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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Tropical Getaway Bodysuit
Getaway to a tropical paradise in this gorgeous printed bodysuit! It features a sleeveless bodice, thin shoulder straps, a plunging V neckline, an open back, and a partially covered bottom. The olive green bodysuit is composed of a mesh fabric that offers a form-fitting style with moderate stretch. Complete your tropical look with the matching duster!Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1488
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Miami Muse Watercolor Bodysuit
Bold shades of ocean blue, cobalt, navy, and turquoise lend this vibrant one piece its eye-catching appeal. Bodysuit features an all-over abstract print, tie-neck, halter-style deep V bodice, open back, and cheeky bottoms. Pair it with the matching duster for maximum impact! Garment is made from a smooth, stretchy material.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1235
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Earn Your Stripes Bodysuit
Not just for your favorite tee, stripes add a touch of classic chic to this bodysuit. Suit features all-over ribbing, underwire cups at bust, snap-button closure, and adjustable spaghetti straps at shoulders and back. Suit is made from a soft knit material with moderate stretch.Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1563
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Between The Lines Striped Bodysuit
Get hyped on stripes in this perfectly flirty, multi-color ribbed bodysuit. Pair it with cutoffs and you're good to go! Suit features a ruffle-trim, deep V neckline with ladder cutout detail, a thong-style bottom, and snap-button closure. Suit is made from a soft, woven material with just a hint of stretch.Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1555
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cassandra Floral Chiffon Gown
Special OccasionTake our breathe away in our beautiful mauve toned Cassandra Floral Gown! She features a cross over V neckline and ruffle spaghetti straps that are adjustable. The v style back line has matching material buttons and a hook closure. Long, floor-length skirt offers a flowy fit and includes a short skirt lining. Dress is composed of a semi-sheer floral chiffon fabric with no stretch.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6741
Category Name: Vacation Looks
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sparks Ignite Heat Stone Tunic
Sparks will ignite when you style up this sultry heat stone embellished tunic! It features a sleeveless bodice, a scoop neckline, thin shoulder straps, and a form hugging fit that hits around the knees. The sheer tunic is composed of a stretchy mesh fabric embroidered with gorg dazzling heat stones.Model is 5'9" with a 32" bust, a 24.5" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0128
Category Name: Vacation Looks
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet And Sheer Lace Kimono
Make your look clearly sweet and stylish with this sheer lace kimono! It features short kimono style sleeves with a lace scalloped detail, a tie front closure, and a mid-length, flowy relaxed fit. The crochet lace kimono has no stretch.Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0069
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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More Glow Lace Bustier
Need more glow? Add this bustier top to your 'fit! It features a sleeveless bodice, a flattering underwire, sweetheart bust, adjustable spaghetti straps, a back hook and eye closure, and a pretty eyelash trim detail. The top is composed of a sheer lace fabric with a form-fitting style.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0093
Category Name: Vacation Looks
Price: $8.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flowy In Floral Maxi Dress
Create a flirty and flowy look with this gorgeous floral maxi dress! It has a sleeveless bodice, a strapless square neckline, a stretchy, smocked knit top, and a sheer chiffon high low maxi skirt with a front side slit and a short knit lining. The dress showcases an all over floral print.
Style Number/Barcode: 05102-0037
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Instant Fave Faux Suede Platform Sneakers
A pair of faux suede sneakers feature a round toe, rubber gum platform sole that elevates the look, a lace-up front, and a side striped design. Perfect for everyday styling.
Fit & Features
- Faux suede material
- Round toe
- Rubber gum platform sole
- Lace-up front
- Side striped design
- Runs true to size
Style Number/Barcode: 07407-0232
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Romantic High Waist Pants
Show your sweet, romantic side in these adorable high waist pants! They feature a high rise fit, an elastic banded waist, and straight pant legs with a flared hem. The pants are composed of a crepe fabric that offers moderate stretch and a form hugging style. Complete your romantic look with the matching crop top!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06502-0018
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Studded And Stylin Sandals
Step out in these stylin sandals! They feature an adjustable sling back strap, a multi strap design with an open toe. Straps are embellished with studded details.
Style Number/Barcode: 07404-0030
Category Name: Vacation Looks
Price: $13.97 $17.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bling On The Glam Sandals
Bring on the glamour with these beautiful embellished sandals! They feature an open back, an adjustable ankle strap, a gold sparkle thong strap design adorned with leaf shaped rhinestones, and a flat brown faux leather sole.
Style Number/Barcode: 07404-0018
Category Name: Vacation Looks
Price: $12.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Layered In Lace Skater Dress
Layer up in lace for a charming look! This dress features a plunging V neckline with a scalloped lace trim, adjustable narrow straps that lead to a cross back design and a floral lace bodice. The flared skater skirt features a double layer design to create a head turning moment. Dress is composed of a lined crepe fabric that offers a form hugging fit with a moderate stretch.Style Number/Barcode: 05101-8796
Category Name: Vacation Looks
Price: $9.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lace Stunner Layered Skater Dress
Stun in lace as you make a gorgeous impression! The dress features a sleeveless bodice, a V neckline, a lined floral lace bodice and adjustable narrow cross straps. The slim fit bodice leads to a double layered skater skirt. Dress is composed of a lined chiffon fabric that offers a form hugging fit with a minimal stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-8745
Category Name: Vacation Looks
Price: $15.00 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flower Power Chiffon Maxi Dress
Power through the day with gorgeous florals! This navy blue maxi dress features a sleeveless bodice, a V neckline with narrow straps, princess seams and a waistband accent. The back features an unlined floral lace accent with an open lower back. The slim fit bodice leads to a flowing carefree maxi length. The all over navy blue hue is accented with a teal hued floral design. Dress is composed of a slightly sheer chiffon fabric that offers a relaxed fit with minimal stretch. Includes thin knit lining.Model is 5'7" with a 32.5" bust, 22.5" waist and 34.5 hips. She is wearing a size small.
Style Number/Barcode: 05101-0019
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slay In Crochet Sweater Dress
Slay all day in gorgeous crochet with this sweater dress! It features a sleeveless bodice, thin tie shoulder straps, a round neckline, a faux button down front, and a short, form hugging fit. The dress is composed of a sheer crochet fabric with a sheer waist inset and a knit lined top and bottom.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0025
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus Flowy Floral Maxi Dress
Spring into gorgeous florals in this sweetly inspired maxi dress! It features an off the shoulder neckline, a smocked bodice, short sleeves and a wrapped maxi silhouette. The all over floral print features pretty flowers throughout with foliage. Dress is composed of an hued slightly sheer woven fabric that offers a relaxed fit with minimal stretch. Includes a mini skirt length knit lining.Model is 5'9" with a 44" bust, 37" waist and 47" hips. She is wearing a size 1X
Style Number/Barcode: 15102-0022
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus The Floral Treatment Dress
Give yourself the floral treatment in this darling dress! It features a sleeveless bodice with a square neckline, narrow shoulder straps leading to a square back, a subtle yet flattering empire waist seam, and a body-hugging fit throughout. Dress is composed of a thick, scuba knit fabric with a moderate stretch.Model is 5'11 with a 38" bust, 37" waist, and 48.5" hips. She is wearing a size 1X.
Style Number/Barcode: 15101-0078
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Low Wedge Ankle Strap Sandals
Keep it simple but always cute! These black sandals feature a single strap, open toe design, a closed back with an adjustable ankle strap and a back zipper, and a low wedge heel. The shoes are composed of a faux suede fabric.
Style Number/Barcode: 07406-0210
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Step Up Espadrille Wedges
Step up your sandal game with these super cute black and tan espadrille wedges. They feature an open toe, ankle strap with buckle, and a platform wedge heel.
Style Number/Barcode: 07406-0031
Category Name: Vacation Looks
Price: $22.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Classic Short Wedge Sandal
Keep it simple but always cute! These white dressy sandals feature a single strap, open toe design, a closed back with an ankle strap and a back zipper, and a low wedge heel. The shoes are composed of a faux leather material.
Style Number/Barcode: 07406-0029
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wide Fit Strap Wedge Sandals
Keep it comfy and cute with these Wide Fit Wedge Sandals. They come in a natural color and feature an open toe single strap design, a cross strap ankle with buckle, extra soft padding and a wedge heel.
Style Number/Barcode: 07406-0003
Category Name: Vacation Looks
Price: $16.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Confident Cutie Sleeveless V-Neck A-Line Mini Dress
Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!
Fit & Features
- Soft and stretchy rib knit fabric, full knit lining
- V-neckline
- Spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5651
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free