Vacation Dresses & Outfits
Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.
HomeVacation Dresses & Outfits

Vacation Dresses & Outfits
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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.
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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 Dresses & Outfits
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- 4" Block heel
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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 Dresses & Outfits
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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 Dresses & Outfits
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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 Dresses & Outfits
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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 Dresses & Outfits
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Dresses & Outfits
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Favorite Fleur V-Neck Floral Chiffon Skater Dress
Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.
Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- V-Neckline, tie front
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3135
Category Name: Vacation Dresses & Outfits
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold New Look Corset Lace-Up Linen Skater Dress
Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.
Fit & Features
- Linen blend fabric lined with stretchy knit
- Sweetheart neckline with bust tie
- Adjustable straps, side zipper and hook-eye closure
- Strappy lace-up back
- Flexible boning
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3791
Category Name: Vacation Dresses & Outfits
Price: $49.90
Availability: In Stock
Available Color: BLACK, LIGHT, BLUE, WHITE
Available Size: XS, S, M, L, XL
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Sunny Energy Halter Cut Out Wide Leg Jumpsuit
Bring the sunny energy in this halter cut-out wide leg jumpsuit wherever you go! This sultry texture knit jumpsuit features a halter spaghetti strap with tie closure for a perfect fit, along with a cutout bust design to show some skin, and a flattering wide-leg silhouette for an easy, breezy style. Complete the look with sunnies and sandals!
Fit & Features
- Texture knit stretchy fabric
- Halter spaghetti strap
- Cut out bust
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2472
Category Name: Vacation Dresses & Outfits
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Appearance Side-Tie Wrap Denim Skort
Your summer style wouldn't be the same without this mini denim skort to make stylish appearances! This form-hugging, high-waisted denim skort boasts a stylish faux wrap skirt overlay with a side tie, adding both function and flair to your wardrobe. The frayed hem adds a touch of edginess. Complete the look in a basic top.
Fit & Features
- Dark wash denim, slight stretch
- High-rise waist, front zipper closure
- Faux wrap skirt overlay, side-tie
- Form-hugging fit
- Frayed short hem
- Runs true to size
Style Number/Barcode: 06603-0390
Category Name: Vacation Dresses & Outfits
Price: $36.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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Breezy Chic Floral Embroidered Chiffon Skater Dress
This breezy chic floral chiffon skater dress is perfect for your summer parties! The airy sheer embroidered chiffon fabric is detailed with a dainty floral print and includes a stretchy full-length knit lining. The short dress features a sleeveless sweetheart neckline, a bustier-style bodice with a padded bust and structured underwire, and ruched cups. The adjustable spaghetti straps lead to a partially smocked back design for added stretch with a secure back zipper closure. The front faux buttons lead to a high waist seam flowing out to a short skater skirt with a flirty fit and flare A-line silhouette. Complete your look with strappy sandals.
Fit & Features
- Sheer embroidered chiffon fabric, floral print, stretchy knit lining
- Sweetheart neckline, bustier bodice, padded bust with underwire, ruching
- Adjustable spaghetti straps
- Partial stretchy smocked back, zipper with hook and eye closure
- Front faux buttons, high waist seam
- Fit and flare A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3009
Category Name: Vacation Dresses & Outfits
Price: $49.90
Availability: Out of Stock
Product Badge:- Sale
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Radiant Accent Floral Boho Satin Scarf
The perfect satin scarf to give your outfit a radiant accent! The silky satin woven material is designed with a vibrant floral bohemian-inspired print for a trendy allure. Style this scarf as a pretty headwrap, around your neck, or tied on your bag as a chic accent! Complete the look with a sleek choker necklace.
Fit & Features
- Silky satin woven material
- Floral bohemian print
- Multiple ways to style and wear
Style Number/Barcode: 07305-0495
Category Name: Vacation Dresses & Outfits
Price: $12.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
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Romance That Wows Large Blossom Floral Maxi Dress
Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!
Fit & Features
- Large blossoming floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3343
Category Name: Vacation Dresses & Outfits
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Be My Forever Ribbon Bow Bodycon Mini Dress
Flattery will get you everywhere in this sleeveless mini dress perfect for boasting an adorable look! The scoop neckline is adorned with delicate lace and charming bow detail, while the tank shoulder straps give a flirty touch. The bodycon silhouette and mini-length hem finish this flawless dress. Complete the look in platform high heels for a party.
Fit & Features
- Woven fabric with minimal stretch
- Scoop neckline, lace and ribbon trim, bow
- Back zipper and hook-eye closure
- Tank shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5817
Category Name: Vacation Dresses & Outfits
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale