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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Sunday Strolls Floral Tie Front Top
Take a stylish stroll to brunch in this floral tie-front top featuring adorable short puff sleeves, a plunge V-neckline, and a cropped hem. Complete the look in a denim mini skirt.
Fit & Features
- Short puff sleeves, elasticized hems
- Plunge V-neckline
- Tie-front detail
- Cropped hem
- Floral print
- Lightweight woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1322
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Last Night Of Vacay Lace-Up Top
Go out with a sizzle in this tropical crop top on your vacay! It features a sleeveless, mock neck, and a sexy front cutout with lace-up closure. Complete the look in the matching skirt.
Shop Matching Skirt: Last Night Of Vacay Lace-Up Skirt
Fit & Features
- Sleeveless, mock neck
- Front cutout with lace-up closure
- Cropped hem
- Tropical print lined-knit fabric
- Runs true to size
Style Number/Barcode: 06001-3990
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Last Night Of Vacay Lace-Up Skirt
Go out with a sizzle in this tropical mini skirt on your vacay! It features a high-rise waist, bodycon silhouette, and a side cutout with lace-up detail. Complete the look in the matching top.
Shop Matching Top: Last Night Of Vacay Lace-Up Top
Fit & Features
- High-rise waist
- Side cutout with lace-up
- Bodycon silhouette
- Mini-length hem
- Tropical print lined-knit fabric
- Runs true to size
Style Number/Barcode: 06501-0590
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Here Comes The Sun Strapless Ruffled Mini Dress
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The short tube dress features ruched sides and a ruffled hem, adding a playful touch to the bodycon silhouette.
Fit & Features
- Double-lined brushed knit fabric, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Bodycon silhouette
- Mini-length tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5784
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rhine Drops Layered Lariat Choker
It's raining rhine! Add a glam touch to your formal wear with this layered lariat choker featuring a three-row design, rhinestone drops, and dainty chain links with a lobster clasp closure. Complete the look in sleek heels.
Fit & Features
- Layered three-row design
- Rhinestone drops
- Dainty chainlinks
- Lobster clasp closure
Style Number/Barcode: 07002-1144
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glitzy Poolside Vibes Maxi Skirt
Showcase fab glitzy poolside vibes with this sheer mesh maxi skirt. It features a high-rise banded waist, a fitted maxi-length silhouette with a sultry thigh-high side slit, and all-over rhinestone embellishment. Style this cover-up over your fave bikini and complete the look with a floppy hat.
Fit & Features
- High-rise banded waist
- Fitted maxi-length silhouette
- High side slit
- Sheer mesh fabric
- All-over rhinestone embellishment
- Runs true to size
Style Number/Barcode: 06501-0675
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Boho Flair Tulip Pants
Bring that effortless boho flair to your casual summer look with these trendy tulip pants. They feature a high-rise fitted waist, a wide-leg silhouette with high front slits, a flowy, relaxed fit, and an all-over bohemian-inspired border print. Style these pants with a crop top and sandals.
Fit & Features
- High-rise fitted waist
- Wide-leg silhouette, high front slits
- Relaxed fit
- Bohemian-inspired border print
- Lightweight woven fabric
- Runs true to size
Style Number/Barcode: 06302-0657
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Vibes Wide Leg Jumpsuit
Transport to a tropical paradise with a jumpsuit that is vacay ready! The jumpsuit features a tropical floral print, a sleeveless square neckline, and a wide-leg pant. The jumpsuit is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and sunnies.
Fit & Features
- Tropical floral print
- Sleeveless square neckline
- Wide leg pant
- Sleek knit lined fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0754
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Fleek Cat Eye Sunglasses
Nail that cat-eye trend without having to master eye liner! These sunglasses feature a classic cat-eye silhouette, plastic frame, and gradient lenses. Complete the look in a casual jumpsuit for a weekend getaway.
Fit & Features
- Classic cat-eye silhouette
- Plastic frame
- Gradient lenses
- 100% UV protection
Style Number/Barcode: 07008-0940
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Retro Getaway Mesh Mini Dress
Make sure to pack this retro-fab mini dress for your next desert getaway! It features a sleeveless crew neckline, tank shoulder straps, cinched detailing down one side with an adjustable drawstring, and a short, form-hugging fit. The sheer mesh fabric features an all-over paisley print pattern. Style this dress over the matching bikini with cat-eye sunglasses.
Shop Matching Bikini Top: Retro Getaway Bikini Top
Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms
Shop Matching Headwrap: Retro Getaway Mesh Headwrap
Shop Matching Skirt: Retro Getaway Mesh Mini Skirt
Shop Matching Duster: Retro Getaway Long Mesh Duster
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Cinched detailing down one side, adjustable drawstring
- Mini-length, form-fitting silhouette
- Paisley print
- Sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4028
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Clearance
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So Extra Glam Rhinestone Bucket Hat
Elevate your festival fit in this extra glam bucket hat featuring all-over rhinestone embellishments and a short brim. Complete the look in an edgy-cute graphic tunic top.
Fit & Features
- All-over rhinestone embellishments
- Short brim
- Classic bucket hat styling
Style Number/Barcode: 07302-0642
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Island Vibes Crop Top
Showcase dreamy island vibes in this lightweight chiffon crop top! It features a sleeveless square neckline, adjustable spaghetti straps for a customizable fit, a cropped, form-hugging silhouette, and an all-over tropical palm leaf print. Style this cute top with the matching kimono and shorts.
Shop Matching Kimono: Dreamy Island Vibes Chiffon Kimono
Shop Matching Bottoms: Dreamy Island Vibes Tie-Waist Shorts
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper closure
- Cropped, form-hugging fit
- Tropical palm leaf print
- Chiffon fabric
- Runs true to size
Style Number/Barcode: 06003-1608
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dreamy Island Vibes Chiffon Kimono
Showcase dreamy island vibes in this airy chiffon kimono! It features flowy three-quarter-length kimono-style sleeves, an open front, a relaxed fit, and an all-over tropical palm leaf print. Style this lightweight layer with the matching crop top and shorts.
Shop Matching Top: Dreamy Island Vibes Crop Top
Shop Matching Bottoms: Dreamy Island Vibes Tie-Waist Shorts
Fit & Features
- Flowy three-quarter-length kimono-style sleeves
- Open front
- Relaxed fit, subtle high-low hem
- Tropical palm-leaf print
- Semi-sheer chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1224
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Island Vibes Tie-Waist Shorts
Showcase dreamy island vibes in these lightweight high-rise shorts! They feature a tie-front design, a back-smocked waistband for comfortable wear, a fitted silhouette, and an all-over tropical palm leaf print. Style these cute shorts with the matching kimono and crop top.
Shop Matching Kimono: Dreamy Island Vibes Chiffon Kimono
Shop Matching Top: Dreamy Island Vibes Crop Top
Fit & Features
- High-rise waist, back-smocked waistband
- Tie-front, pleated detailing
- Fitted silhouette
- Tropical palm leaf print
- Chiffon lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06403-0206
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish And Smocked Crop Top
This smocked crop top will give your summer look a stylish vibe! It features a sleeveless V-neckline, spaghetti straps, and a cropped, form-hugging fit. Complete the outfit with the matching mini skirt and chic mules.
Shop Matching Bottoms: Stylish And Smocked Mini Skirt
Fit & Features
- V-neckline
- Spaghetti straps
- Cropped, form-hugging fit
- Smocked knit fabric
- Runs true to size
Style Number/Barcode: 06001-3287
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Town Large Straw Floppy Hat
Heading into town? Shade yourself from the sun in style wearing this large straw floppy hat. It features a wide brim and two-tone striped design. Complete the look in a darling matching set.
Fit & Features
- Large design
- Wide floppy brim
- Two-tone striped design
- Straw material
Style Number/Barcode: 07302-0515
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Holiday In The Sun Smocked Crop Top
If ya got it flaunt it on holiday! Sass up your look in this smocked crop top featuring a sleeveless sweetheart neck, sleek elasticized spaghetti straps, and a flirty front cinch accent. Complete the look with the matching mini skirt.
Shop Matching Bottoms: Holiday In The Sun Smocked Mini Skirt
Fit & Features
- Sleeveless, sweetheart neck
- Elasticized spaghetti straps
- Front cinch accent
- Cropped hem
- Smocked fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3756
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good At Being Bad Lace Hot Shorts
Earn style cred in these lace hot shorts with frilly ruffles and a cheeky fit. Pair with the matching top.
Fit & Features
- Lace fabric
- Low-rise waist
- Frilly ruffled design
- Cheeky fit
- Runs true to size
Shop The Matching Top: Good At Being Bag Lace Crop Top
Style Number/Barcode: 06503-000027
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Lace fabric
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Holiday In The Sun Smocked Mini Skirt
If ya got it flaunt it on holiday! Sass up your look in this smocked mini skirt featuring a high-rise waist and a mini-length, curve-hugging silhouette. Complete the look with the matching crop top.
Shop Matching Top: Holiday In The Sun Smocked Crop Top
Fit & Features
- High-rise waist
- Mini-length, form-fitting silhouette
- Smocked knit-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0543
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Retro Wide-Leg Pants
Showcase a trendy retro vibe in these chic palazzo pants. They feature a high-rise smocked waist, a wide-leg silhouette, and a relaxed fit. The lightweight woven fabric features a fab all-over geometric pattern. Style with the matching bandeau top.
Shop Matching Top: So Retro Halter Bandeau Top
Fit & Features
- High-rise smocked waist
- Wide-leg silhouette
- Relaxed fit
- Geometric pattern
- Unlined woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0636
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Retro Halter Bandeau Top
Showcase a trendy retro vibe in this alluring bandeau top. It features a sleeveless halter neckline with spaghetti straps, a center O-ring accent at the bust, and a tie-back strap design. The lightweight woven fabric features a fab all-over geometric pattern. Style with the matching wide-leg pants.
Shop Matching Bottoms: So Retro Wide-Leg Pants
Fit & Features
- Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
- Center O-ring detail
- Tie-back strap design
- Cropped, form-hugging fit
- Geometric pattern
- Woven fabric, front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4123
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Retro Getaway Bikini Top
Make sure to pack this retro-fab bikini top for your next desert getaway! It features a basic triangle design with padded cups, halter spaghetti straps, and lower tie-back spaghetti straps. The top features an all-over paisley print pattern. Style with the matching bikini bottoms and cat-eye sunglasses.
Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms
Shop Matching Headwrap: Retro Getaway Mesh Headwrap
Shop Matching Skirt: Retro Getaway Mesh Mini Skirt
Shop Matching Dress: Retro Getaway Mesh Mini Dress
Shop Matching Duster: Retro Getaway Long Mesh Duster
Fit & Features
- Triangle design
- Removable padding
- Halter spaghetti straps, tie at the back of the neck
- Lower tie-back spaghetti straps
- Paisley print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0641
Category Name: Vacation Looks
Price: $20.90
Availability: Out of Stock
Product Badge:- Sale
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Tight Race Seamless Biker Romper
Stay comfy while running errands in this stylish seamless biker romper featuring a sleeveless, boat neckline, adjustable spaghetti straps, and a bodycon silhouette. Composed of stretchy rib-knit fabric. Finish the look in an oversized plaid shacket and a dad hat.
Fit & Features
- Sleeveless, boat neckline, adjustable spaghetti straps
- Biker-length shorts
- Bodycon silhouette
- Stretchy rib-knit fabric
- Seamless design for comfort
- Fits true to size
Style Number/Barcode: 07103-0750
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Instinct Snake Charm Anklet
Eyeing this anklet? It must be a natural instinct of yours to like nice things! It features a two-row rhinestone design and a snake charm with a lobster clasp closure. Complete the look in a chic midi dress for your next vacation.
Fit & Features
- Two-row rhinestone design
- Snake charm
- Lobster clasp closure
Style Number/Barcode: 07003-0334
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale