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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Real Style Faux Leather Platform Heels
These faux leather heels have got real style! They feature a square toe, wide toe strap, a thin block heel, a platform, an ankle strap with buckle closure, and a slightly cushioned insole. Complete the look with a trendy crossbody bag for a daytime soiree!
Fit & Features
- Square toe, wide toe strap
- Thin block heel, platform
- Ankle strap with buckle closure
- Slightly cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4406
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Away This Weekend Buckle Platform Wedges
These platform wedges are ready for your weekend away! They feature a square toe, a faux leather strap with studs and a buckle detail, a wooden-like sole, and a wrap-style ankle strap with a buckle closure and stud accents. Complete the look in a wide-leg jumpsuit for a dinner with a view!
Fit & Features
- Square toe
- Faux leather strap, studs, buckle detail
- Wooden-like platform sole
- Wrap-style ankle strap, buckle closure
- Runs true to size
Style Number/Barcode: 07406-0335
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Looks Mesh V-Neck Babydoll Dress
Showcase a dreamy look in this mesh babydoll dress perfect for date nights or parties! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched bust seams, and a flattering babydoll style silhouette with a mini-length hem. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Ruched bust seams
- Babydoll style silhouette
- Mini-length hem
- Airy mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4971
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paint Me In Floral V-Neck Maxi Dress
This floral maxi dress will fit like a dream and give off major artsy vibes! It features a sleeveless V-neckline, spaghetti straps, a hip-hugging fit, and a sultry front slit along the flowy hem. Complete the look in dainty earrings for a daytime soiree!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Hip-hugging fit
- Front slit, flowy maxi-length hem
- Floral watercolor print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5018
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay In Bali One-Shoulder Maxi Dress
Vacation in sultry style wearing this maxi dress! Serve major looks on the island in this dress featuring a sleeveless one-shoulder neckline, a tank strap with a hoop insert, and a form-hugging slim silhouette with a high side slit and ruched seam on textured knit fabric. Complete the look in chic sandals.
Fit & Features
- Sleeveless one-shoulder neckline
- Tank strap, hoop insert
- Form-hugging, slim silhouette
- High side slit, side ruched seam
- Maxi-length hem
- Textured knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4970
Category Name: Vacation Looks
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take Me Away Tube Midi Dress
Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!
Fit & Features
- Texture knit cotton-blend fabric, moderate stretch
- Sweetheart strapless tube neckline
- Twist bust
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000018
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Modern Marvel One-Shoulder Mini Dress
Strut looking like a modern work of art in this marble-printed mini dress all over town! It features a sleeveless one-shoulder neck, an adjustable spaghetti strap, a side adjustable ruched string, and a bodycon silhouette. Complete the look with hoop earrings.
Fit & Features
- Sleeveless one-shoulder neck
- Adjustable spaghetti straps
- Side ruched string
- Bodycon silhouette
- Mini-length hem
- Marble-printed mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4989
Category Name: Vacation Looks
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What A Sight Eyelet Lace Lace-Up Dress
You'll be quite a dreamy sight in this eyelet lace skater dress! Perfect for wedding showers, grabbing lunch with the girls, or backyard parties. It features adorable puff short sleeves, a sweetheart neck with an underbust seam, an open lace-up back, and a flattering short-length silhouette. Complete the look in strappy block heels.
Fit & Features
- Puff short sleeves
- Sweetheart neck, underbust seam
- Open lace-up back
- Skater silhouette
- Short-length hem
- Eyelet lace cotton fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4946
Category Name: Vacation Looks
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Intentions Floral Tube Top
Show off your sweet side in this adorable tube top! It features a sweetheart neckline with a ruched bust, halter spaghetti straps, a smocked back panel, and a majorly cropped hem. The woven fabric features an all-over ditsy floral print pattern. Style with the matching skater skirt for a brunch-ready look.
Shop Matching Bottoms: Sweet Intentions Floral Skater Skirt
Fit & Features
- Sleeveless sweetheart neckline, ruched bust
- Halter spaghetti straps, tie at the back of the neck
- Smocked back panel
- Cropped fit
- Ditsy floral print
- Woven fabric, front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1833
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Intentions Floral Skater Skirt
Show off your sweet side in this adorable skater skirt! It features a high-rise smocked waist with an adjustable drawstring, pleated detailing, and a short, fit and flare silhouette. The woven fabric features an all-over ditsy floral print pattern. Style with the matching tube top for a brunch-ready look.
Shop Matching Top: Sweet Intentions Floral Tube Top
Fit & Features
- High-rise smocked waist, elastic waistband
- Adjustable drawstring
- Pleated detailing
- Short hem, fit and flare silhouette
- Ditsy floral print
- Woven fabric, full knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06301-0133
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Guru Pleated Bandeau Top
Elevate your island vacation look with this sassy bandeau crop top perfect for dinner and drinks! It features a sleeveless halter neckline with tie closure and is composed of a pleated satin fabric with lining. Style with the matching bottoms.
Shop Matching Bottoms: Island Guru Pleated Wide Leg Pants
Fit & Features
- Sleeveless halter neckline, tie closure
- Cropped hem
- Pleated satin fabric with lining
- No stretch
- Runs true to size
Style Number/Barcode: 06003-2135
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Guru Pleated Wide Leg Pants
Elevate your island vacation look with these sassy satin pants perfect for dinner and drinks! It features a flattering high-rise elasticized smocked waist, and a wide-leg silhouette and is composed of pleated satin fabric with lining. Style with the matching top.
Shop Matching Top: Island Guru Pleated Bandeau Top
Fit & Features
- High-rise elasticized smocked waist
- Wide-leg silhouette
- Pleated satin fabric with lining
- No stretch
- Runs true to size
Style Number/Barcode: 06402-0621
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Running Wild Zebra Print Mini Skirt
Look stylish in this zebra print mini skirt running wild keeping up with your social calendar! It features a high-rise elasticized waist, a bodycon silhouette, and a flirty slit hem on brushed knit stretchy fabric. Complete the look with the matching top.
Shop The Matching Top: Running Wild Zebra Print Crop Top
Fit & Features
- High-rise elasticized waist
- Bodycon silhouette
- Slit mini-length hem
- Zebra print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06501-0787
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Running Wild Zebra Print Crop Top
Look stylish in this zebra print mini skirt running wild keeping up with your social calendar! It features a sleeveless halter neckline, spaghetti straps, an open lace-up back, and a fitted crop hem on brushed knit stretchy fabric. Complete the look with matching bottoms.
Shop The Matching Bottoms: Running Wild Zebra Print Mini Skirt
Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, lace-up open back
- Fitted crop hem
- Zebra print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06001-4696
Category Name: Vacation Looks
Price: $3.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picnic Date Ditsy Floral Chiffon Romper
This adorable ditsy floral chiffon romper will have you picture-perfect for a picnic date! It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist with a sheer floral crochet trim, flowy shorts, and a fit and flare silhouette. The airy chiffon fabric features a dainty ditsy floral print pattern. Complete the look with espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, back zipper closure
- High waist, sheer floral crochet trim
- Flowy shorts, fit and flare silhouette
- Ditsy floral print
- Sheer chiffon fabric, lining
- Runs true to size
Style Number/Barcode: 06403-0252
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Daze Button Crop Vest
The perfect denim vest to give our outfit a cute western vibe! It features a sleeveless V-neck, button-down front, faux pockets, and a curved crop hem. Style with best-selling bottoms for a festival or an art walk downtown!
Fit & Features
- Sleeveless V-neck
- Button-down front
- Faux pockets
- Curved, crop hem
- Non-stretch rifid denim fabric
- Runs true to size
Style Number/Barcode: 06203-0491
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feel The Rhythm Crochet Lace-Up Vest
Feel the rhythm in this crochet vest perfect for festivals or concerts! It features a sleeveless V-neckline, wide shoulder straps, a front lace-up design, and a pointed crop hem. Complete the look in trendy denim shorts.
Fit & Features
- Sleeveless V-neckline
- Wide shoulder straps
- Front lace-up design
- Pointed crop hem
- Crochet fabric, sewn-in knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4803
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Meet In The Hamptons Linen Crop Top
This linen crop top has a Hampton's getaway written all over it! Look cute strolling through the town in this top featuring a sleeveless halter V-neckline and dual tie-back neck and lower back straps. Style with the matching bottoms and a dainty necklace to complete the chic look!
Shop Matching Bottoms: Meet In The Hamptons Linen Wide Leg Pants
Fit & Features
- Sleeveless halter V-neckline
- Dual tie-back neck and lower back straps
- Cropped hem
- Lined linen fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2163
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All The Attention Abstract Split Crop Top
Command attention in this striking halter crop top featuring a flattering twisted neckline, a daring split design, and a cropped length that perfectly highlights your figure.
Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining
- Halter plunge twist neckline, tie closure
- Center split design
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000167
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Artsy Blooms Floral Mini Skirt
Create an artsy-chic look with this floral mini skirt for an evening downtown! It features a high-rise waist, a front ruched seam atop a slit hem, and a bodycon silhouette on stretchy mesh-lined fabric. Style with a crop top and heels.
Fit & Features
- High-rise waist
- Front ruched seam
- Bodycon silhouette
- Mini-length hem with slit
- Floral artsy bloom print
- Mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0802
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Look Your Cutest Floral Chiffon Mini Skirt
Look your cutest in this floral mini skirt for a stylish stroll downtown to brunch! It features a high-rise waist, a form-hugging fit, and an asymmetrical ruffle trim on airy chiffon fabric. Complete the look in a basic strapless top and heels.
Fit & Features
- High-rise waist
- Hidden side zipper and hook-eye closure
- Form-hugging fit
- Asymmetrical ruffle trim, mini-length hem
- Ditsy floral print
- Airy chiffon woven fabric
- Runs true to size
Style Number/Barcode: 06401-0490
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Miami Nights Ruched Mini Skirt
Bring the heat and take on the night scene in this alluring mini skirt! It features a high-rise elasticized waist, ruched detailing down the side and back seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric offers plenty of stretch. Style with the matching crop top and a pair of strappy stilettos.
Shop Matching Top: Miami Nights One-Shoulder Crop Top
Fit & Features
- High-rise elasticized waist
- Ruched side and back seams
- Mini-length hem
- Form-hugging fit
- Sheer mesh fabric, full knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0783
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miami Nights One-Shoulder Crop Top
Bring the heat and take on the night scene in this alluring crop top! It features a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap, ruched detailing, and a fitted cropped hem. The lined mesh fabric offers plenty of stretch. Style with the matching mini skirt and a pair of strappy stilettos.
Shop Matching Bottoms: Miami Nights Ruched Mini Skirt
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Single adjustable spaghetti strap
- Ruching
- Fitted cropped hem
- Sheer mesh fabric, full knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4672
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Find Lace-Up Cork Block Heels
Embrace the warmer months with these cork block heels that are the cutest find! They feature an open almond-shaped toe, a thin strappy design across the foot, a heel strap, a thin lace-up strappy design that wraps around the leg, and a cork block heel. Style with a mini handbag.
Fit & Features
- Open almond-shaped toe
- Thin strappy design across the foot
- Heel strap
- Thin strappy lace-up wrap-around design, tie closure
- Cork block heel
- Faux leather insole and straps
- Runs true to size
Style Number/Barcode: 07401-4315
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale