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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Sleek And Sparkle 24 Rings Pack
The more, the merrier, with this pack of 24 rings that give off sleek and sparkle vibes! The set includes 24 bands of both classic sleek rings and rhinestone encrusted rings. The pack includes regular and midi sized bands so they can be stylishly stacked.
Style Number/Barcode: 07004-0960
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hustlin' Rhinestone Frame Sunglasses
There's many ways show you are a hustler, and it starts with a pair of bomb af pair of rhinestone sunglasses!
- Straight brow bar
- Rhinestone frame
- Dainty arms with rhinestone detail
- Cut out center
- 100% UV protection
Style Number/Barcode: 07008-0684
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Danya Scuba Floral A-Line Dress
Special Occasion
Sway and sashay your way around the dance floor with our beautiful Danya! Her delicate floral prints add a flirty feminine touch.
Fits & Features
- Spaghetti Straps
- Plunging V Neckline I Princess Seams
- Zipper With Hook & Eye Closure At The Back
- A-Line, Floor Length Hem I High Slit At The Front
- Smooth Scuba Knit Fabric With Floral Prints Throughout
- Form-Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0355
Category Name: Vacation Looks
Price: $19.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hammered Heart Faux Leather Belt
We know the way to your heart is a statement belt girrrl! Dress up that denim, or even your go-to mini skirt with this simple yet still makes a statement belt!
- Large hammered heart accent
- Ball point buckle closure
- Faux leather
- Belt loop
Style Number/Barcode: 07301-0098
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Holographic Trim Clear Mini Purse
You always roll up with the best purse in hand! And you ain't stoppin' now!
- Holographic Trim Mini Purse
- Clear design
- Silver turn lock closure
- Chain holographic shoulder strap
- Rectangular structure
Style Number/Barcode: 07203-0185
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Ready Faux Wool Panama Hat
Be ready to channel your inner boho with this picture worthy panama hat that we are loving right now! Pair with a simple tee & jeans for an effortlessly trendy vibe!
- Faux wool
- Braided matching belt
- Medium brim
Style Number/Barcode: 07302-0126
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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I'm Busy Cat Eye Sunglasses
Sometimes ur too busy. Sometimes you need to just throw on some shades and go, and we are feelin' this sassy pair for you babe!
- Skinny frames
- Cat eye design
- Dark shading
- 100% UV Protection
Style Number/Barcode: 07008-0682
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Moment Bow Block Heels
These playful floral block heels are giving garden party glam with a cute bow—perfect for twirls, toasts, and turning heads at your next event!
Fit & Features
- Block heel
- Square toe
- Wide strap with bow
- Adjustable ankle strap with buckle closure
- Floral print
- Faux leather padded insole
- Runs true to size
Style Number/Barcode: 07401-000362
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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H8 On This Rimless Rhinestone Sunglasses
Try and h8 on me, you can't. You're too busy wondering where these fire shades came from!
- Brow bar design
- Rhinestone detailing
- Rimless Lenses
- Nose pads
- Light shade
- Solid arms
- 100% UV Protection
Style Number/Barcode: 07008-0683
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Gemstone Statement Necklace Set
Make a statement with a beautiful floral gemstone necklace, composed of the most stunning fuchsia tone that compliments all skin tones!
- Large gemstone design
- Leafy style detailing
- Matching earrings
Style Number/Barcode: 07002-0285
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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It's A Vibe Chain Necklace Set
Layer up with gold chains girl, it's a vibe!
- Set of two necklaces
- Gold chain design
- Pendant accent
- Lobster clasp closure
Style Number/Barcode: 07002-0279
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babygirl Layered Necklace Set
We know you love to layer as much as we do babygirl! An array of multi- layered necklaces can bring life to the simplest outfits!
- Set of five separate necklaces
- Various lengths
- Variety of charms: Heart | Coin | Babygirl script
- Lobster clasp closures
Style Number/Barcode: 07002-0270
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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You Are Stunning Floral Tassel Earrings
You are already stunning, why not highlight your beauty with a little something sparkly!
- Intricate floral post design
- Rhinestone detailing
- Drop tassel fringe
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0244
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 Pearl Door Knocker Earrings
Baby all you need is a small finishing touch and these cutie little pearl door knockers are just the thing!
- Square design
- Pearl detailing
- Post back closure
Style Number/Barcode: 07001-0298
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Layered Pendant Necklace
When you're looking to finish your sleek look the finishing touch is a simple layered gold necklace of course!
- Single necklace | Two layers
- Drop bar pendant
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0256
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Picture Purrfect Mini Skirt
You'll look picture purrfect in this trendy spotted mini skirt babe! Pair with the matching crop top for an on point look.
Shop Matching Top: Picture Purrfect Crop Top
Fit & Features
- High rise waist
- Stretchy smocked back
- Animal print | Woven fabric
- Short, curve hugging fit
Style Number/Barcode: 06401-0161
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Picture Purrfect Crop Top
You'll look picture purrfect in this trendy spotted crop top babe! Pair with the matching mini skirt for an on point look.
Shop Matching Skirt: Picture Purrfect Mini Skirt
Fit & Features
- Off the shoulder sweetheart neckline
- Short puffed sleeves
- Tie front with keyhole cut out
- Stretchy smocked back
- Ruffle trim | Cropped
- Animal print | Woven fabric
Style Number/Barcode: 06003-0622
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Off the shoulder sweetheart neckline
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Skinny Double O-Ring Belt
Whether you're adding a little touch to a flowy dress, or amping up your denim with a skinny belt, you are making the right moves bb!
- Skinny design
- Double O-ring buckle
- Adjustable closures
Style Number/Barcode: 07301-0101
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babes Day Out Panama Hat
It's babes day out, grab your gals and go on an adventure in the city! Don't forget to throw on a panama hat to finish off that look!
- Faux wool
- Curved top
- Braided belt accent
Style Number/Barcode: 07302-0127
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam AF Hair Clip Set
Whether you cut your bangs too short or ur feelin' a like a lil' extra dose of glam, this set of hair clips will get ur look glammed the eff out!
- Set of two
- Large over-sized design
- Rectangular structure
- Snap closure
Style Number/Barcode: 07006-0097
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cubic Zirconia Butterfly Ring Set
That style has our hearts fluttering girrrl! Finish your look the right way with a set of simply dainty butterfly rings!
- Set of five rings
- Three butterflies | Two sleek finish
- Closed design
- Larger rings: size 7
- Midi rings: size 4
Style Number/Barcode: 07004-0049
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Smooth Moves PU High-Rise Shorts
Oh-so-contemporary and sleek, these smooth faux leather shorts feature a high-rise waist, front snap-button, hidden zipper closure, side pockets, seam detailing, and a fitted cheeky hem. The lined faux leather fabric has minimal stretch. Complete the look in a basic tee and boots for an edgy vibe.
Fit & Features
- High-rise waist
- Front snap-button and hidden zipper closure
- Side pockets
- Seam detailing
- Fitted, cheeky hem
- Faux leather lined fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0241
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XS
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Sleek Faux Leather Corset Belt
Level up your look with a corset belt! Designed to fit perfectly below the cups, with a stretchy elastic backing and four metal snap button closures. Belt is thick and composed of faux leather.Style Number/Barcode: 07301-0107
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Justina Floral Velvet Burnout Chiffon Dress
Special Occasion
Get swept away in this dreamy floral dress!
Fits & Features
- Plunging V Neckline I Empire Waist
- Adjustable Spaghetti Straps That Cross At The Back
- Zipper With Hook & Eye Closure At Back
- A-Line, Floor Length, Flowy Fit Skirt
- Chiffon Fabric With Velvet Burnout Floral Detailing I Fully Lined
- Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0452
Category Name: Vacation Looks
Price: $9.97 $124.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free