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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Jetset Babe One Shoulder Tropical Maxi Dress
Jetset off on vacation like a babe in this tropical maxi dress! With a flirty and flattering one-shoulder neckline, ruched seams, and a bodycon silhouette, you'll be turning heads. Plus, the side slit and maxi-length hem add a touch of allure. Complete the look in sandals and sunglasses.
Fit & Features
- Tropical palm leaf print, stretchy knit
- One shoulder neckline
- Bodycon silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5702
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Give Me Cozy Half-Zip Fuzzy Knit Crop Sweater
Cozy up in this fuzzy knit sweater for warm cuddles all day and a cute look! The sweater features slouchy long sleeves with ribbed cuffs, a half-zipper front closure, a foldover collar neckline, and a cropped rib hem. Style with high-rise jeans for school or casual weekend plans!
Fit & Features
- Slouchy long sleeves with ribbed cuffs
- Half-zipper front closure
- Foldover collar neckline
- Cropped rib hem
- Fuzzy knit sweater fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1757
Category Name: Vacation Looks
Price: $3.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt
Sweet and flirty, this floral ruched mini skirt will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The skirt features a high-rise elasticized waist, a ruched seam with an adjustable drawstring for a customized fit, a short front slit, and a bodycon silhouette. Style with the matching tie-front top for a day date!
Shop Matching Top: Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top
Fit & Features
- Ditsy floral printed knit fabric, moderate stretch
- High-rise elasticized waist
- Ruched seam with adjustable drawstring
- Short slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1005
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Escape Stiletto Mules
These raffia mule heels bring breezy, sun-soaked energy with breezy midi dresses or cute denim skirts perfect for any sun-soaked day.
Fit & Features
- Stiletto heel
- Square toe
- Braided strap
- Cushioned insole
- Raffia woven material
- Runs true to size
Style Number/Barcode: 07401-000533
Category Name: Vacation Looks
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Weather Faux Fur Bucket Hat
This adorable faux fur bucket hat is a cozy must-have for your cold-weather 'fits! It features a classic bucket hat design composed of an ultra-plush faux fur material with a smooth woven lining. Style with a sherpa-lined jacket for all the comfy vibes this season!
Fit & Features
- Classic bucket hat design
- Short brim
- Faux leather material
- Woven interior
Style Number/Barcode: 07302-1568
Category Name: Vacation Looks
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Classic bucket hat design
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Cold Babe Faux Sherpa Block Heel Booties
Strut like a babe in these cozy faux leather booties! They feature a square-shaped toe, an inner zipper closure, a platform sole, a tall block heel, and a soft faux sherpa trim to help keep you warm on chilly days. Complete the look with a cozy jacket.
Fit & Features
- Square toe
- Inner zipper closure
- Platform sole
- Tall block heel
- Faux sherpa trim
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1681
Category Name: Vacation Looks
Price: $12.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Layer Up Sleeveless Puffer Vest With Pockets
Style up your look in this puffer vest for the chilly season ahead! Featuring a sleeveless design with a standing collar neckline, front zipper closure, and an elasticized cropped hem. Crafted with an insulated nylon woven fabric and hidden side pockets with snap-button closures for extra comfort and warmth. Complete the look in a basic long sleeve top and jeans for a coffee run and errands!
Fit & Features
- Sleeveless standing collar neckline
- Front zipper closure
- Hidden side pockets with snap-button closures
- Elasticized cropped hem
- Insulated nylon woven fabric for warmth
- Puffer design
- Runs true to size
Style Number/Barcode: 06201-0428
Category Name: Vacation Looks
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual And Chill Plaid Shacket
Keep it casual and chill with a shacket that brings those girl-next-door vibes. The shacket features a plaid print, a multi-button down front, two chest pockets, long sleeves with a single-button cuff, and a longline length with a rounded hem. The shacket is composed of a soft faux wool fabric that offers a relaxed fit with a minimal stretch. Complete the look with thigh-high boots.
Fit & Features
- Plaid print
- Collared neckline
- Long sleeves with button cuff
- Multi-button down front
- Two chest pockets
- Longline length, rounded hem
- Faux wool fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1657
Category Name: Vacation Looks
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Better Half Cable Knit One Shoulder Sweater Top
Wrap up in cozy style with this cable knit sweater top perfect for looking effortlessly cute in the chilly season! It features a one-shoulder neckline, a slouchy long sleeve with ribbed cuffs, a cropped hem, and a soft cable knit design. Complete the look in a faux leather mini skirt and boots for a coffee date.
Fit & Features
- One-shoulder neckline
- Slouchy long sleeve, ribbed cuffs
- Cropped hem
- Soft cable knit design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1746
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Golden Hour High-Rise Cargo Wide-Leg Linen Pants
Stroll in these linen wide-leg pants during golden hour on vacation or a weekend by the beach! Designed with a high-rise elasticized waistband and linen fabric, these pants are perfect for all-day wear along with convenient cargo flap pockets and a wide-leg silhouette, you'll feel effortlessly chic and ready for anything. Complete the look with the matching vest and sandals.
Shop Matching Vest: Golden Hour Tie-Front Linen Vest
Fit & Features
- Linen fabric lined with stretchy knit
- High-rise elasticized waistband
- Cargo flap pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0810
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best Feeling Scoop Neck Cutout A-Line Midi Dress
There's nothing better than enjoying a sunny day in this scoop neck midi dress! With adjustable straps and a stretchy smocked bodice with a flirty cutout, this dress offers the perfect look for any occasion. The A-line silhouette and midi-length hem add a touch of playful style. Complete the look with dainty earrings and sandals.
Fit & Features
- Modal blend woven fabric with lining
- Adjustable spaghetti straps
- Scoop neckline
- Stretchy smocked bodice with cutout
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5718
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Chic Acrylic Bangle Bracelet
Effortless style you can slip right on. This acrylic bangle bracelet nails that chunky, laid-back look—perfect for stacking or rocking solo.
Fit & Features
- Acrylic material
- Thick bangle silhouette
- Slip-on design
Style Number/Barcode: 07003-000122
Category Name: Vacation Looks
Price: $4.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Sensation High Waist Pants
Keep it sensational in floral pants this season! The pants feature a high-rise waist, a ditsy floral print, and a wide leg hem. Complete look with the matching crop top.
Shop Matching Crop Top: Floral Sensation Off The Shoulder Top
Fit & Features
- High rise waist
- Wide leg hem
- Ditsy floral print
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06502-0608
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Linked Up Dual Chain Link Belt
Link up with this sassy dual-chain link belt featuring an adjustable lobster clasp closure. Complete the look in denim shorts for any casual occasion!
Fit & Features
- Dual chain link belt
- Adjustable lobster clasp closure
Style Number/Barcode: 07301-1112
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mystic Pearl Press On Nail Kit
Mystify your alluring presence with this press on nail kit including everything you need to achieve a whimsical flair. The exclusive kit offers two sets of pearly press-on nails with a glowing effect for extra shimmer, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look with faux pearl earrings for a date!
Fit & Features
- Press on nail kit
- Two sets of pearly press-on nails, glow effect
- One mini nail file
- One prep pad with easy instructions
- One glue tube
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07307-0184
Category Name: Vacation Looks
Price: $3.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Flirt Floral Mini Dress
Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched detailing, drawstrings at the hem
- Short, form-hugging fit
- Ribbed knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05102-1404
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Paradise Halter Open Back Slit Midi Dress
Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.
Fit & Features
- Slinky knit fabric, smooth stretchy knit lining
- Halter cowl neckline, beaded spaghetti strap tie
- Open back with spaghetti strap tie
- Bodycon silhouette
- Slit accent, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000283
Category Name: Vacation Looks
Price: $32.00 $45.90
On Sale: Yes
Availability: In Stock
Available Color: RED, BROWN
Available Size: XS, S, M
Product Badge:- Sale
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Casual Fave Ribbed Knit Mini Dress
This basic casual ribbed knit mini dress will be a new fave for the season! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a mini-length hem, and a form-hugging silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sandals for a cute everyday vibe.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Mini-length hem
- Form-hugging bodycon fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5086
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Summer Babe Oversized Square Sunglasses
These trendy oversized shades will have you looking like a total summer babe! The sunglasses feature an oversized square-shaped design, thin arms with sleek metal geometric chain-link accents, rubber nose pads for support, and tinted lenses with ombre shading. Style with a crop top, a mini skirt, and sandals.
Fit & Features
- Oversized square-shaped design
- Thin arms, metal geometric chain-link accents
- Rubber nose pads
- Tinted lenses, ombre shading
- 100% UV protection
Style Number/Barcode: 07008-1024
Category Name: Vacation Looks
Price: $3.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seaside Vacay Criss Cross Straw Block Heels
From summer parties to seaside vacays, these straw block heels are a cute essential all season! With an almond toe and crisscross straps adorned with a buckle accent, these straw block heels add a touch of style to your summer look. Complete the look with a matching set.
Fit & Features
- 3.5" Block heel
- Almond toe
- Crisscross straps, buckle strap
- Straw material
- Runs true to size
Style Number/Barcode: 07401-4919
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crossed Over High-Rise Denim Shorts
Designed with the best fit, these high-rise denim shorts are forever flattering! With a form-hugging fit and a cross-over hem that elevates your everyday look.
Fit & Features
- Medium wash denim fabric, slight stretch
- High-rise waist
- Front button and hidden zipper closure, belt loop accents
- Two back pockets
- Form-hugging fit
- Cross-over hem
- Runs true to size
Style Number/Barcode: 06603-0487
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Contemporary Acetate Oval Hoop Earrings
Achieve contemporary style with these oval hoop earrings! Crafted with high-quality acetate, these hoops offer a modern take on a classic design.
Fit & Features
- Acetate design
- Mini hoop trims
- Post-back closure
Earrings are final sale and may not be returned or exchanged
Style Number/Barcode: 07001-000064
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Glow Floppy Straw Hat
Get a stunning glow this summer with this on-trend floppy hat! It features a fitted top, a wide floppy brim, and is composed of a straw-like material with all-over sequin sparkle details and a frayed hem. Complete your beach-ready look with strappy sandals.
Fit & Features
- Fitted top
- Wide floppy brim
- Straw-like material
- Sequin sparkle details
- Frayed hem
Style Number/Barcode: 07302-0301
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep Me Cozy Slouchy Knit Sweater
The perfect chilly day staple! Cozy up in this cute sweater featuring slouchy dolman sleeves, a boat neckline, and a relaxed crop hem on rib-knit fabric. Pair with casual trouser pants to complete the look!
Fit & Features
- Slouchy dolman sleeves
- Boat neckline
- Relaxed crop hem
- Soft rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1522
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free