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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Coin Link Bracelet
Girl you are a treasure. Let them know with the way you accessorize!
- Gold chain links
- Egyptian style coin charm
- Adjustable lobster clasp closure
Style Number/Barcode: 07003-0040
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated And Chic Faux Leather Trench
Layer on an elevated and chic style with this faux leather trench. The jacket features a lapel collar, long sleeves, side pockets, a tie-front belt to cinch the waist, and a mid-length, relaxed fit. The smooth faux leather fabric has a moderate stretch. Complete the look with heeled booties.
Fit & Features
- Lapel collar
- Long sleeves
- Side pockets
- Tie-front belt
- Mid-length, relaxed fit
- Lined faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-1062
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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O-Ring Beaded Bag
Bring the bling babe with this gorg beaded evening bag!
- Metal large O-ring handle
- Faceted shining bead embellishments
- Zipper closure
- Satin lining
- Small inner pocket
Style Number/Barcode: 07204-0065
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wavy Brim Wool Hat
Hat game too strong! This wool felt hat features faux leather trim with a cute buckle closure. Pair with your favorite jeans, outerwear and booties for a seasonal glow.Style Number/Barcode: 07302-0101
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Extra Large Rhinestone Hoops
Rise and shine with some glam ambition in these show stopping hoops! These extra large hoops are embellished with mini rhinestones and easily close with an omega closure.
Style Number/Barcode: 07001-4118
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ravishing Ruffles Mini Dress
Keep it lovely in pretty ruffles! This twirl worthy dress is perfect for creating a chic look!
Fit & Features
- Off The Shoulder Neckline
- Tiered Ruffles
- Brushed Knit
- Wide Shorts Lining
- Lined
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 05101-0592
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rainy Days Knit Cozy Slipper Socks
Whether it's a rainy day, or a super chilly night in by the fire, a pair of cozy socks are a must have! Not to mention they make the perfect gift for bff.
- Faux fur lining
- Woven knit design
- Over the ankle fit
- Non-slip grip
- Pom-Pom accents
Style Number/Barcode: 07306-0041
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rainbow Hair Coils Set of 8
Throwback to throw ya hair back! This pack of metallic rainbow pony tail holders make an adorable gift, or even an adorable keep for the girl on the go!
- 8 Pack
- Metallic reflection
- Rainbow colors
- Coiled stretch
Style Number/Barcode: 07006-0106
Category Name: Vacation Looks
Price: $5.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flow On Chiffon Mini Dress
Let the good times flow in this pretty mini dress!
Fits & Features
- Elastic Square Neckline With Self Ties At Center Front
- Unlined, Cuffed Long Sleeves
- Ruffle-Trim At Mini Length Hem
- Smocked Skirt
- Chiffon Composition I Fully Lined
- Form Flattering Fit I Moderate Stretch
Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0448
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tryna' Shine Rhinestone Wedge Mules
Its my time to shine and im trynnnaaa make it happen with a pair of rhinestone wedges with a clear heel okayy!
- Square toe
- Double rhinestone bands
- Open back
- Clear lucite wedge heel
- Faux suede
Style Number/Barcode: 07406-0064
Category Name: Vacation Looks
Price: $30.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marble Water Proof Bluetooth Speaker
Lets get loud! This Bluetooth speaker is splash proof, and compatible with most smart phones, and Bluetooth devices. It includes a micro usb charging cable and a built in lithium battery. It also has a built in mic for hands free calling! Were thinking this would make a great gift but something tells us we would want to keep it for ourselves too!Style Number/Barcode: 07308-0063
Category Name: Vacation Looks
Price: $13.00 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Livin' The Life Square Low Heels
Live the life, and live it in comfort in a low heel of course! Also square toes are in right now, now you know, we got ur back bb.
- Faux suede
- Pin buckle closure at ankle
- Low block heel
- Square toe
Style Number/Barcode: 07401-0434
Category Name: Vacation Looks
Price: $18.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Our Faves Multi Scrunchy Pack
Umm it is all our faves wrapped in one of course! This set of scrunchies features a variety of all of our top textures and prints that we are obsessing over at the moment!
- Set of five
- Leopard print | Tiger print
- Chenille | Sherpa
- Wired burnt orange knit
- Elastic with stretch
Style Number/Barcode: 07006-0061
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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My Vibez Rhinestone Choker Necklace Set
We know its your vibe to match your hoops to your choker, because its our vibe too bb! And. We. Love. It.
- Choker + large hoop earring set
- Multi-colored rhinestones
- Hoops have omega closure
- Necklace has adjustable lobster clasp closure
Style Number/Barcode: 07002-0254
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ready For This Jelly Purse
I don't think ya'll are ready for this jelly purse! It is a quilted style with metal hardware and a turn lock closure. The purse has an inner divider as well as a long cross body chain strap. with a rectangular shape and a firm texture this purse is bound to be your new go-to accessory!
Style Number/Barcode: 07203-0058
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tiny & Textured Shimmer Hoops
These hoop earrings have a hint of shimmer to them and are the perfect detail to complete your look. They feature a dainty textured design that is unique from your typical hoop earrings. A great accessory for girl's night, pair these hoops with a crop top and faux leather mini skirt for an edgy vibe.
Fit & Features
- Thin textured design
- Slight shimmer
- Hook and loop closure, post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-0116
Category Name: Vacation Looks
Price: $6.90
Availability: Out of Stock
Product Badge:- Ships Free
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Triple Threat Choker Set
Add an irresistible finish to your outfit with a triple threat design!
- Set of three necklaces
- Lobster clasp closure
- Chokers + single charm necklace
Style Number/Barcode: 07002-4714
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dainty Cubic Zirconia Drop Necklace
Add a dainty detail to your fit with a necklace! This necklace features a dainty chain adorned with rhinestones and a cubic zirconia drop design.
Style Number/Barcode: 07002-0020
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mini Matte Snake Textured Purse
Mini purses, they hold the essentials, and also our hearts because they are so darn cute!
- Mini rectangle structure
- Matching handle
- Matte faux leather
- Snake texture
- Detachable matching shoulder strap
- Snap closure
Style Number/Barcode: 07203-0163
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready For The Weekend Layered Necklace
It's a fun filled weekend, and you won't forget to accessorize will you? The smallest touch of glam make the biggest difference!
- Double Layer Dainty Chain
- Horizontal & Vertical Rhinestone Bars
- Lobster clasp closure
Style Number/Barcode: 07002-0196
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruffle Up Chiffon Off Shoulder Mini Dress
Make every walkway your runway in the Ruffle Up Off Shoulder mini dress!
Fits & Features
- Elastic Off Shoulder Neckline
- Long Sleeves
- Ruffle-Trim At Cuffs, Neckline, Waist, And Hem
- Smocked Skirt And Cuffs
- Mini Length Silhouette
- Chiffon Composition
- Form Flattering Fit I Moderate Stretch
Style Number/Barcode: 05102-0506
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Super Destructed Skinny Jeans
With their trendy destructed detailing and flattering high waist, these skinny jeans need to be in your closet ASAP!
Fit & Features
- High rise waist
- Traditional five belt loop design
- Faux front pockets | Two back pockets
- Front hidden zipper and button closure
- Major distressed detailing
- Skinny leg fit
- Denim fabric | Moderate stretch
Style Number/Barcode: 06602-0052
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Out With The Girls Chain Link Mini Purse
We are talking a weekend out with the girls! A time to dress up, take pics, and drink mimosas, right!?
- Rectangular structured shape
- Gold chain link handle
- Detachable shoulder strap
- Faux leather
Style Number/Barcode: 07203-0164
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Tie Front Blouse
We can't get enough of leopard print! This trendy blouse is perfect for winter with its cooler, neutral tones.
Fit & Features
- Long roomy sleeves with elastic cinched cuffs
- Deep V neckline
- Tie front
- Cropped
- Leopard print
- Cotton woven fabric | No stretch
Style Number/Barcode: 06204-0294
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance