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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Fab In Florals Maxi Dress
Keep it fab and gorgeous in florals! This pretty maxi dress features a navy blue color, a sleeveless bodice, a V neckline and narrow shoulder straps. The back features an open back design with a tie back accent. The slim fit bodice leads to an elongating maxi length. The all over floral print features vibrant hues for a fresh look! Dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Includes a mini skirt length knit lining.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-4016
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Cutie Linen Maxi Dress
Go for casual and cute in this taupe dress! It features a V neckline, adjustable narrow straps and a maxi length silhouette with hidden side pockets. Dress is composed of a double lined linen knit fabric that offers a relaxed fit with minimal stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3966
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plus Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining.
Style Number/Barcode: 15102-0017
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blooming Beauty Mini Dress
Have a cute brunch with your bffs as you bloom with beauty in this floral mini dress! It features an off the shoulder neckline with an overlay, a high waist seam, and a subtle ruffled seam at the hem. The black dress is composed of an unlined lightweight, flowy linen fabric with no stretch and showcases a pretty pink floral print.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-3981
Category Name: Vacation Looks
Price: $10.00 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovely Little Floral Dress
Look oh so lovely in this little floral printed mini dress! It features a sleeveless bodice, spaghetti straps, a square neckline, a lettuce edge trim, and a short, form hugging fit. The natural hued dress is composed of a smocked and stretchy linen fabric and showcases an adorable all over ditsy floral print.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3979
Category Name: Vacation Looks
Price: $13.94 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Back In Basics Mini Dress
Fall back on basics for an effortlessly trendy look! This ivory mini dress features a sleeveless strapless bodice, a square neckline, and a short, curve hugging fit. The basic dress is composed of a sheer knit fabric with a full knit lining and offers 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: 05102-3971
Category Name: Vacation Looks
Price: $10.00 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Artist's Muse Chiffon Maxi Dress
Steal the show in this bold, abstract-print maxi dress. Dress features a deep V neckline, side cutouts, a spaghetti strap crisscross back with tie, and a full, gently pleated skirt with front slits. Dress is made from a lightweight, chiffon-like material and has moderate stretch at the back waist.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3953
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim For Days Mini Dress
We're living for denim this season! Slay any day in this cute denim dress that features a scoop neckline, adjustable narrow straps and a matching scoop back. The curve hugging mini length silhouette features faded accents to create a pretty contrast! Dress is composed of a double lined denim fabric that offers a moderate stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 05102-3952
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casually Chic Maxi Dress
This black maxi dress is the perfect base piece to dress up or down for a casually chic look! Dress features a scoop neckline, adjustable spaghetti straps, and a comfortable slim fit. Dress includes a full lining and is composed of a soft, lightweight knit fabric that offers a moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3931
Category Name: Vacation Looks
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blossom In Florals Maxi Dress
Let your natural beauty shine through in this pretty maxi dress! It features a taupe hue, a sleeveless bodice, a plunging V neckline, narrow straps that cross at the back and a maxi length skirt with a high side slit. The all over floral print features blue with pink hues that are complemented with a green foliage.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05102-3930
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cute As A Button Mini Dress
You'll look cute as a button in this pretty mini dress! The dress features a blue hue, a sleeveless bodice, a square neckline, adjustable narrow shoulder straps, a button down side seam and a mini length silhouette. Dress is composed of a linen fabric that offers a form hugging fit with 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: 05102-3921
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Much Personality Strappy Block Heels
Give your outfits some cuteness in these strappy block heels, perfect for pairing with your favorite bottoms or dresses!
Fit & Features
- 3" Round block heel
- Square toe
- Strappy design
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000087
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Button Knit Up Mini Dress
Button up in this adorable mini navy blue dress! It features a sleeveless bodice, spaghetti straps, a scoop neckline, a faux button down front, and a short, fitted look. The dress is composed of a ribbed knit fabric that offers plenty of stretch and a curve hugging style.
Style Number/Barcode: 05102-3915
Category Name: Vacation Looks
Price: $10.00 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Walk The Line Skater Dress
Step out and line it out in stripes! This pretty light blue dress features a plunging V neckline, tank-like straps, a cinching tie waist accent and a flaring skater skirt. The all over striped design is all you need for the perfect spring time look! Dress is composed of a linen fabric with a knit lining.Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-3843
Category Name: Vacation Looks
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Striped In Style Skater Dress
Stay styling in stripes in this cute mini dress! It features a pretty blue hue, a sleeveless bodice, a V neckline, adjustable narrow straps and a wide waistband accent that leads to a flared skater skirt. The back features an open design and is accented with a cute tie-back detail. The narrow white stripes provide a beautiful contrast for the blue background. Dress is composed of a lightweight woven fabric that offers a form hugging fit with a minimal stretch. Includes a lower back zipper closure.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-3888
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Paradise Maxi Dress
Transport yourself to the tropics in this pretty paradise ready maxi! The pink dress features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, a high waist seam, and a flowy maxi length with a sultry front slit. The dress is composed of a knit fabric with moderate stretch and a perfect all over floral and palm print.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-3886
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bohemian Feels Maxi Dress
Get those boho vibes going in this summer ready maxi dress! It features an ivory hue, a sleeveless bodice, a plunging V neckline, sexy waist cut outs and narrow adjustable straps that lead to an open back design. The back features a smocked elastic band and a tie back accent. The waist leads to a sweeping maxi length silhouette accented with a high side slit. The navy blue bohemian design is perfectly complemented with the ivory background. Dress is composed of lightweight woven fabric that offers a relaxed fit with 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: 05102-3878
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced In Floral Maxi Dress
Lace yourself up in pretty florals! This blue maxi dress features a sleeveless bodice, a plunging V neckline and narrow straps that lead to an open back with lattice design. The relaxed fit bodice leads to a curve hugging maxi length silhouette. The all over rose print features white and pink hues for a perfectly spring look! Dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 05102-3873
Category Name: Vacation Looks
Price: $10.00 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Babe In Crochet Skater Dress
This babe is ready for summer in this flirty blue crochet dress! It features a crochet bodice with a plunging V neckline, adjustable shoulder straps that lead to a cute tie back detail, and a flattering wide empire waist panel that leads to a flowy gauze skirt. Includes a knit lining.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-3842
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spring Stunner Maxi Dress
Lace up in this pretty dress for those spring time vibes! It features a white hue, a sleeveless bodice, a V neckline, adjustable narrow straps, a tie back accent and a lower back keyhole. The waist features an unlined crochet floral detail and leads to a sweeping maxi floor length skirt. Dress is composed of a combination crochet and linen fabric that offers a form hugging fit with minimal stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0052
Category Name: Vacation Looks
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantically Crochet Maxi Dress
Revel in romance this summer in this flowy purple maxi dress! It has a plunging neckline, narrow shoulder straps that lead to an open back paired with crochet panels, a gathered bust, a sheer crochet waist, and a flowy floor length skirt with a short lining. Includes a hidden back zipper closure.Model is 5'8 with a 32" bust, 23" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3835
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely Little Linen Dress
You'll look like a total beauty in this lovely little linen dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a wrap front, a side tie detail, a back zipper and hook and eye closure, and a wrap skater skirt with a faux button down front. The olive green dress is composed of a linen fabric with a short linen lining and offers a flowy fit.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-3831
Category Name: Vacation Looks
Price: $10.00 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beautifully Buttoned Skater Dress
Beautifully button up your look with this adorable olive green skater dress! It features flowy short sleeves, a plunging V neckline, a high waistband, an open back with a tie closure with tassel details, a tie back accent, a hidden back zipper and hook and eye closure, and faux buttoned detailing. The dress is composed of a woven gauze fabric with a short lining, pretty pleats, and a flirty, flowy fit.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: 05102-3748
Category Name: Vacation Looks
Price: $10.00 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral To The Maxi Dress
This gorgeous printed maxi dress is floral to the max! It features an off the shoulder neckline, short flutter sleeves, a square neckline, a stretchy smocked top, a tie front waist, and a high low wrap front. The mauve dress is composed of a woven fabric with a flowy fit.Model is 5'8" with a 32" bust, 24.5" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3742
Category Name: Vacation Looks
Price: $17.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free