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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Glam Life Off The Shoulder Gauze Romper
Live that glam life with a romper that showcases your style! The romper features an elastic off-the-shoulder neckline, long bell sleeves, a tie waist belt, and wide-leg shorts. Complete look with wedges.
Fit & Features
- Elastic off the shoulder neckline
- Long bell sleeves
- Tie-waist belt
- Wide leg shorts
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0126
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Hour Wide Leg Pants Energy
She’s luxe, bold, and lowkey lethal. These tropical wide-leg pants brings the heat wherever you wear her—beach club or rooftop takeover. Pair with the matching top.
Shop Matching Top: Golden Hour Tube Top Energy
Fit & Features
- Tropical print, stretchy knit fabric
- Mid-rise waist
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000032
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Faux Leather Criss-Cross Braided Sandals
Bring the glamour with sandals that showcase trendy details! The sandals feature a slip-on design, an open square toe, wide braided criss-cross straps. Sandals are composed of a faux leather material. Complete the look with a basic tee and cutoff shorts.
Fit & Features
- Slip-on design
- Open square toe
- Wide braided criss-cross straps
- Faux leather material
Style Number/Barcode: 07404-0712
Category Name: Vacation Looks
Price: $13.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Babe Faux Leather Sandals
You'll look like a total trendy babe when you style up your look with these sandals! They feature a round open toe with double-banded straps and a slide-on design. The sandals have a flat sole and are composed of a sleek faux leather material. Pair these shoes with mom jeans and a graphic tee.
Fit & Features
- Round open toe
- Double-banded straps
- Slide-on design
- Flat sole
- PU material
- Runs true to size
Style Number/Barcode: 07404-0721
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Babe Faux Leather Cork Block Heels
Keep it trendy with heels that slay your look! The heels feature an open back, an adjustable ankle strap, a T-strap accent, an open almond toe with a caged design, a cork wedge, and a block heel. Complete look with a ribbed midi dress.
Fit & Features
- Open back
- Adjustable ankle strap
- T-strap accent
- Open almond toe with caged design
- Cork platform and block heel
- Faux leather
Style Number/Barcode: 07401-2983
Category Name: Vacation Looks
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Step Up Your Style Anklet Set
Step up your style with this trendy set of anklets! The pack features four anklets with dainty and thick metal chain designs, one featuring a cute butterfly charm. Style all four anklets together with your fave pair of sandals.
Fit & Features
- Set of four anklets
- Dainty to thick metal chain designs
- Butterfly charm
Style Number/Barcode: 07003-0206
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dainty Detailed Lace Crop Top
You'll fall in love with the dainty details of this pretty lace crop top! It features an off-the-shoulder neckline with a ruffled trim, short fitted sleeves, a double tie-front design, an open front, and a cropped, form-hugging fit. The sheer lace fabric has a front lining. Style this top with cutoff denim shorts and sandals.
Fit & Features
- Off-the-shoulder neckline, ruffled trim
- Short fitted sleeves
- Double tie-front design
- Open front
- Cropped, form-hugging fit
- Sheer lace fabric, front lining
- Runs true to size
Style Number/Barcode: 06001-3306
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovely In Linen Sleeveless Skater Dress
Get a lovely look this season in this flowy linen skater dress! It features a sleeveless bodice, tank shoulder straps, a V-neck and back, a high waist with trendy bar cutouts on each side, and a flirty skater silhouette. Style this dress with sandals for a breezy vacay outfit.
Fit & Features
- Tank shoulder straps
- V-neck and back
- High waist, bar cutouts on each side
- Flowy skater silhouette
- Linen and gauze fabric
- Runs true to size
Style Number/Barcode: 05102-0241
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Status Quilted Faux Leather Sandals
Elevate your chic status with these must-have slide-on sandals. They feature an open round toe, a thick criss-cross strap design, a flat sole, and a quilted faux leather material. Style these sandals with a casual dress and chic shades.
Fit & Features
- Open round toe
- Thick criss-cross strap design
- Flat sole
- Quilted faux leather material
- Runs true to size
Style Number/Barcode: 07404-0801
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shell We Dance Crochet Hanky Top
Your boho era just called and said to wear this. This crochet hanky top brings flirty vibes with a strapless fit and fringe shell trim, perfect for beach days, brunch dates, or dancing barefoot in the sand.
Fit & Features
- Crochet fabric, stretchy knit lining
- Strapless tube neckline
- Hanky hem with shell trim
- Runs true to size
Style Number/Barcode: 06005-000078
Category Name: Vacation Looks
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Glam Platform Cork Heels
Get a casual glam look this summer season in these adorable cork heels! They feature an open round toe, a thick criss-cross strap design, an adjustable ankle strap, and a cork platform and block heel. Style these trendy heels with a floral dress and chic shades.
Fit & Features
- Open round toe
- Thick criss-cross strap design
- Adjustable ankle strap
- Open back
- Cork platform and block heel
- Runs true to size
Style Number/Barcode: 07401-2984
Category Name: Vacation Looks
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless And Chic Eyelet Mini Dress
Effortless and chic, this eyelet mini dress is the perfect addition to your summer wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with strappy sandals.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Short, form-hugging fit
- Sheer eyelet fabric, full lining
- Runs true to size
Style Number/Barcode: 05102-1275
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Beauty Flare Pants
You'll be a total bohemian beauty in these on-trend flare pants! They feature a high-rise waist, a form-hugging fit, a flared-out hem, and an all-over bohemian-inspired print. Style these knit pants with a basic crop top and sandals.
Fit & Features
- High-rise waist
- Form-hugging fit
- Flared-out hem
- Bohemian-inspired print
- Knit fabric
- Runs true to size
Style Number/Barcode: 06502-0596
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Plunging Into Basics Surplice Jumpsuit
Take the plunge into a basic jumpsuit that keeps it part casual, part stylish. The jumpsuit features a sleeveless wrap V-neckline with spaghetti straps, an elastic waistband, hidden side pockets, and a straight leg fit with an elastic hem. The jumpsuit is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules and statement earrings.
Fit & Features
- Sleeveless wrap V-neckline
- Spaghetti straps
- Elastic waistband
- Hidden side pockets
- Straight leg fit with elastic hem
- Lightweight woven fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0202
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Elevated Basics High Waist Paperbag Shorts
Elevate your basic fits with paper bag shorts that are so on-trend! The shorts feature a high-rise paper bag waist, a hidden zipper front, a tie waist belt with belt loops, slant pockets, and cuffed hem. Complete look with a blouse and denim jacket for a cute casual outfit.
Fit & Features
- High-rise paper bag waist
- Hidden front zipper and hook and bar closure
- Tie-waist belt with belt loops
- Slant pockets, cuffed hem
- Woven fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06403-0158
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glow N' Shimmer Low Rise Bikini Bottoms
Chase that glow in these shimmery bikini bottoms! They feature a low rise waist and a cheeky fit. They are composed of a glitter lurex fabric that offers a form hugging fit. Complete your vacation outfit with the matching bikini top.
Shop Matching Bikini Top: Glow N' Shimmer Bikini Top
Fit & Features
- Low-rise waist
- Cheeky fit
- Glitter lurex
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0517
Category Name: Vacation Looks
Price: $5.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Era V-Neck Ruffled Romper
Enter your sweet girl era in this eyelet romper perfect for brunch, graduations, or shower celebrations! The V-neck and form-hugging bodice create a flattering silhouette, while the ruffled hem adds a playful touch.
Fit & Features
- Eyelet knit fabric
- V-neckline
- Spaghetti straps
- Form-hugging bodice
- Ruffled skirt overlay, shorts lining
- Runs true to size
Style Number/Barcode: 06503-000032
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glow N' Shimmer Bikini Top
Chase that glow in this shimmery bikini top! It features a plunging sweetheart neckline, demi-cups, underwire, adjustable spaghetti straps, and a slide-hook fasten closure. Complete your vacation outfit with the matching bikini bottoms.
Shop Matching Bikini Bottoms: Glow N' Shimmer Low Rise Bikini Bottoms
Fit & Features
- Sleeveless sweetheart neckline
- Demi-cups
- Underwire
- Adjustable spaghetti straps
- Slide-hook fasten closure
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0368
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Stunner Floral Skater Dress
Bring the charm in this stunning floral skater dress. It features ruffle detail shoulder straps, a wrap-front V-neckline with a ruffle overlay, an open back with a tie closure, a waist tie accent, and a flirty skater skirt with a tiered ruffle design. Style this chiffon dress with hoop earrings and sandals.
Fit & Features
- Ruffle detail shoulder straps
- Wrap-front V-neckline, ruffle overlay
- Open back, tie closure, back zipper and hook and eye closure
- High waist, tie-front
- Skater skirt, tiered ruffle design
- Floral chiffon fabric, knit lining
- Runs true to size
Style Number/Barcode: 05101-1004
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Vibes Tie Dye Mini Dress
Channel retro vibes with a mini dress that keeps it super cute! The dress features a sleeveless crew neckline, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with clear mules to let this print take center stage!
Fit & Features
- Sleeveless
- Crew neckline
- Tie-dye print
- Mini length silhouette
- Brushed knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1096
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stand Out In Stripes Tie Front Crop Top
Stand out in stylish stripes with a top that elevates your casual outfits. The top features a striped pattern, plunging V-neckline with tie-front, quarter length sleeves with elastic hem, and a cropped hem. Complete look with high waist jeans.
Fit & Features
- Plunging V-neckline
- 3/4 sleeves
- Striped pattern
- Tie Front
- Cropped hem
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-0888
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seeing Stars Necklace Multi Pack
Channel a starry-eyed look with this cute necklace pack! The pack includes three necklaces with galactic-inspired designs. One necklace features a snake chain, one features a crescent moon charm, and one necklace features a starburst-designed charm with a rhinestone center accent. Complete look with a crop top and shorts.
Fit & Features
- Pack includes three necklaces
- Snake chain
- Crescent moon
- Starburst design with rhinestone center
- Lobster clasp closure
Style Number/Barcode: 07002-0725
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sippin' On Henny Cap
Let this cap say it all! The cap features a traditional baseball cap design and a script that reads "Henny" with olive branch accents. Complete look with a crop top and cutoff shorts for a laid-back look.
Fit & Features
- Baseball cap design
- "Henny" script
- Olive branch accent
- Adjustable strap
Style Number/Barcode: 07302-0314
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Allure Ruched Mini Skirt
Let those tropic vibes allure you in with this cute mini skirt! The skirt features a high-rise waist, a tropical palm leaf print, ruched side seams, and a mini-length silhouette. Complete look with the matching crop top and wedges that will have you vacay ready!
Shop Matching Crop Top: Tropical Allure Mesh Crop Top
Fit & Features
- High rise waist
- Tropical palm leaf print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0400
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free