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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Like A Boss Rhinestone Chain Necklace
Own the room like the boss that you are, in a necklace that makes a statement! Not only is this chain stunning as a stand alone, but you can also style with longer necklaces for a trendy layered look!
- Smooth chain link design
- Partial rhinestone detailing
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0347
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Jetsetter Tropical V Halter Swimsuit
Vacay Mode: On! She works hard and plays harder

Fits & Features
- One Piece Swimsuit
- Halter Neckline With Self Ties At Nape
- Plunging V Neckline
- High Leg Cut
- Cheeky Fit & Coverage
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0145
Category Name: Vacation Looks
Price: $18.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Beauty Floral Skater Dress
You're all about that effortless beauty look. This floral skater dress has a flowy feel and a beyond gorg print that is totally your vibe.
Fit & Features
- Adjustable spaghetti straps
- Back zipper closure
- High square neck
- High waist seam
- Flowy skater skirt
- Floral print
- Chiffon fabric | Lining
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0382
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Polka Dots Swimsuit
Bring on those retro chic vibes with this pretty polka dot one piece that is perfect for lounging poolside!
Fit & Features
- Strapless sweetheart neckline
- Two front cut outs
- Double tie front details
- Covered bottom
- All over polka dot pattern
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0144
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Raw Potential Cropped Denim Jacket
Girl bring on ur full potential, and bring it in style with a cropped denim jacket! Perfectly style with high waist pants and your go-to booties!
Fit & Features
- Collared neckline
- Long sleeves
- Button down center
- Two front pockets
- Cropped raw hemline
- Light wash denim | No stretch
Style Number/Barcode: 06203-0050
Category Name: Vacation Looks
Price: $11.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacay Mode Tie Front Blouse
A suitcase staple! The Vacay Mode blouse is perf for wearing with your denim shorts for a cute, laid back look. All you need is that refreshing marg

Shop Matching Bottoms: Vacay Mode Smocked Mini Skirt
Fits & Features
- Tie Front Closure
- Long Batwing Sleeves
- Crop Hem I Elastic At Back
- Woven Fabric
- Tropical Palm Print
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0566
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Undeniable Charm Gingham Ribbon Halter Crop Top
Make your way looking charming in this halter crop top with a trendy gingham ribbon trim, it's essential for picnics, day dates, and outdoor BBQs!
Fit & Features
- Woven fabric, bust knit lining
- Halter V-neckline with gingham ribbon trim
- Stretchy smocked back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-000013
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Sweet Clear Sandals
Simple, sweet, and clean. These sandals are an everyday go-to!
- Open almond toe
- Thick clear pvs strap
- Neutral shiny lining
- Flat sole
Style Number/Barcode: 07404-0543
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Fluttering Butterfly Jelly Sandals
Add a little magic to your look when you accent with an iridescent butterfly, and a jelly finish!
- Thong style sandal
- Iridescent butterfly accent
- Adjustable pin buckle closure
- Flat sole
- Composed of jelly material
Style Number/Barcode: 07404-0542
Category Name: Vacation Looks
Price: $10.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spice Things Up V-Neck Cutout Skater Dress
Casual gets a sultry upgrade with this short skater dress perfect for showers and birthdays! This flirty skater dress boasts flowy sleeves, a front and back V-neckline, and a cutout bodice for an alluring look. The gauze fabric adds breezy comfort while the skater silhouette and short length keep you on-trend. Complete the look in strappy wedges.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- V-Neckline front and back
- Cutout bodice, elasticized straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5419
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lavish Lifestyle Iridescent Jewel Jelly Sandals
Live that lavish lifestyle when you step out in these gleaming jelly sandals fit for a princess!
- Thong style almond toe
- Open design
- Iridescent rhinestone embellishments
- Adjustable ankle closure
- Jelly flat sole
Style Number/Barcode: 07404-0120
Category Name: Vacation Looks
Price: $10.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love Affair Textured Off Shoulder Crop Top
YASSS
We've got heart eyes for this cute AF off-shoulder top! Don't forget to add to cart the matching skirt! Shop Matching Skirt: Love Affair Textured Mini Skirt
Fits & Features
- Ruffle-Trim Off Shoulder Neckline & Cuffs
- Ties At Keyhole Opening
- Smocked Back
- Quarter Length Sleeves
- Cropped Hem
- Woven Textured Fabric
- Plenty Of Stretch
Style Number/Barcode: 06001-2482
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Affair Textured Mini Skirt
YASSS
We've got heart eyes for this cute AF mini skirt! Don't forget to add to cart the matching crop top! Shop Matching Top: Love Affair Textured Off Shoulder Crop Top
Fits & Features
- High Rise, Elastic Waistband
- Mini Length Silhouette
- Smocked At The Back
- Woven Textured Fabric
- Form Hugging Fit I Plenty Of Stretch
- No Zipper
Style Number/Barcode: 06401-0212
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fave Floral Mesh Duster
Your new fave floral duster for sure. With its airy, lightweight mesh fabric, you'll want to layer it over all of your cute looks.
Fit & Features
- Long fitted sleeves
- Open front
- Floor length hem
- Sheer mesh fabric
- Floral print
- Plenty of stretch
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06202-0054
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shady Lady Ombre Aviator Sunglasses
Shade the hate when you hide behind these ever so trendy geometrical aviators! Pair with a panama hat when ur out having some fun in the sun!
- Golden frame
- Geometrical aviator design
- 100% UV protection
- Ombre lenses
- Straight across brow bar
Style Number/Barcode: 07008-0685
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Radiant Rhinestone Door Knocker Earrings
Dazzle them with these radiant rhinestone door knocker earrings baby! They feature a gorgeous rhinestone embellished design that will add the perfect amount of sparkle to your look. Style these trendy earrings with your special night out dress, or even pair with a faux leather jacket.
Fit & Features
- Large circular post
- Door knocker design
- Rhinestone embellished
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0338
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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You Have My Heart Necklace
This adorable dainty pendant necklace definitely has our hearts!
- Small heart outline pendant
- Chain link
- Lobster clasp closure
Style Number/Barcode: 07002-0322
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Six Pack Trendy Cross Rings
Make your look all the more trendier by accessorizing with these cross rings!
- Six pack of both regular and midi various rings
- Two flat metal rings
- Four cross shape rings | Three with rhinestone detailing
Style Number/Barcode: 07004-0055
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Six Pack Heart And Rhinestone Stud Earrings
Fall head over heels in love with this six pack of heart and rhinestone stud earrings!
- Six various stud earrings
- Three differing heart shaped studs | Heart outline, mini heart studs, and heart drop earrings
- Three varying shaped rhinestone studs | linear rhinestone earrings, simple oval studs, and cluster rhinestone earrings
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0325
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mini Bar Double Row Necklace
Add a dainty touch to your lewk hunny! This simple necklace will amp up your look in a subtly beautiful way, whether your look is silver, or gold, we are here for it!
- Double row design
- Mini bar drop pendant
- Lobster clasp closure
Style Number/Barcode: 07002-0317
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Top Doll Chain Coin Pendant Necklace
Keep a sleek and sultry look when you add in a layered pendant necklace!
- Double row design
- Snake chain
- Sleek coin pendants
- Lobster clasp closure
Style Number/Barcode: 07002-0318
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Queen Of Hearts Ring Set
You are our sweetheart! This set of rings is an adorable way to show off ur soft side, with a little bling and a little gold!
- Set of five rings
- Three rhinestone designs
- One sleek design
- One sleek dangling charm design
Style Number/Barcode: 07004-0053
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love In Lace Scalloped Bra
Get that loved up look in irresistible lace! This sexy bra features partially lined demi cups with underwire, adjustable straps, a scalloped lace trim throughout and an adjustable hook clasp closure. Be sure to pick up the matching panties to complete your look!
Black: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
White: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
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: 07107-0290
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Level Up Rhinestone Spiral Sandals
Level up your glamorous side in these statement-flat sandals perfect for semi-formal and dressy events! They feature an almond toe, rhinestone embellished toe and spiral ankle straps, and a faux leather footbed with rhinestone trim. Complete the look with a chic ring set.
Fit & Features
- Almond toe
- Rhinestone embellished toe and spiral ankle straps
- Faux leather footbed with rhinestone trim
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1121
Category Name: Vacation Looks
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale