Vacation Looks
Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.
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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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Flirt on Repeat Ruffle Skort
Made to twirl, tease, and totally steal the spotlight. This ruffle mini skort is flirty with just enough edge—and yes, it comes with built-in shorts so you can actually move.
Fit & Features
- Abstract print, mesh fabric, stretchy knit shorts lining
- Mid-rise waist
- Form-hugging fit
- Ruffled mini skirt overlay
- Runs true to size
Style Number/Barcode: 06503-000114
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cozy Bliss Faux Fur Bucket Hat
Fit & Features
- Oversized bucket design
- Faux fur fabrication
Style Number/Barcode: 07302-1734
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Luxe Rhinestone Charm Belly Chain
This dainty rhinestone charm belly chain is dotted with shimmering charms—perfect for layering or letting it shine solo on your next night out.
Fit & Features
- Rhinestone charms
- Dainty chain
- Lobster clasp closure
Style Number/Barcode: 07002-000190
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Party Hour Rhinestone Beer And Lime Earrings
Dive into fun with these rhinestone beer and lime earrings. Featuring a lime slice post and sparkling beer bottle design, these earrings are your perfect party pals. Cheers to style!
Fit & Features
- Lime slice post
- Hanging beer bottle design
- Mini rhinestone embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2321
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Shady Baby Oval Sunglasses
Serving throwback attitude with a modern twist—these cat eye sunglasses are the ultimate finishing touch to any fit. Whether it’s brunch, beach, or just a vibe check, they’ll have you looking instantly cooler.
Fit & Features
- Oval round frame
- Gradient tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000039
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: NS
Product Badge:- New Arrival
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Chasing Sunshine Crochet Wedges
These crochet wedge mules serve beachy vibes with an elevated twist, perfect for brunch, shower celebrations, or dinners al fresco.
Fit & Features
- Square toe
- Wide strap
- Wedge sole
- Crochet material
- Runs true to size
Style Number/Barcode: 07406-000028
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: NUDE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Pretty Aura Floral Print Strapless Crop Top
Nail your look with cute jeans and this floral print strapless crop top. Featuring a V-cut insert and ruching, this flirty piece hugs your curves and brings all the vibes.
Fit & Features
- Lined knit fabric with plenty of stretch
- Large floral print
- Strapless neckline with V-cut insert
- Ruching
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-5552
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Side Leopard Halter Crop Top
Serving up fierce with a side of flirty, this halter crop top is pure attitude. The hoop inserts bring the drama while the fit keeps it effortlessly cool for nights out or rooftop hangs.
Shop The Matching Bottoms: Wild Side Leopard Wide-Leg Pants
Fit & Features
- Soft stretch knit fabric with leopard print
- Halter neckline with hoop insert details, tie closure
- Cropped silhouette with open back and tie closure
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000265
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Coastal Chic Starfish Dangle Earrings
Fit & Features
- Dangle design
- Textured starfish charm
- Fish hook closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2329
Category Name: Vacation Looks
Price: $3.97 $7.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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: $13.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
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Cutely Charming One-Shoulder Crop Top
Go ahead and strut your cute and charming self in this sleeveless crop top to elevate your basics collection! It boasts a one-shoulder neckline with a cinch detail, and a fitted crop hem on stretchy rib knit fabric. Complete the look in a denim midi skirt and sandals!
Fit & Features
- Stretchy rib knit fabric
- One-shoulder neckline
- Tank strap with cinch detail
- Fitted crop length hem
- Runs true to size
Style Number/Barcode: 06002-1909
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Bloom Floral Ruffle Skater Dress
Serving soft-girl romance with a side of sass, this floral halter mini dress is made for twirls and double takes. Wear it when you want compliments on repeat.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch, floral print
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Ruching, drop waist
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000297
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- New Arrival
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Fierce Allure Leopard Print Mesh Maxi Dress
Flaunt a fierce allure in this curve-hugging leopard print maxi dress! The airy sheer mesh fabric lined with knit offers plenty of stretch and showcases a leopard print pattern for a sultry-chic vibe. The long dress features a sleeveless V-neckline, spaghetti straps, a form-fitting silhouette to accent your gorgeous curves, and a maxi-length hem. Style with strappy mules for a rooftop happy hour.
Fit & Features
- Leopard print
- Sheer mesh fabric with knit lining, plenty of stretch
- V-neckline
- Spaghetti straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-3328
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Arm Candy Stacking Bangle Bracelet Set
Because one bracelet is never enough. This stacking bangle set mixes bold and sleek textures so you can layer up for that effortlessly luxe vibe.
Fit & Features
- Mixed metal
- Assorted bangle silhouettes
- Smooth, textured, and braided designs
Style Number/Barcode: 07003-000079
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top
Wildly sultry is exactly how you'll look in this leopard rose mesh crop top on a night out! The flared long sleeves and V-neckline with tie closure give a playful touch, while the center slit adds a touch of allure. The cropped length and striking leopard rose print make this top a must-have for any bold fashionista. Complete the look with the matching skirt.
Shop Matching Bottoms: Wildy Sultry High Rise Leopard Floral Maxi Skirt
Fit & Features
- Leopard rose print, sheer mesh fabric, moderate stretch
- Flared long sleeves
- V-neckline
- Tie-front closure and center slit
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-0472
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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Edgy Stretch Resin Bracelet
A little shine, a lot of style. This resin stretch bracelet with sleek metal trim is the low-effort way to elevate any outfit—stack it up or let it stand alone.
Fit & Features
- Smooth resin material
- Stretch elastic fit
- Polished metal trim accents
- Lightweight and comfortable
- Please note color varies
Style Number/Barcode: 07003-000110
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: BROWN, GREEN
Available Size: NS
Product Badge:- New Arrival
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Shape Shift Resin Square Bangle Bracelet
Because your stack deserves a statement piece. This resin square bangle adds a bold, modern twist to your wrist game—wear it solo or layer for instant cool-girl points.
Fit & Features
- Smooth resin material
- Square bangle design
- Solid structured fit
- Lightweight and comfortable
Style Number/Barcode: 07003-000113
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
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Wildy Sultry High Rise Leopard Floral Maxi Skirt
Wildly sultry is exactly how you'll look in this leopard rose mesh maxi skirt on a night out! The skirt boasts a flattering high-rise waist complimented by a bodycon silhouette that accentuates your curves along the midi-length hem. Complete the look with the matching top.
Shop Matching Top: Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top
Fit & Features
- Leopard floral print, mesh fabric lined with stretchy knit
- High-rise waist
- Hip-hugging fit
- Maxi-length
- Runs true to size
Style Number/Barcode: 06501-1052
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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Party Diva Cropped Rhinestone Halter Top
A cropped rhinestone halter top that'll inspire your next going-out look! It features a sultry plunge cowl neckline and a partially open back that turns heads. Pair with jeans.
Fit & Features
- Sheer mesh fabric with knit lining, moderate stretch
- Studded rhinestones
- Plunging halter neckline, cowl bust
- Mini bar strap at bust
- Halter neck ties, partially open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-5498
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: NUDE, BURGUNDY
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Serving Vibes Halter Crop Top
This halter crop top will serve major stunning vibes for cocktails and dinner! It is designed with ruched side seams and a fitted crop hem that accentuates your figure.
Fit & Features
- Sheen knit fabric, sewn-in knit lining, high stretch
- Halter plunge neckline with tie closure
- Side ruched seams
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000174
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: ORANGE, IVORY, MOCHA, WINE
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Sultry Fave Halter Cowl Neck Floral Maxi Dress
You'll always embody sultriness in this floral mesh maxi dress perfect for weddings or cocktail parties! The halter cowl neckline with tie adds a touch of charm, while the form-hugging silhouette highlights your curves. The maxi-length hem and floral print mesh fabric bring an elegant and romantic touch. Complete the look with rhinestone earrings and a clutch.
Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Halter cowl neckline with tie
- Form-hugging silhouette
- Maxi-length
- Runs true to size
Style Number/Barcode: 05101-3331
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom With A View Floral Mini Skirt
Wherever your travels take you, this floral mini skirt is here to make your view that much prettier! Designed to flatter, this skirt has a sleek mid-rise waist and bodycon silhouette that highlights your figure. Pair with the matching top to complete the look.
Fit & Features
- Floral print, mesh fabric, sewn-in knit lining, moderate stretch
- Mid-rise waist
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Shop The Matching Top: Bloom With A View Floral Tube Top
Style Number/Barcode: 06501-000048
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Stacked To Perfection Beaded Stretch Bracelets
Level up your stack game with zero effort. These beaded stretch bracelets are giving luxe layering vibes with that cool-girl ease you love.
Fit & Features
- Multi-pack beaded bracelets
- Varying sizes
- Stretchy design
Style Number/Barcode: 07003-000051
Category Name: Vacation Looks
Price: $13.90
Availability: Out of Stock
Product Badge:- Ships Free
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Easygoing Chic Puff Sleeve Tie Front Top
You'll feel easygoing and chic in this linen-like top for any weekend plans or on vacay! With its playful puff sleeves and breezy open front design featuring dual tie-fronts, this top is the perfect addition to your summer wardrobe. Pair with the matching skort.
Fit & Features
- Linen-like woven fabric, sewn-in knit lining
- Puff short sleeves
- Open front design, dual tie-front
- keyhole back with button closure, stretchy smocked panel
- Mid-length hem
- Runs true to size
Shop The Matching Skort: Easygoing Chic High-Rise Wrap Tie Skort
Style Number/Barcode: 06003-000003
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: RED
Available Size: S, M, L
Product Badge:- Part of a Set