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.
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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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Casually Cool Slit Maxi Dress
Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.
Fit & Features
- Sleeveless scoop neck
- Bungee spaghetti straps
- Form-hugging
- High-cut side slit
- Maxi-length hem
- Rib-knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4883
Category Name: Vacation Dresses & Outfits
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
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Wildflower Energy Cowl Halter Romper
This sheer mesh halter romper mixes floral and animal vibes for a look that’s flirty, fierce, and ready for your next night out!
Fit & Features
- Floral and leopard mix print, mesh-lined fabric
- Halter cowl neckline, spaghetti strap tie
- Open strappy back
- Built-in mini shorts with flirty skirt overlay
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 06503-000082
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: LEOPARD
Available Size: XS, S, M, L
Product Badge:- New Arrival
- Floral and leopard mix print, mesh-lined fabric
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So Darling Woven Drop-Waist Skater Dress
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace.
Fit & Features
- Woven fabric with lace trim woven lining
- Sweetheart neckline, ruched bust, adjustable tie-front
- Tank straps, lace-up back design
- Back zipper and hook-eye closure
- Asymmetric drop-waist, pleated side panels
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3378
Category Name: Vacation Dresses & Outfits
Price: $28.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sun-Kissed Moments Tie-Strap Bikini Bottoms
You'll have sun-kissed moments in these trendy low-rise bikini bottoms featuring tie straps on each side with beaded detailing. Style with the matching bikini top.
Shop Matching Top: Sun-Kissed Moments Triangle Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- Low-rise waist
- Tie straps on each side, beaded details
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000009
Category Name: Vacation Dresses & Outfits
Price: $24.90
Availability: Out of Stock
- Nylon-blend fabric, high stretch
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Desert Sun Lace Ruffle Mini Dress
Sway to the beat of your fave artist in this lace ruffle mini dress boasting a form-hugging fit and shark bite hem that pairs perfectly with boots!
Fit & Features
- Lace lined fabric
- Square neckline, bust tie
- Wide shoulder straps
- Form-hugging fit
- Shark bite ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4006
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: IVORY
Available Size: XXS, S, M, L
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Meet In The Hamptons Linen Wide Leg Pants
These linen wide-leg pants have a Hampton's getaway written all over it! Look cute strolling through the town in these pants featuring a flattering high-rise waist and a hidden back zipper closure. Style with the matching top and a dainty necklace to complete the chic look!
Shop Matching Top: Meet In The Hamptons Linen Crop Top
Fit & Features
- High-rise waist
- Hidden back zipper closure
- Wide-leg silhouette
- Lined linen fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0723
Category Name: Vacation Dresses & Outfits
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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 Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L, XL
Product Badge:- Best Seller
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Sunlight Dream Floral Paisley Silk Scarf
Create a dreamy daytime vibe with this silk scarf featuring a blooming floral paisley print and multiple styling options! Complete the look with a basic bodysuit, jeans, and a coffee in hand to stroll the streets of a cute downtown area.
Fit & Features
- Floral paisley print
- Silky material
- Multiple styling options
Style Number/Barcode: 07305-0450
Category Name: Vacation Dresses & Outfits
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
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Out In The Wild Leopard Crop Top
You could chill… but why would you? This halter top is made for turning heads with a draped cowl neckline and chainlink moment that screams “she knows she’s the vibe.”
Fit & Features
- Leopard print, stretchy mesh knit fabric
- Cowl halter neckline, hoop inserts, spaghetti strap tie
- Open back with spaghetti strap tie
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000198
Category Name: Vacation Dresses & Outfits
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller
- Leopard print, stretchy mesh knit fabric
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Cuddle Time Chenille Crop Cardigan
Wrap yourself in this chenille crop cardigan for a cute and cuddly vibe! The sweater features long sleeves, a ribbed open-front design, and a cropped hem on ultra-soft and cozy chenille knit fabric. Complete the look in the matching cozy pajama top and bottoms for a chill night in!
Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top
Shop Matching Pajama Bottoms: Feeling The Vibe High-Rise Chenille Joggers
Fit & Features
- Long sleeves
- Ribbed open-front design
- Cropped hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0946
Category Name: Vacation Dresses & Outfits
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
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Ruffle Me Up Midi Skirt
Flirty, flowy, and made for vacay vibes! This ruffle-trim midi skirt brings soft drama with a sleek fit and side slit that shows just enough—pair it with the matching top to complete the look.
Shop The Matching Top: Ruffle Me Up Crop Top
Fit & Features
- Smooth double-lined stretchy knit fabric
- High-rise waist
- Side ruched seam and ruffled slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000060
Category Name: Vacation Dresses & Outfits
Price: $28.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Arrived In Style Chiffon Sheer Kimono
Arrive wherever you're headed in this stylish chiffon sheer kimono to elevate your outfit! It features breezy short sleeves, an open front design, side slit accents, and a flowy mid-calf length hem. Layer over a crop top, shorts, and sassy lace-up heels to complete your look!
Fit & Features
- Breezy short sleeves
- Open front design
- Side slit accents
- Flowy mid-calf length hem
- Sheer, airy chiffon fabric
- Runs true to size
Style Number/Barcode: 06204-1333
Category Name: Vacation Dresses & Outfits
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
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Smoke And Mirrors Square Sunglasses
No matter your mood, these square sunglasses are perfect for slipping on when you can't even! They feature a sleek metal frame with cool, smokey pink-tinted lenses and rubber nose supports. Complete the look in a flirty printed sundress for a day out.
Fit & Features
- Square sleek metal frame
- Rubber nose supports
- Smokey pink tinted lenses
Style Number/Barcode: 07008-1006
Category Name: Vacation Dresses & Outfits
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
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Coastal Babe Slip-On Wedge Sandals
For strolls along the coast or any weekend adventure, these slip-on wedge sandals provide comfort and style! They feature a square toe, a wide strap, and a platform sole of faux leather material. Complete the look with cute sunglasses.
Fit & Features
- Square toe, wide strap
- Platform sole
- Wedge style
- Slip-on and off styling
- Faux leather material, cushioned insole
- Runs true to size
Style Number/Barcode: 07404-1093
Category Name: Vacation Dresses & Outfits
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
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Vacay Scandal Tropical Cutout Maxi Dress
Booked the trip? Now bring the drama in this tropical maxi dress! With metal hardware and skin-baring cutouts, this maxi is not for blending in—it's bold, body-hugging, and built for after-hours.
Fit & Features
- Tropical print, mesh fabric, smooth stretchy knit lining
- Halter neckline with hardware accents, spaghetti strap tie
- Bandeau-style cutout bodice with center metal U-ring
- Ruched high waist with hardware accent
- High front slit on a body-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000032
Category Name: Vacation Dresses & Outfits
Price: $45.90
Availability: Out of Stock
Product Badge:- Best Seller
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Sangria Please Striped Halter Top
Can't you imagine wearing this striped halter top while sipping on a sangria? Set the tone this vacay-ready crop top featuring a sleeveless, halter neck, tie-closure, striped pattern, and a smocked back. Complete the look in the matching bottoms.
Shop The Matching Bottoms: Sangria Please Striped Wide Leg Pants
Fit & Features
- Sleeveless, halter neck, tie-closure
- Cropped hem
- Smocked back
- Striped pattern
- Gauze woven fabric, no stretch, fits true to size
Style Number/Barcode: 06003-1568
Category Name: Vacation Dresses & Outfits
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle and Ready Chiffon Halter Maxi Dress
Love to make an entrance? Nail it with this chiffon maxi dress! With cascading ruffles, sultry cutouts, and a leggy slit, this chiffon maxi brings the drama every time.
Fit & Features
- Chiffon fabric, lined with stretchy knit
- Sweetheart halter neckline with tie straps, padded bra cups
- Cutout back and sides
- Cascading ruffle trims
- Flowy silhouette, front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000201
Category Name: Vacation Dresses & Outfits
Price: $59.90
Availability: In Stock
Available Color: IVORY, BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Wandering Bliss Halter Crochet Jumpsuit
Wander in bliss looking so boho in this sleeveless jumpsuit perfect for a music festival or summer vacation! It features a halter V-neckline with tie closure, an open back, a crochet waist, and a flowy wide-leg silhouette on gauze-woven fabric. Complete the look n espadrille wedges.
Fit & Features
- Sleeveless halter V-neckline, tie closure
- Open back
- Crochet waist
- Wide-leg silhouette
- Gauze woven fabric
- No stretch
- Runs true to size
Style Number/Barcode: 06302-0724
Category Name: Vacation Dresses & Outfits
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
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Eyes On You Lace-Up Slit Maxi Dress
Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!
Fit & Features
- Gauze linen-blend woven fabric, stretchy knit lining
- Halter neckline, spaghetti strap ties
- Lace-up back
- Cutout accents
- High front slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000053
Category Name: Vacation Dresses & Outfits
Price: $48.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Sunny Daze Linen Tie-Front Crop Top
Catch the breeze, catch the vibe. This linen tie-front crop top is made for sunny days and carefree moments—easy, airy, and ready for wherever the day takes you.
Shop Matching Bottoms: Sunny Daze Linen Mini Skort
Fit & Features
- Linen woven fabric
- Sleeveless V-neckline
- Tank shoulder straps
- Tie-front design
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000023
Category Name: Vacation Dresses & Outfits
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sunny Daze Linen Mini Skort
Catch the breeze, catch the vibe. This linen mini skort is made for sunny days and carefree moments—easy, airy, and ready for wherever the day takes you.
Shop Matching Top: Sunny Daze Linen Tie-Front Crop Top
Fit & Features
- Linen woven fabric
- Mid-rise waist
- Mini-length overlay, A-line silhouette
- Hidden shorts
- Runs true to size
Style Number/Barcode: 06303-000034
Category Name: Vacation Dresses & Outfits
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Cozy Bliss Faux Fur Bucket Hat
Fit & Features
- Oversized bucket design
- Faux fur fabrication
Style Number/Barcode: 07302-1734
Category Name: Vacation Dresses & Outfits
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
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Eyes on You Abstract Print Cutout Mini Dress
You didn’t just enter the room—you owned it. With a bold cutout and curve-hugging fit, this iconic abstract print mini dress is your go-to for nights out where the vibe is flirty and fearless.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless sweetheart neckline, padded bra cups
- Bust cutout with lattice design, large waist cutout
- Adjustable spaghetti straps
- Ruching, mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000288
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Party Hour Rhinestone Beer And Lime Earrings
Dive into fun with these rhinestone beer and lime earrings. Featuring a lime slice post and sparkling beer bottle design, these earrings are your perfect party pals. Cheers to style!
Fit & Features
- Lime slice post
- Hanging beer bottle design
- Mini rhinestone embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2321
Category Name: Vacation Dresses & Outfits
Price: $9.90
Availability: Out of Stock