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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Such A Hot Mesh Cover Up
Yes girl, you'll bring the heat in this black mesh cover up! It features a sleeveless bodice, tank-like shoulder straps, a high round neckline, a high front slit, and a long flowy length. The cover up is composed of a sheer mesh fabric adorned with multi-faceted rhinestones all over.
Style Number/Barcode: 06003-9887
Category Name: Vacation Looks
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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They'll Be Linen Up Crop Top
This is a white linen crop top that everyone will adore this summer! This crisp and airy piece features a deep V neckline leading to a row of faux buttons, short sleeves, a side zipper closure, a tie front detail at the hem, and a relaxed fit throughout. Top is composed of a woven fabric with no stretch.Model is 5'9" with a 32" bust, 23" waist, and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-9848
Category Name: Vacation Looks
Price: $8.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Tie Front Crop Top
Keep it boho chic in this must have red top! It features a round neckline with a keyhole detail, long wide sleeves with elastic wrists, and a cropped length with a tie front accent. Top is composed of a lightweight woven fabric with no stretch.Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-9820
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Darling Woven Drop-Waist Skater Dress
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace.
Fit & Features
- Woven fabric with lace trim woven lining
- Sweetheart neckline, ruched bust, adjustable tie-front
- Tank straps, lace-up back design
- Back zipper and hook-eye closure
- Asymmetric drop-waist, pleated side panels
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3806
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tied In Pinstripes Crop Top
Get tied in trendy pinstripes to make a stylish look! This cute crop top features a plunging sweetheart neckline, a tie front accent, wide shoulder straps, a cropped hem and a smocked back. The all over blue background is complemented with narrow white pinstripes. Top is composed of a lightweight woven fabric that offers a form hugging fit with a minimal stretch.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-9780
Category Name: Vacation Looks
Price: $19.90
Availability: Out of Stock
Product Badge:- Clearance
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Adore Me Linen Crop Top
Everyone will adore you in this summer chic linen crop top! It features short cuffed sleeves, a V neckline created by a wrap front, a front O-ring tie waist, and a cropped hem. The striped top is composed of a lightweight linen fabric with no stretch and showcases hues of natural, black, blue, gray, and burgundy.
Style Number/Barcode: 06003-9785
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Clearance
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Flower Power Off The Shoulder Top
Showcase major flower power with this adorable floral print top! It features an elastic off the shoulder neckline, long sleeves with cuffed hems, and a relaxed fit with an elastic hem. The blue hued top is composed of a sheer woven fabric with no stretch.Model is 5'7" with a 30" bust, 22" waist and 33" hips. She is wearing a size small.
Style Number/Barcode: 06003-9778
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beach Ready Embroidered Mesh Cover Up
Summer, we're ready for you! This beach ready white cover-up features a V neckline, kimono style sleeves, a waist tie and a mini length. Embroidered mesh is unlined and completely sheer. Swim suit not included.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9777
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fall In Line Crop Top
Stun them all in trendy stripes! This cute crop top feature a combination white with light blue hue, a halter neck with racer bust and an open back with tie back accent. Top is composed of a lined lightweight woven fabric that offers a form hugging fit with a minimal stretch. Be sure to pick up the matching skirt to complete your look!Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-9775
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Your Move Fishnet Crop Top
Make your next trendy move in this crop top! It features a crew neckline, long dolman sleeves, and a cropped hem. The top is composed of a sheer fishnet fabric with minimal stretch and offers a relaxed, oversize fit. Undergarment not included.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9746
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Sleeveless Surplice Top
Step up your look in this stunning essential tank! It features a sleeveless bodice, a surplice wrap V neckline, a narrow cross strap accent and narrow shoulder straps. Top is composed of a lightweight lined woven top that offers a relaxed fit with a minimal stretch.Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0048
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Daisy On My Mind Smocked Top
We've got florals on the mind! Stay pretty in this red crop top that features a straight strapless neckline, a smocked bodice and a cropped hem. The all over daisy floral print features blue and yellow hues to complement the red background. Top offers a form hugging fit with a moderate stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06003-0061
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely In Floral Crop Top
Look oh so lovely in floral with this pretty printed crop top! It features a sleeveless bodice, halter adjustable straps that cross in the back leading to a tie back closure, a sheer crochet inset with a sweetheart neckline, and a cropped hem. The white top is composed of a woven fabric with no stretch. Complete your look with the matching shorts!Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0031
Category Name: Vacation Looks
Price: $7.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flaunt It Floral Crop Top
Flaunt your sweet sense of style in this charming top! It features a sweetheart bust with a tie front accent, a smocked back and an all over floral print. Top is composed of a lightweight woven fabric that offers a relaxed fit with slight stretch. Be sure to pick up the matching skirt.Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0137
Category Name: Vacation Looks
Price: $7.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Caught In Neon Mesh Top
Get caught in this glowing trend! The neon yellow top features a crew neck, short sleeves and a cropped hem. Top is composed of an unlined fishnet mesh fabric that offers a relaxed fit with a moderate stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0087
Category Name: Vacation Looks
Price: $19.90
Availability: Out of Stock
Product Badge:- Clearance
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Darling Ruffle Crochet Bodysuit
This darling white crochet bodysuit has a sexy side to it! It features a sweetheart neckline, narrow shoulder straps with a small ruffle trim, a square back, and a sheer crochet bodice with a lined bust. Bodysuit has a full coverage bottom with snap button closures.
Style Number/Barcode: 06003-0106
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Everyday Essential Bodysuit
This everyday essential needs to be in your closet!
Fit & Features
- Sleeveless bodice
- Tank-like shoulder straps
- Scoop neckline
- Thong bottom with snap button closures
- Ribbed knit fabric with plenty of stretch
Style Number/Barcode: 06002-0052
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Out In The Town Lace-Up Skater Dress
Playful and daring, this skater dress showcases your best self with a lace-up back design and flowy short-length hem.
Fit & Features
- Eyelet fabric
- Scoop neckline
- Adjustable spaghetti straps
- Lace-up back design
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-000013
Category Name: Vacation Looks
Price: $33.90
Availability: Out of Stock
Product Badge:- Ships Free
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I Want it Plunging Bodysuit
You want it, now flaunt it in this chic bodysuit! It features a white hue, a plunging halter neck, a ruched detailing at the center of bodice and a thong bottom with a snap button closure. Bodysuit is composed of a ribbed knit fabric.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1502
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Clearance
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A Little Twist Bodysuit
Give your look a little twist for a fun pop! This white bodysuit features a plunging V neckline with a twisted bodice accent, short sleeves and a contrast bottom. Bodysuit is composed of a ribbed knit fabric that offers a curve hugging fit with a moderate. Includes a thong bottom with snap button closure.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1472
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fab And Fresh Crop Top
You'll be feelin' so fab and fresh in this hot crop top! It features a sleeveless bodice, spaghetti straps, a V neckline, seam detailing, and a cropped hem. Top is composed of a stretchy knit fabric that offers a form hugging fit. Complete your look with the matching maxi skirt!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1475
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stand Out In Stripes Crop Top
Stand out in trendy stripes in this cute black crop top! It features a sleeveless bodice, a V neckline, narrow shoulder straps and a cropped hem. The all over white contrasting stripes are complemented with a black background for a classic vibe! Be sure to pick up the matching shorts to complete your look!Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1431
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hooked On Florals Top
Get sprung on pretty florals! The yellow top features a plunging V neckline, a multi hook-eye closure front and narrow straps. The floral print features marigold and purple hues to complement the yellow background. Top is composed of a ribbed knit fabric.Model is 5'9" with 32" bust, 24" waist and 34.5" waist. She is wearing a size small.
Style Number/Barcode: 06001-1411
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Into You Crochet Trim Crop Top
We're just so into you. This must have mauve top features a plunging wired V neckline, thin adjustable straps, statement crochet trim and a zipper back.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1382
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance