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 Looks
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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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Express Your Style V-Neck Ruffle Bodycon Mini Dress
Express your devotion to style in this charming sleeveless mini dress perfect for casual showers or brunch! This dress features adjustable spaghetti straps for the perfect fit, a flirty V-neckline with a bust tie for added charm, and a bodycon fit to accentuate your curves. The mini-length hem and ruffle trim throughout add a touch of romance to this head-turning dress. Complete the look with earrings.
Fit & Features
- Ruffle trim throughout, knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline with bust tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5789
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Serenity V-Neck Crochet Crop Top
Flirty yet casual, this crochet crop top is perfect for grabbing cocktails at sunset by the beach! The delicate v-neckline and shoulder straps give a flattering silhouette, while the cropped hem adds a cute touch. Complete the look in a flowy maxi skirt and sandals.
Fit & Features
- Sheer crochet fabric, no stretch
- V-neckline
- Shoulder straps
- Cropped length
- Runs true to size
Style Number/Barcode: 06005-2015
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetie Status Halter Crochet Trim Babydoll Dress
You'll look absolutely adorable in this babydoll dress at showers, birthdays, or backyard parties! The halter neckline and cutout bodice add a touch of allure, while the crochet trim and babydoll silhouette create a delicate and feminine look along the short-length hem. Complete the look in sandals and hoop earrings.
Fit & Features
- Gauze woven fabric, woven lining, no stretch
- Halter neckline with spaghetti strap ties
- Cutout bodice
- Crochet trim
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-5421
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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About A Girl Bow Canvas Tote Bag
Carry your essentials in style with this charming bow canvas tote bag. Perfect for shopping trips, beach days, or casual outings, this adorable tote adds a cute touch to any outfit.
Fit & Features
- Bow print design
- Top handles
- Spacious interior
- Canvas material
Style Number/Barcode: 07203-000032
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Profound Bloom Off-The-Shoulder Floral Skater Dress
You'll be blossoming from all the compliments you'll get wearing this off-the-shoulder floral dress! This skater dress features a playful sweetheart neckline, a bust tie, and a ruffled short-length hem bringing plenty of sass and sweetness to your style. Complete the look with earrings and strappy sandals for any occasion!
Fit & Features
- Floral print, woven fabric, bust lining
- Off-the-shoulder, sweetheart neckline
- Padded bra cups, back zipper and hook-eye closure
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3459
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Escape Tropical Print Palazzo Pants
Escape to your dream vacay in these tropical print palazzo pants offering a high-rise waist and a flowy, wide-leg silhouette. Style with the matching tie-front top and your fave sandals.
Shop Matching Top: Sunny Escape Tropical Print Tie-Front Top
Fit & Features
- Woven fabric
- Tropical print
- High-rise waist, front button and hidden zipper closure
- Pleating
- Wide-leg fit
- Relaxed silhouette
- Runs true to size
Style Number/Barcode: 06302-000002
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Icon Basic Thong Sandals
A picture-perfect sunny day calls for these basic thong sandals to style with your everyday look!
Fit & Features
- Almond toe
- Sleek thong toe strap
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-000003
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Graceful Presence Sweetheart Floral Skater Dress
Have a graceful presence in this floral skater dress at showers or graduations! A charming dress with a sweetheart neckline and tie spaghetti straps, the skater silhouette flatters your figure, while the short-length hem adds a playful touch. Complete the look in wedge sandals.
Fit & Features
- Floral print, woven fabric lined with stretchy knit
- Tie spaghetti straps
- Sweetheart neckline
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3194
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Getaway Puff Short Sleeve Floral Romper
This floral romper is the perfect piece to pack for your next sunny getaway or weekend plans! With delicate puff sleeves, a flattering square neckline and bust tie, and a comfortable stretchy smocked back, this short-length romper will have you looking and feeling stunning on your next adventure. Complete the look with hoop earrings.
Fit & Features
- Floral print, woven fabric, stretchy knit lining
- Puff short sleeves
- Square neckline with bust tie
- Stretchy smocked back
- Short-length
- Runs true to size
Style Number/Barcode: 06303-0257
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Beauty Sheer Crochet Coverup Top
Layer on this breezy sheer crochet coverup top for an effortless pretty vibe! Made with a trendy open-knit crochet fabric, it features a wide boat neckline, long dolman-style sleeves, a long-length hem with high side slits for added movement, and an overall relaxed flowy fit. Pair with a basic bralette with denim shorts for the perf summer look.
Fit & Features
- Sheer open-knit crochet fabric, minimal stretch
- Boat neckline
- Long dolman sleeves
- Long-length hem, side slits
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-1963
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picking Flowers Halter Strappy Back Daisy Skater Dress
This daisy print skater dress will have you dreaming of sunny days picking flowers! The halter spaghetti strap neckline perfectly frames your shoulders while the cutout bodice adds a touch of allure. The strappy open back creates a stunning statement and the skater silhouette and tiered ruffled short-length hem give you a playful and fun look. Complete the look in sandals for a brunch or day date!
Fit & Features
- Daisy print, woven fabric with lining, no stretch
- Spaghetti strap
- Strappy open back
- Ruffles
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5794
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Set Up High Rise Geometric Palazzo Pants
Super cute and perfect for getaways or weekend plans, these palazzo pants are stylish and comfortable for anything on your calendar! They feature a flattering smocked high-rise waist, a wide-leg silhouette, and a trendy geometric print on woven fabric. Complete the look with the matching top.
Shop The Matching Top: All Set Up Geometric Bandeau Halter Crop Top
Fit & Features
- Geometric print, woven fabric, no stretch
- Smocked high-rise waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1420
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jet-Set to Paradise Strappy Cutout Tropical Knit Jumpsuit
This alluring tropical knit jumpsuit will have you ready to jet-set to paradise! The stretchy knit fabric showcases a contrasting tropical palm leaf print for a dreamy vacay vibe. The jumpsuit is shaped with a sleeveless strappy halter neckline with a cross-front cutout design and a sultry waist cutout. The halter straps lead to an open strappy lattice back design with a tie closure to find your perfect fit. Front ruching at the waist offers a flattering look, leading to a relaxed wide-leg silhouette. Complete your look with espadrille sandals.
Fit & Features
- Tropical printed stretchy knit fabric
- Sleeveless strappy halter neckline
- Cross-front cutout design, waist cutout
- Open strappy lattice back design, tie closure
- Ruched waist
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-2456
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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New You Sweetheart Halter Crop Top
The new you and look has arrived with this sassy halter crop top perfect for beach days and casual hangs! The sleeveless rib knit top fits and flatters with a sweetheart neckline, halter spaghetti strap tie, cinched bust detail, and cropped hem. Complete the look in denim shorts and shades!
Fit & Features
- Stretchy rib knit fabric
- Sweetheart neckline
- Spaghetti strap tie
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1935
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Cutie Bell Sleeve Crochet Crop Top
Show off the cutest boho vibe in this breezy crochet crop top! Designed with an airy sheer crochet knit fabric, this top is perfect for summer days spent by the coast. It features a wide scoop neckline, long bell sleeves with a stylish flare, a tie-back design at the neck, and a cropped hem with a form-hugging fit. Complete your look with the matching wide-leg pants and a pair of strappy sandals!
Shop Matching Bottoms: Boho Cutie Crochet Wide-Leg Pants
Fit & Features
- Sheer crochet knit fabric, minimal stretch
- Scoop neckline
- Long bell sleeves
- Tie-back design
- Fitted cropped hem
- Bra lining not included
- Runs true to size
Style Number/Barcode: 06005-1951
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Sheer crochet knit fabric, minimal stretch
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Perfectly Comforting Tie Front Longline Duster
A longline duster features trendy flared long sleeves and dual tie-front design and is made from a soft and stretchy rib knit fabric making it perfect for layering.
Fit & Features
- Rib knit soft and stretchy material
- Flared long sleeves
- Dual tie-front design
- Longline hem
- Runs true to size
Style Number/Barcode: 06202-0488
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fluttering Elegance Rhinestone Butterfly Earrings
Create a statement in these elegantly whimsical earrings! Featuring a top rhinestone post with cascading dainty chain links with rhinestone embellished butterfly charms. Complete the look with a ring set for any occasion!
Fit & Features
- Top rhinestone post
- Cascading dainty two-row chain-link design
- Rhinestone embellished butterfly charms
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2056
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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 Looks
Price: $11.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In The Spotlight Strapless Ruched Corset Top
You'll be the center of attention in this corset top everywhere you go! Made from a ruched woven fabric, this corset top sets the bar high with a strapless neckline, flexible boning, and a cropped hem to flaunt your figure. Plus, the hidden back hook and eye fasteners secure the style. Complete the look in cute jeans for any plans!
Fit & Features
- Ruched woven fabric
- Strapless neckline
- Hidden back hook and eye fasteners
- Flexible boning
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2296
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Mode V-Cut Bikini Bottoms
Activate sunny mode with these hot bikini bottoms featuring a V-cut design, scrunched detailing at the back, and a cheeky fit. Style with the matching bikini top to be sitting pretty poolside!
Shop Matching Top: Sunny Mode Ruched Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- V-cut waist
- Scrunched back
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000008
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Nylon-blend fabric, high stretch
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Ultimate Chic Choice Floral Tie-Back Short Dress
For the ultimate chic choice, pick this floral short dress for all your summer plans! The sweetheart neckline and spaghetti straps give a flirty touch, while the dual tie-back design ensures a perfect fit. The underwire bust and flexible boning offer support and structure, with a short-length hem for a stunning silhouette. Complete the look with dainty chic earrings.
Fit & Features
- Ditsy floral print, woven fabric lined with stretchy knit
- Sweetheart neckline, underwire bust
- Spaghetti straps
- Dual tie-back design
- Flexible boning
- Short-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3447
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ocean Dreams Seashell Mesh Bikini Top
Get beach-ready in this mesh bikini top! The adjustable spaghetti straps ensure your perfect fit, while the alluring front cutout with string details and seashell trim adds a touch of beachy glamour. Pair with the matching bikini bottoms!
Shop Matching Bottoms: Ocean Dreams Seashell Mesh Bikini Bottoms
Fit & Features
- Mesh-lined fabric
- Adjustable spaghetti straps
- Front cutout, strings with seashell trim
- Back cutout with string trim
- Runs true to size
Style Number/Barcode: 07104-000001
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Occasion Satin Cargo Mini Skirt
The perfect stylish satin mini skirt for any occasion! Crafted on silky stretch satin, this skirt features a flattering high-rise waist, a form-hugging fit, dual side flap pockets, and a mini-length hem. Complete the look with a sleek moto jacket and boots!
Fit & Features
- High-rise waist
- Front hidden zipper and hook closure
- Form-hugging fit
- Dual side flap pockets. mini-length hem
- Silky stretch satin-lined fabric
- Stretchy knit shorts lining
- Runs true to size
Style Number/Barcode: 06403-0438
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mentionable Flirt One-Shoulder Asymmetrical Crop Top
For an effortless flirty outfit, pair this one-shoulder crop top with a trendy pair of denim! It features a single shoulder strap, an adjustable side drawstring to let you customize the fit, and an asymmetrical cropped hem on soft knit fabric. Complete the look in a denim midi skirt and sneakers.
Fit & Features
- Soft knit stretchy fabric, bust lining
- One-shoulder neckline
- Side adjustable drawstring
- Asymmetrical cropped hem
- Runs true to size
Style Number/Barcode: 06002-1860
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale