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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Totally Tie Dye Halter Top
This blue top totally has the chill vibes! It features a halter neck with racer bust, a neck tie and cropped hem. The all over tie dye design features gradients of blue and gray hues. Top is composed of a knit fabric that offers a relaxed fit with plenty of stretch.Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1345
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hot Mesh Crop Top
This hot mesh crop top will have you trendy and stylin'! It features a crew neckline, long fitted sleeves, and a cropped hem. The neon purple top is composed of a sheer mesh fabric with plenty of stretch.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-1327
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Knot A Basic Crop Top
Give your crop top a fun twist to add a stylish touch! This white top features a sleeveless bodice, a V neckline with a tie front accent, narrow shoulder straps and a cropped hem. Top is composed of a smooth knit fabric with plenty of stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1290
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Sprung On Spring Bodysuit
Get sprung on spring with this adorable floral bodysuit! It features a sleeveless bodice, spaghetti straps, a plunging V neckline created by a wrap front, pleated detailing, and a thong bottom with snap button closures. The mauve bodysuit is composed of a knit fabric that offers plenty of stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1293
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Can't Relate Henley Mini Dress
Basic? Sorry can't relate. Stand out in this natural mini dress that features a sleeveless bodice, a sweetheart neckline, a multi button down front with wooden buttons, wide shoulder straps and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1279
Category Name: Vacation Looks
Price: $22.00 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smock It Leopard Crop Top
Smock it for a fierce look today! This leopard print top features spaghetti straps, a super stretchy smocked design and a cropped length.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1253
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Scoop Neck Bodysuit
Make your festival 'fit a fierce one with this snake print bodysuit! It has a sleeveless bodice, thin shoulder straps, a scoop neckline, and a thong bottom with snap button closures. The garment is composed of a knit fabric with plenty of form hugging stretch.Model is 5'9" with a 32" bust, 23" waist, and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1215
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love For Bows Strapless Ponte Crop Top
What's not to love about this adorable bow crop top? It boasts a sleek strapless neckline with front bows and a flirty cutout.
Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless neckline
- Front bows, cutout design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000122
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffle Spaghetti Strap Crop Top
Draw some attention in this super cute peach crop top! It features a V neckline, spaghetti straps, a draw string accent that creates a ruched bust area, and a ruffled hemline. Ribbed knit fabric offers plenty of stretch.Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1203
Category Name: Vacation Looks
Price: $15.00 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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It's A Wrap Crop Top
Complete your 'fit with the perfect ivory crop top this season! It's cool, casual, with a trendy twist. It has a plunging V neckline, short sleeves, and a wrap around detail at the hem. Top is composed of a ribbed knit fabric with plenty of stretch.Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1222
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mesh With Me Cover Up
Stir up the scene in this must have mesh cover-up. It features a round neckline, long sleeves, a drawstring side and a mini length. Mesh fabric is sheer and unlined.Model is 5'9" with a 33" bust, a 24" waist, and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-1211
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mesh With The Best Crop Top
You only mess with the best style! This fab crop top features a round neck, long fitted sleeves, and a cropped hem. The bright neon yellow top is composed of a sheer and stretchy mesh fabric with a form hugging style. Bralette not included with garment.
Style Number/Barcode: 06001-0911
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bright And Early Crop Top
Start bright and early with a little hot neon 'fit! The one shoulder top has a wide strap paired with an extreme cropped fit. The crop top has a form fitting fabric composed of a smooth knit that offers a moderate stretch. Don't forget to purchase the matching skirt.Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-0658
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crop Till You Drop Top
When you can't get enough crop tops in your life, add this beauty to your collection! It features a sleeveless bodice, a V neckline with narrow shoulder straps, subtle princess seams and a cropped hemline. Top is composed of a crepe fabric that offers a relaxed fit with a moderate stretch. Garment is lined with a smooth knit fabric.
Style Number/Barcode: 06001-9936
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek And Sultry Midi Dress
Take the plunge in this sexy midi dress to get hearts racing! It features a royal blue hue, a plunging V neckline and narrow shoulder straps. The slim fit bodice leads to a curve hugging midi length silhouette to show off those va-va voom curves. Dress is composed of a crepe knit fabric.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05103-3555
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Next Level Bodycon
Take your look to the next level in this wowing bodycon dress! It features a spring ready lavender color, a square neckline, wide tank-like straps and a midi length skirt with a sexy high slit. Dress is composed of a textured knit fabric that offers a form hugging bodycon fit to showcase curves!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-3486
Category Name: Vacation Looks
Price: $10.00 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get The Ponte Midi Dress
Get your point across in this bold midi dress! This sexy midi features an ivory hue, a plunging V neckline, narrow shoulder straps and an empire waist accent that leads to a curve hugging midi length skirt. Dress is composed of a curve hugging ponte knit fabric that offers a moderate stretch.
Style Number/Barcode: 05103-0022
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Graceful Lace Open Back Midi Dress
Keep it graceful in elegant lace! This white midi dress features a plunging V neckline, narrow shoulder straps and an open back with a scalloped lace trim. Dress is composed of a combination ponte and lace fabric that offers a form hugging fit with a moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05103-0006
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Beauty Button Down Dress
You're such a beauty, and this button down dress will look so perf on you! It features a sleeveless bodice, thin shoulder straps, a square neckline with a front button closure, a square back, a faux button down front, and a short, curve hugging fit. The ivory ribbed knit dress offers plenty of stretch.Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-4046
Category Name: Vacation Looks
Price: $7.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hello Gorgeous Wrap Mini Dress
Hey gorgeous! Flatter those curves in this blush pink wrap mini dress! It features a deep V neckline that wraps and ties at the waist, narrow shoulder straps, and a wrap skirt that creates a tulip hem. Dress offers a comfortable slim fit and is composed of a stretchy, crepe knit fabric.Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-4018
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Brighten Up My Day Mini Dress
Brighten up the day with this pretty yellow mini dress! It features a sleeveless bodice, halter straps with a racer back with a keyhole cut out and a back button closure, seam detailing, and a short, asymmetrical hem. The dress is composed of a crepe fabric that offers moderate stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0023
Category Name: Vacation Looks
Price: $10.00 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Bit Of Sweetness Off-Shoulder Crop Top
This fun and flirty off-shoulder crop top adds a bit of sweetness to your favorite bottoms!
Fit & Features
- Smooth, stretchy knit fabric
- Off-shoulder neckline
- Tie-back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000044
Category Name: Vacation Looks
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twist In Florals Maxi Dress
Give your look a pretty twist in this navy maxi dress! It features a sleeveless bodice, a plunging V neckline, narrow shoulder straps and an open back with tie strap accent. The slim fit bodice leads to a curve hugging maxi length silhouette accented with a high side slit. The all over floral print features pink hues to contrast with the navy background. Dress is composed of a lightweight woven fabric that offers a form hugging fit with a minimal stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05102-4015
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Buttoned And Striped Maxi Dress
Give yourself a cute and casual look with this buttoned and striped maxi dress! It features a sleeveless bodice, spaghetti straps, a scoop neckline, a faux button down front, and a front slit. The black and white dress is composed of a knit fabric with plenty of stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-4028
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free