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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Butterfly Bombshell Hoop + Stud Set
You are a bombshell babe! Highlight ur look with a sweet set of studs and hoops! Wear alone or layer them up!
- Set of 9 earrings
- Mixed metals: Silver | Rose Gold | Yellow Gold
- Rhinestone, pearls, studs, hoops
- Post back closure for studs
- Omega closure for hoops
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0255
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leopard Trim Clear Mini Purse
Introduce a little leopard print into your wardrobe babe! This clear purse is a subtle way to add a trendy touch to your look!
- Rectangular structure
- Clear design
- Leopard print trim + Turn lock closure
- Gold link chain shoulder strap
Style Number/Barcode: 07203-0172
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Dayz Beaded Bracelet Set
Get ur boho vibes going with layers of beaded bracelets! The different designs bring an effortlessly chill vibe to ur loook!
- Set of seven bracelets
- Stretchable
- Gold | Pink | Ivory
- Iridescent finish
Style Number/Barcode: 07003-0062
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wifey Material Bra + Panty Set
Girl you are wifeyyy material, let him know when you dress yourself up in this classy lace bra + panty set!
Fit & Features
- Two piece
- Corset style wired lace bra with padding
- Three hook and eye adjustable closures
- Adjustable straps
- Matching lace panties
- Thong bottom | Moderate stretch
- Sheer front with lace detailing
Style Number/Barcode: 07107-0369
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Rise Clean Skinny Jeans
Lusting after the perfect pair of high rise skinny jeans? Look no further and add these to your cart. You'll thank us later.
Fit & Features
- High rise waist
- Traditional five pocket and belt loop design
- Front button and hidden zipper closure
- Clean design
- Skinny leg fit
- Denim fabric | Moderate stretch
- Form hugging fit
Style Number/Barcode: 06602-0076
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Floral Tie Front Top
Satin is the fabric of the season, and the romantic floral print adds a pretty touch to this tie front top.
Fit & Features
- Long sleeves | Elastic banded cuffs
- Tie font detail | V neckline
- Cropped
- Satin-like fabric | No stretch
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0315
Category Name: Vacation Looks
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lead The Way Rhinestone Clear Flats
For the babe that is ready to lead to way, the boss babe that is always on the go, and the always working lady, you don't have to wear heels to make a fashion statement!
- Pointed toe
- Clear design
- Ankle strap
- Rhinestone detailing
- Pin buckle closure
Style Number/Barcode: 07405-0015
Category Name: Vacation Looks
Price: $14.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bella Super High Rise Destructed Jeans
Oasis by Eunina
Bring the edge with these daring skinny jeans!
Fit & Features
- Super High Rise Waist
- Single Button | Zipper Closure
- Traditional Five Pocket Design
- Heavy Destruction
- Skinny Leg Fit
- Raw Edge Hem
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 06602-0047
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Glam Rhinestone Hoop Earrings
Create a soft glam look with a pair of stunning rhinestone hoop earrings, bound to dress up that cute messy bun of yours!
- Large hoop design
- Three row rhinestone embellishments
- Omega closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0242
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Check You Out Square Toe Heels
Check you out bb, you are having a moment in those square toe heels!
- Square open toe
- Thong strap toe
- Strappy wrap lace closure
- Skinny high heel
- Faux suede
Style Number/Barcode: 07401-0759
Category Name: Vacation Looks
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double O-Ring Rhinestone Belt
Add double the glam to your look with an all over rhinestone belt!
- Faux leather
- Double O-ring ball snap closure
- Rhinestone detailing
- Skinny design
Style Number/Barcode: 07301-0097
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Silicone Adhesive Lifting Bra
This lifting sticky bra with adjustable lace-up detail provides the perfect support and lift for any open-back or strapless style. The sticky push-up bra is made of a smooth gel with a skin-like appearance and has an adjustable lace-up design to give you a customizable fit.
Fit & Features
- Soft, seamless padding
- Lined with a strong adhesive to stay in place all day
- Lace-up system
- Can be worn up to 25 times
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: 07101-0209
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: NATURAL
Available Size: A, B, C, D
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Clearly Busy Point Toe Flats
Even tho you are clearly movin' up in the world, making moves, and living your best life, you still make time to make sure ur shoe game is on point!
- Closed pointed toe
- Clear design
- Ankle band
- Clear sling back
- Pin buckle closure
- Flat sole
Style Number/Barcode: 07405-0017
Category Name: Vacation Looks
Price: $14.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slidin' In Ur Dm's Snake Textured Slides
Your comfy laid back lewk will have them slidin' in ur dm's baybayyy!!
- Open round toe
- Metallic finish
- Snake textured band
- Short platform sole
Style Number/Barcode: 07404-0099
Category Name: Vacation Looks
Price: $10.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On My Basic Ish Strappy Sandals
Sometimes you gotta stay on your basic ish and have a staple pair of strappy sandals! You never know when you'll be on your next vacay, walkin' on the beach!
- Almond toe
- Slanted strap detail
- Pin buckle closure
- Flat sole
Style Number/Barcode: 07404-0097
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Simple Dainty Bracelet Set
Add some sweet simplicity to your look with a set of dainty bracelets!
- Set of four separate bracelets
- Dainty design
- Variety of accents
- Lobster clasp closure
Style Number/Barcode: 07003-0047
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrapped In Gorgeous Floral Blouse
Get all wrapped up in gorgeous florals with this lightweight blouse!
Fit & Features
- Surplice front design | V neckline
- Long puffed sleeves with elastic banded cuffs
- High waist seam
- Partial open back | Tie closure
- Sheer chiffon fabric | No stretch
Style Number/Barcode: 06003-0334
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Mesh Surplice Bodysuit
Tis the holiday season with a major floral moment! This wrap front bodysuit has a stunning burgundy hue and all over floral print, pefect for your celebratory parties!
Fit & Features
- Long sheer sleeves with elastic banded cuffs
- Surplice front design | Plunging V neckline
- Knit thong bottom | Dual snap button closures
- Mesh fabric | Partial knit lining
- Moderate stretch
Style Number/Barcode: 06003-0425
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blinged Out Rhinestone Wireless Headphone Case
We know you bb, blinged out everything all day!
- Wireless headphone case
- Multi-colored rhinestones
- Precise cut-outs to the charging port and pairing button
- Headphones not included
Style Number/Barcode: 07308-0055
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Please Girl Point Toe Wedge Heels
Please girl, go on with your bad self! These point toe heels give you a little edge, and we are a fan!
- Open pointed toe
- Single band
- Ankle strap w/ pin buckle closure
- Wedge heel
- Natural wedges are shiny patent
- Black wedges are faux suede
Style Number/Barcode: 07406-0058
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Cat Leopard Off Shoulder Mini Dress
Leopard prints FTW. You'll be having a moment everywhere you go in the Cool Cat off shoulder mini dress!
Fits & Features
- Smocked Off Shoulder Neckline
- Roomy Cuffed Long Sleeves
- Elastic, Smocked Skirt
- Subtly Pleated, Mini-Length Hemline
- Form-Hugging Fit WIth Plenty Of Stretch
Style Number/Barcode: 05102-0397
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Skinny Rhinestone Belt
Bling it on! This trendy dainty skinny rhinestone belt will cinch your look and snatch that waist babe!
- Adjustable embellished square buckle closure
- Seven rows of rhinestones
Style Number/Barcode: 07301-0102
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crochet Fringe Shawl
Keep it timelessly elegant with a this luxe inspired shawl! It features a metallic crochet design and a fringed hem. Shawl is composed of a lightweight crochet knit fabric.Style Number/Barcode: 07305-0007
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Belted Boater Hat
Add this essential hat to complete your looks! It features a traditional boater design and belt accent to adorn the rim. Hat is composed of a faux wool material.Style Number/Barcode: 07302-0008
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale