Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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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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Free Spirited Paisley Tie-Back Crop Top
Calling all free-spirited babes! This crop top is perfect for festivals and your warm-weather closet. It features adorable puff short sleeves, a scoop neck, and a flirty tie-back on woven fabric with a boho paisley-floral print. Complete the look in trendy denim shorts.
Fit & Features
- Puff short sleeves
- Scoop neck
- Cropped hem
- Tie-back design
- Paisley-floral print
- Non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 06003-1924
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty And Bold Floral Jelly Sandals
Pretty and bold, these floral jelly sandals add a casual-chic vibe. They feature a square-shaped toe, a wide toe strap with a floral pom design, an open back for easy on-and-off styling, and a flat sole for comfortable wear. Style with a mini handbag.
Fit & Features
- Square-shaped toe
- Wide toe strap
- Floral pom design, faux leather material
- Open back
- Flat sole
- PVC material
- Runs true to size
Style Number/Barcode: 07404-1126
Category Name: Vacation Looks
Price: $8.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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In Spring Floral Block Heel Mules
Get in the spring of things in these fresh and flirty floral mules to elevate every outfit this season! They feature a square toe, dual straps with floral accents, and a block heel, and are composed of faux leather material. Complete the look in a cute short dress for a graduation ceremony or birthday!
Fit & Features
- Square toe
- Dual straps with floral accents
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4134
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Level Up Your Look Cargo Mini Skirt
Level up your cute and casual everyday look with this of-the-moment cargo mini skirt. It features a high-rise waist with belt loops, a front button closure, back pocket flaps, cargo-style side pockets with adjustable straps and buckles, a mini-length hem, and a form-hugging fit. Style with a corset top and clear mules.
Fit & Features
- High-rise waist, belt loops
- Front snap-button closures, hidden zipper closure
- Back faux flap pockets
- Cargo-style side pockets, adjustable straps, buckles
- Mini-length hem, form-hugging fit
- Twill denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0153
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cute In Chevron Print Mesh Flare Pants
You'll look cute in these chevron print pants for festival season or hitting up the country bar! It features a high-rise elasticized waist, a hip-hugging fit, and a flared hem. The semi-sheer mesh fabric features a built-in knit panty lining. Complete the look with the matching top.
Shop Matching Top: Cute In Chevron Print Mesh Crop Top
Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flared hem
- Chevron print
- Mesh fabric, knit panty lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-2248
Category Name: Vacation Looks
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Slay Tropical Print Midi Dress
Slay your vacay look with this curve-hugging tropical print midi dress! It features a sleeveless V-neckline, spaghetti straps, a ruched side seam, a midi-length asymmetric hem creating a chic side slit, and a bodycon silhouette. The all-over tropical palm leaf print will really bring those vacay vibes. Complete the look with clear mules.
Fit & Features
- Sleeveless V-neckline, spaghetti straps, bust lining
- Ruched side seam
- Midi-length asymmetric hem, side slit
- Bodycon silhouette
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4948
Category Name: Vacation Looks
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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 Looks
Price: $7.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dream Escape Tropical Midi Dress
Pack right for your dream escape with this tropical print midi dress perfect for a dinner with a beachside view! It features a sleeveless V-neckline, adjustable spaghetti straps that crisscross in the back, a bodycon fit, and a ruched side seam to accentuate your curves atop a sultry slit. The smooth knit fabric features a gorgeous tropical floral print that will give off major vacay vibes. Complete the look with sleek earrings and a choker necklace.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, crisscross back
- Bodycon silhouette
- Side ruched seam, slit accent
- Asymmetric midi-length hem
- Tropical floral print, knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4957
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Style In Check Utility Denim Romper
Keep your style in check and looking fresh in this denim utility romper perfect for weekend road trips or exploring downtown! It features short sleeves, a collar neckline, front zipper closure, flap pockets, a belted waist with buckle closure, a short-length hem, and a form-hugging fit. Complete the look in trendy sandals.
Fit & Features
- Short sleeves, collar neckline
- Front zipper closure
- Belted waist, buckle closure, belt loop accents
- Chest flap pockets
- Short-length hem
- Medium-wash denim fabric, moderate stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0322
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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That 70s Chick Retro Print Crop Top
Inspired by the groovy era, you'll look like a cute chick in this retro crop top perfect for parties! It features a sleeveless bodice, convertible shoulder straps that can be worn in multiple ways, a fitted, cropped hem, and a geometric-retro print design. Complete the look with high-rise denim and platform heels.
Fit & Features
- Sleeveless bodice
- Convertible shoulder straps, multiple ways to wear
- Fitted, cropped hem
- Geometric-retro print design
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4740
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Mode Basic Strap Sandals
Get into a chill weekend mode with these basic strap sandals. They feature an almond-shaped toe, a wide banded toe strap, adjustable ankle and heel straps, and a flat sole for comfortable wear. Style with a crop top and denim shorts.
Fit & Features
- Almond-shaped toe
- Wide banded toe strap
- Adjustable ankle and heel straps
- Buckle detail
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1076
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Paradise Tropical Print Midi Dress
You'll be ready for your paradise getaway with this tropical print midi dress! It features a sleeveless V-neck, spaghetti straps, a sultry cutout back, a bodycon silhouette, and an asymmetrical side slit cutout. Complete the look in wedges.
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Cutout back
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Tropical print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4987
Category Name: Vacation Looks
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Festival Fun Crochet Tie-Back Crop Top
Make your mark at festivals this season in this crochet knit crop top featuring bell long sleeves, a plunge V-neck, and a sassy open back with tie closure. Style with high-rise denim shorts for a trendy look!
Fit & Features
- Bell long sleeves
- Plunge V-neck
- Cropped hem
- Open back with tie closure
- Crochet knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06001-4627
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Worth It Linen Wide-Leg Pants
These linen pants are worth taking on your next weekend adventure! They feature a high-rise waist, back zipper closure, side pockets, and a wide-leg silhouette. Complete the look with the matching top.
Shop Matching Top: Worth It Linen Tube Top
Fit & Features
- High-rise waist
- Back zipper closure
- Side pockets
- Wide-leg silhouette
- Linen fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06302-0726
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Worth It Linen Tube Top
This linen-blend tube top is worth taking on your next weekend adventure! It features a sleeveless bodice, a convertible design so you can style it multiple ways, and a cropped hem. Complete the look with the matching bottoms.
Shop Matching Bottoms: Worth It Linen Wide-Leg Pants
Fit & Features
- Sleeveless bodice
- Convertible design
- Multiple ways to style
- Cropped hem
- Linen-blend fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06003-2167
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Sleeveless bodice
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Remy High-Rise Destructed Frayed Shorts by Windsor Denim
Take your everyday 'fit up a notch with the Remy destructed frayed shorts by Windsor Denim. They feature a high-rise waist, on-trend destructed detailing, and a majorly frayed cut-off hem. The light-wash denim fabric has a rigid fit with no stretch. Style with a graphic tee and sneakers.
Fit & Features
- High-rise waist
- Destructed accents
- Frayed cut-off hem
- Front button-down closure
- Five-pocket and belt loop design
- Light wash denim fabric, rigid fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0247
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Retro Upgrade Sleek Rectangle Sunglasses
Upgrade your look with these retro-cool sunglasses featuring sleek rectangular tinted lenses and clear plastic arms. Style with a casual mini dress for a pool party!
Fit & Features
- Sleek rectangular tinted lenses
- Clear plastic arms
- 100% UV protection
Style Number/Barcode: 07008-0999
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Outer Limits Silver Racer Sunglasses
Your style will look out of this world in these retro-fab silver sunglasses featuring a geometric style plastic frame, tinted lenses, and a sleek design. Complete the look in lug booties.
Fit & Features
- Silver geometric style plastic frame
- Sleek design
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0997
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Attitude Round Metal Frame Sunglasses
Serve major attitude in these on-trend round sunglasses featuring a sleek metal frame, brown tinted lenses, rubber nose, and arm supports. Complete the look in sassy sandals for a day out with friends!
Fit & Features
- Sleek metal round frame
- Brown tinted lenses
- Rubber nose and arm supports
- 100% UV protection
Style Number/Barcode: 07008-1001
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Strides Chain-Detail Jelly Sandals
Make trendy strides in these of-the-moment jelly sandals. They feature a square toe, a dual strap design with chunky chain-link accents, an open back for easy on-and-off styling, and a flat sole. Style with a casual dress and a mini handbag.
Fit & Features
- Square-shaped toe
- Dual strap design
- Chunky chain-link accents
- Open back
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-1130
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stand Out Mid-Rise Denim Hot Shorts
Designed to stand out, these mid-rise denim hot shorts are everything for the next concert or festival!
Fit & Features
- Denim fabric with color wash tint effect
- Mid-rise waist
- Hidden front hook-eye and zipper closure
- Seam detailing
- Fitted cheeky fit
- Runs true to size
Style Number/Barcode: 06603-0445
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Can't Help It Jelly Bejeweled Flat Sandals
You can't help but flaunt your glam in these clear jelly sandals featuring a square toe, a wide strap with statement rhinestone jewels, and a flat sole. Style with a chic handbag for a daytime soiree!
Fit & Features
- Square toe
- Wide strap
- Rhinestone jewels
- Flat sole
- Clear jelly material
- Runs true to size
Style Number/Barcode: 07404-1128
Category Name: Vacation Looks
Price: $5.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Little Princess Jeweled Thong Sandals
Grace everyone with your princess energy in these stunning thong sandals to bring the glamour to sitting poolside in a private cabana with the girls! They feature a square toe, colored gemstones with rhinestone trim on thin PVC clear straps, a flat sole, a metallic footbed, and a colored rhinestone ankle chain strap with a lobster clasp closure. Complete the look in a chic duster kimono to layer over your swimsuit!
Fit & Features
- Square toe
- Colored gemstones, rhinestone trim
- PVC clear thong straps
- Flat sole, metallic footbed
- Colored rhinestone ankle chain strap
- Lobster clasp closure
- Runs true to size
Style Number/Barcode: 07404-1138
Category Name: Vacation Looks
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy In Floral Satin Midi Dress
Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Curve-hugging, slim silhouette
- Side slit accent
- Midi-length hem
- Floral print, silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4985
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale