form-hugging fit flaunts your figure while the high side slit offers a show of leg. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Cowl neckline
    • Spaghetti straps, lace up back
    • Form-hugging fit
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5743

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Moment Tie-Front Duster

    You're the moment in this breezy sleeveless tie-front duster, perfect for beach hangs or sunny getaways! 

    Fit & Features

    • Gauze cotton woven fabric
    • Sleeveless 
    • V-neckline
    • Tie-front with beaded ends
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06204-000009

    Category Name: Vacation Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreaming Of Paradise Cowl Neck Tropical Midi Dress

    Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Adjustable spaghetti straps
    • Cowl neckline
    • Bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5613

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Side Up Trendy Sunglasses

    Cool, casual, and just a little bold—these sleek sunnies instantly elevate your look. Perfect for coffee runs, running errands, or whenever you need a stylish shield from the rays.

    Fit & Features

    • Sleek, square-shaped frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000062

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

    Product Badge:
    • Best Seller
  • Howdy Hey Twist Braided Straw Cowboy Hat

    Tip your hat to everyone in this stylish straw cowboy hat at festivals, concerts, or bachelorettes! It's designed with a curved wide brim with a braided twist trim, and adjustable inner strings to get a snug fit. Complete the look with cowboy boots.

    Fit & Features

    • Braided twist trim
    • Wide curved brim
    • Inner adjustable strings
    • Straw material

    Style Number/Barcode: 07302-1642

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hit The City Strapless Slit Crop Top

    Throw on your sunnies and hit the city in this strapless crop top for a flirtatious style! The top boasts a trending strapless sweetheart neckline, a center front adjustable drawstring and slit, and a ruffled trim crop hem. Complete the look in denim jeans and sneakers!

    Fit & Features

    • Brushed knit soft fabric, moderate stretch
    • Strapless sweetheart neckline
    • Center front adjustable drawstring
    • Center slit design
    • Ruffled trim cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5375

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What You Want Strappy Cutout Slit Midi Dress

    This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!

    Fit & Features

    • Double-lined rib knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Strappy cutout twist back
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5663

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Think About Me Lace-Up Floral Skater Dress

    Captivate everyone's thoughts in this floral skater dress sure to be the prettiest pick anyone has ever seen! With a square neckline and spaghetti straps, it's perfect for warmer days. The lace-up back and bow tie adds a playful touch, while the skater silhouette and mini-length hem flatter any figure. Complete the look with an adorable hair bow and sunglasses!

    Fit & Features

    • Floral print, woven fabric lined, no stretch
    • Spaghetti straps
    • Square neckline, bow tie
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5490

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Special Stunner One-Shoulder Cutout Ombre Maxi Dress

    Leave everyone in awe when you're in this ombre maxi dress for sunset cocktails! Featuring a unique one-shoulder neckline with an adjustable spaghetti strap and flirty side cutout, this dress hugs your curves and shows off your legs with a high-side slit along the maxi-length hem and form-hugging silhouette. Complete the look with sparkly bracelets.

    Fit & Features

    • Ombre mesh fabric, stretchy knit lining
    • One-shoulder neckline, adjustable spaghetti strap
    • Side cutout
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5708

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Have It All V-Neck Halter Crop Top

    Care to have it all with this sultry crop top? It boasts a halter V-neckline with a spaghetti strap tie, a low back cut to flaunt some skin, and adjustable side drawstrings let you customize the fit along the cropped hem. Complete the look in women's best-selling bottoms for any casual occasion!

    Fit & Features

    • Knit fabric
    • Halter V-neckline, spaghetti strap tie
    • Low cut back
    • Adjustable side drawstrings
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5353

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Tropical Floral Mesh Maxi Dress

    Activate vacay mode and radiate dreamy vibes in this alluring tropical maxi dress! Designed with an airy sheer mesh fabric with a mini-length knit lining, this maxi-length dress is accented with a blooming tropical floral print for a stunning look. It features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist to accentuate your curves, and a bodycon silhouette with a thigh-high side slit to showcase some leg. Style with stiletto heels for a sunset dinner!

    Fit & Features

    • Tropical floral print
    • Sheer mesh fabric with mini-length knit lining, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Ruched waist, side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5543

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Allure Tie-Front Ruffled Skater Dress

    Captivate with your charming allure in this pretty tie-front ruffled skater dress! Designed with a breezy gauze woven fabric, this short dress is the perfect lightweight style for weekend dates. It features a sleeveless V-neckline with the cutest tie-front bow design, a built-in padded bust, adjustable spaghetti straps so you can find your perfect fit, and a smocked back for added stretch. The high waist flows out to a tiered ruffled skater skirt with an adorable fit-and-flare silhouette. Complete your look with hoop earrings and heeled sandals.

    Fit & Features

    • Gauze woven fabric with woven lining, no stretch
    • V-neckline with tie-front, padded bust
    • Adjustable spaghetti straps
    • High waist, smocked back
    • Tiered ruffled design
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5720

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Party Diva Cropped Rhinestone Halter Top

    A cropped rhinestone halter top that'll inspire your next going-out look! It features a sultry plunge cowl neckline and a partially open back that turns heads. Pair with jeans.

    Fit & Features

    • Sheer mesh fabric with knit lining, moderate stretch
    • Studded rhinestones
    • Plunging halter neckline, cowl bust
    • Mini bar strap at bust
    • Halter neck ties, partially open back 
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5498

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NUDE, BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock