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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Stay Sassy Tie Front Top
Stay ever so sassy in this stylin' snake print top! It features three quarter length flowy kimono style sleeves, a tie front, and a cropped hem. The top is composed of a sheer chiffon fabric woven with gold sparkly thread and features hues of taupe and mustard yellow.
Model is 5’9” with a 32” bust, 24.5 waist, and 35” hips. She is wearing a size small.
Style Number/Barcode: 06204-0097
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Drippin' In Rhinestones Swim Bottoms
Girl, you'll be drippin' in rhinestones with these fab black swim bottoms! They feature a large rhinestone adorned front band paired with a partial coverage bottom. Complete your look with the matching swim top!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0385
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beat The Heat Cutout Jumpsuit
As temperatures soar, keep your cool in a crisp, linen-blend jumpsuit just like this one. Suit features adjustable spaghetti straps, a knotted tie-front bodice with cutout detail, a smocked back and zip closure, and wide-leg, cropped pants with pockets at either hip. Jumpsuit is made from a lightweight, gauzy material with minimal stretch.Style Number/Barcode: 06302-0055
Category Name: Vacation Looks
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bodycon Bite Dress
Say it with snake—this bodycon style has serious bite. Dress comes in a curve-hugging mini cut and features spaghetti straps and a rounded neckline. Dress is made from a soft brushed knit with a fair amount of stretch.Style Number/Barcode: 05103-0230
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Steal The Scene Skater Dress
Steal the scene and turn heads in this captivating skater dress! It features a sleeveless bodice, spaghetti straps that lead to an open cross back and lattice details, vertical seams that run down the bust, a high waist seam, and a flowy high low skater skirt. The dress is composed of a crepe fabric that offers moderate stretch.Style Number/Barcode: 05101-8832
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Level Up Platform Heels
Elevate your look to the next level in these head turning heels! The heels feature an open back, an adjustable ankle strap, criss-cross straps with a peep toe, a wide platform and a block heel. They are composed of a faux nuck material.
Style Number/Barcode: 07401-0028
Category Name: Vacation Looks
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Magically Iridescent Duffle Bag
Bring a little magic with you with this glimmering multi-colored iridescent duffle bag! It features a top gold zipper opening, large handles, and a sturdy textured body. The woven lined interior includes an open pocket and zippered pocket as well as an included shoulder strap to hook on. The exterior of the bag is composed of a faux leather material.
Style Number/Barcode: 07203-1788
Category Name: Vacation Looks
Price: $17.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mini Cross Pendant Necklace
Add this pretty mini cross pendant necklace to any outfit! It features a dainty and delicate gold colored chain with a mini cross charm. The necklace includes an adjustable lobster clasp closure.
Style Number/Barcode: 07002-4808
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Livin' The Glam Life Earring Pack
Live your best glam life with this radiant gold earring pack! The set features three pairs of earrings, two pairs of tube hoops and one pair of round studs. The earrings include post back closures.
Style Number/Barcode: 07001-4339
Category Name: Vacation Looks
Price: $5.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Good Vibes High Rise Boyfriend Jeans
Bring the good vibes to your casual everyday look with these trendy boyfriend jeans! They feature a high-rise waist, a straight leg, major destructed detailing at the knees, and a relaxed fit. The light wash denim fabric offers minimal stretch. Style these jeans with a cute crop top and clear heels.
Fit & Features
- High-rise waist
- Straight leg
- Destructed detailing at the knees
- Relaxed fit, minimal stretch
- Light wash denim fabric
- Traditional five-pocket and belt loop design
- Hidden zipper and front button closure
- Runs true to size
Style Number/Barcode: 06602-0241
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Step Glitter Sneakers
Put a little sparkle in your step—literally—when you slip into these sneakers! They feature all-over glitter embellishment, classic lace-up styling, a patent shell toe, rubber midsoles and outsoles, and a contrast patent strip at heel.
Style Number/Barcode: 07407-0015
Category Name: Vacation Looks
Price: $14.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Got Me Twisted Anklet Pack
Bring the bling all over! Add some shine with this stretchy anklet set. Each anklet features two strands of rhinestones in an elegant twist design.
Style Number/Barcode: 07003-0013
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glow Up Strappy Sandals
Give your sandal game a glow up in these shine-worthy beauties! The sandals feature an open back, an adjustable ankle strap, a double band strap design with an open toe.
Style Number/Barcode: 07404-0523
Category Name: Vacation Looks
Price: $12.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fierce Double Buckle Sandals
Keep it fierce in this must have sandals! They feature an easy slip on design, a double band accent with adjustable buckles and a wide cork-styled foot bed.Style Number/Barcode: 07404-0093
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Every Day Ear Candy Pack
Ear candy for every day of the week? Yes, please! This sleek pack features seven rhinestone ear cuffs and earrings with post-back closures. Two cuffs, one rhinestone and one simple. Two cuff style earrings, and three stud earrings, two simple and one with a three row rhinestone detailing.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0072
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fun In The Sun Wedges
Catch some rays and have some fun in these cute sunny wedges! They have an open peep toe as well as a strappy twist front top, the ankle strap is adjustable and has a gold buckle closure. These suede-like mustard yellow wedges would add the perfect pop of color to your sunny day attire!Style Number/Barcode: 07406-0036
Category Name: Vacation Looks
Price: $13.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Everything's All Bright Tassel Earrings
Put some brightness in your life! These neon yellow earrings feature a gold metal O-ring with a row of tassels. Earrings have a post back closure.
Style Number/Barcode: 07001-4395
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gemstone Tassel Statement Earrings
You'll for sure make a statement in these stunning gemstone tassel earrings! They feature a round rhinestone encrusted stud attached to a flower shaped piece adorned with faceted gemstones and rhinestones. They lead to a large faceted gemstone surrounded by smaller gemstones and rhinestones, creating a beautiful design. A single tassel hangs off the end of the earrings. These cascading beauties feature post back closures.
Style Number/Barcode: 07001-4211
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cut Out Cutie Flats
Create a cute look in these chic must haves to complete your look ! The white flats feature a peep toe, an asymmetrical side cut out and a faux leather body.Style Number/Barcode: 07407-0013
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cross My Heart Espadrille Sandals
Cross my heart and hope to buy these adorable sandals! Featuring an open toe, as well as an open heel, a criss cross band at the toe, and an adjustable metal pin buckle closure. Sandals have a short woven espadrille heel and a faux leather lining. They are composed of a faux leather material.
Style Number/Barcode: 07401-0313
Category Name: Vacation Looks
Price: $14.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Drop Octagon Earrings
Spice it up! These earrings feature a circular pendant that drops to a larger octagon pendant. They have a post back closure and a trendy vibe that will add a little somethin' to that outfit!
Style Number/Barcode: 07001-0135
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Double Row Rose Charm Anklet
Dainty and feminine. This adorable anklet features two chains and a rose charm. Closes with one lobster clasp closure. Add some style to that little ankle of yours!
Style Number/Barcode: 07003-2384
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Double Tear Drop Tassel Earrings
Create double the appeal in these trendy earrings! They feature a double tiered teardrop outline and vibrant orange hued tassels.
Style Number/Barcode: 07001-4551
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sensational City Girl Strapless Cargo Mini Dress
Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!
Fit & Features
- Cotton-blend woven fabric, minimal stretch
- Strapless straight neckline with belt loop detailing
- Front button closure
- Hidden front zipper closure
- Cargo flap pockets
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5503
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free