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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Floral Fusion Midi Dress
Infuse your spring looks with pretty florals! This midi dress features a sleeveless bodice, a V neckline and narrow cross straps. Dress is composed of a smooth slate hued knit fabric adorned with a multi hued floral print. Garment 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: 05102-3743
Category Name: Vacation Looks
Price: $10.00 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Check Me Out Mid-Rise Gingham Shorts
With these mid-rise gingham shorts, you'll be checking yourself out in every mirror you pass!
Fit & Features
- Gingham print, woven fabric
- Mid-rise waist
- Ruffled trim hem
- Runs true to size
Style Number/Barcode: 06303-000025
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Stunner Maxi Dress
Look at you stylish stunner! This berry hued maxi dress was made for you! It features a sleeveless bodice, tank-like shoulder straps, a deep V neckline and back, a high elastic banded waist with side cut out details, and a flowy, maxi length. The dress is composed of a linen fabric with no stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-3655
Category Name: Vacation Looks
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crochet Cutie Maxi Dress
Keep it cute in crochet! This no fuss maxi dress features a pewter hue, a sleeveless crochet bodice, a V neckline and adjustable narrow straps that lead to an open back design. Her relaxed fit bodice leads to an elongating maxi length skirt. Dress is composed of a lined lightweight woven fabric that offers minimal stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-3572
Category Name: Vacation Looks
Price: $10.00 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flowy Vibes Maxi Dress
Get those pretty flowy vibes this spring with this off the shoulder maxi dress! It features short ruffle sleeves, a square neckline, a hidden back zipper and hook and eye closure, a tie front belt, two front slits, and a long maxi length. The mauve dress is composed of a lightweight crepe fabric with a short knit lining.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-3571
Category Name: Vacation Looks
Price: $10.00 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish To The Maxi Dress
Be a fab fashionista and stylish to the max in this red maxi dress! It features a sleeveless bodice, a strapless square neckline, a high waist seam, slanted front pockets, pleated details, and a long, maxi fit. The dress is composed of a knit fabric and offers moderate stretch and a flowy, relaxed fit.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-3557
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Scoop Mini Dress
Basic never looked so good in this essential mini dress! It features a light blue color, a scoop neckline, tank-like straps and a mini length silhouette. Dress is composed of a double lined smooth knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3350
Category Name: Vacation Looks
Price: $13.91 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Smocked In Florals Mini Dress
Keep it sweet in florals! This pretty light blue dress features an off the shoulder neckline with ruffled trim, a sweetheart bust with a small tie front keyhole and short sleeves. The relaxed fit bodice features a smocked back and leads to a curve hugging mini length silhouette. The all over dainty floral print features pink and red hues. Dress is composed of a lightweight woven fabric that offers minimal stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0074
Category Name: Vacation Looks
Price: $10.00 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Smocked Mini Dress
Stay sweet with a little sass in this pretty smocked mini woven dress! It features an off the shoulder square neckline, short ruffled sleeves, a stretchy and smocked back, a top keyhole tie accent, and a curve hugging fit.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0100
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chambray Today Ruffle Mini Dress
As playful as it is party-ready, this casually chic chambray mini dress is going places. Dress features thick straps, square neckline, a ruffle hem, and smocking from bust through thigh. Dress is made from a lightweight cotton blend and offers plenty of stretch through the middle.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0139
Category Name: Vacation Looks
Price: $32.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Emerald City Cutout Mini Dress
Journey far and wide in this flirty, feminine mini dress. Dress features gathered ties at front and side, a waist cutout, ruffle detail at hem and gathered cap sleeves, and a back zip closure. Dress is lined and made from a lightweight woven fabric with little to no stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0131
Category Name: Vacation Looks
Price: $18.94 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Button Denim Mini
Streamlined and sweetly sophisticated, this lavender mini draws all eyes to you. Dress features a soft V neckline, button front, and adjustable spaghetti straps. Dress is made from a cotton-denim fabric and has minimal stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0116
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Button Like You Midi Dress
Button up in this one of a kind midi dress! The ivory dress features a V neckline, short sleeves with tie accents, princess seams a multi button down front with a tortoise shell hue, a cinching tie waist and a high low hemline with a ruffled trim. The back features a smocked fabric for a comfortable wear. Dress is composed of a lined lightweight woven fabric that offers a relaxed 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: 05102-0115
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Frilly In Florals Midi Dress
Keep it flirty and frilly in florals this season! This ivory dress features a sleeveless bodice, a square neckline, ruffled shoulder straps and a midi length skirt with side slit. The all over dainty floral print features blue hues. Dress is composed of a linen fabric.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0063
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Button Up In Ruffles Midi Dress
Button yourself up in pretty ruffles! This must have black dress features a sleeveless bodice, a plunging V neck with a tie front accent, ruffled shoulder straps and a multi button front with tortoise shell hued buttons. The midi length lets you show off your favorite heels! Dress us composed of a lined linen 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: 05102-0026
Category Name: Vacation Looks
Price: $10.00 $43.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Escape Lace-Up Espadrille Wedges
Strut looks pretty in these lace-up espadrille wedges while on vacation or weekend fun!
Fit & Features
- Wedge heel
- Square toe, crisscross straps
- Lace-up ankle straps
- Platform sole
- Espadrille material
- Runs true to size
Style Number/Barcode: 07406-000002
Category Name: Vacation Looks
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Button Down In Style Dress
Button down in style in this cute midi dress! The white dress features a square neckline, wide shoulder straps, a button down front, a tie waist belt, side pockets and a center high slit. Dress is composed of an unlined denim-like fabric that offers a form hugging 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: 05102-0059
Category Name: Vacation Looks
Price: $31.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Striped With Style Midi Dress
Get all striped with style with this adorable summer ready midi dress! It features a sleeveless bodice, a V neckline created by a wrap front, a partially stretchy and smocked back with a hidden zipper and hook and eye closure, a faux button down front, a waist tie, and a front slit. The mustard yellow dress is composed of lightweight woven fabric with no stretch and a short lining.Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0032
Category Name: Vacation Looks
Price: $15.00 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Side Up Skater Dress
This mustard yellow skater sundress is a definite must-have for this season! It features a sleeveless bodice, adjustable spaghetti straps, a square neckline, a hidden back zipper and hook and eye closure, a high waist seam, and a wrap skater skirt with a chic side tie. The dress is composed of a woven fabric with no stretch.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0054
Category Name: Vacation Looks
Price: $10.00 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Buttoned Up In Stripes Dress
Button up in stylish stripes! This pretty dress features a plunging V neckline, kimono sleeves, a cinching tie waist accent and a multi button down front with tortoise shell hued buttons that lead to an A-Line silhouette. The back features a matching plunging V shape, an adjustable bar strap detail and a hidden zipper closure. The all over stripe pattern features blue and white hues. Dress is composed of a lined gauze fabric that offers a relaxed fit with minimal stretch.
Style Number/Barcode: 05102-0040
Category Name: Vacation Looks
Price: $10.00 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Eyes On You Mini Dress
All eyes will be on you in this adorable eyelet mini dress! It has short puffy sleeves with elastic cuffs, a square neckline, faux button down details, a hidden zipper and hook and eye closure, a high waist seam, and a short, fitted look. The ivory dress is composed of a woven sheer eyelet fabric with a full lining.Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0001
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 Frenzy Open Back Maxi
Get caught up in pretty florals! This gray maxi dress features a sleeveless bodice, a square neckline, narrow shoulder straps and an open back with a narrow bar strap accent. The relaxed fit bodice leads to a curve hugging maxi length silhouette. The all over floral print is all you need to create a sweet look! Dress is composed of a knit fabric that offers 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: 05102-0004
Category Name: Vacation Looks
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hourglass Mini Dress
Get those golden hour selfies with this perf mustard yellow mini dress! It features a square neckline and back, short ruffle sleeves, a hidden back zipper and hook and eye closure, a high waist seam with two cut outs, and a woven lining. The dress is composed of a woven fabric with a floral eyelet pattern and no stretch.
Style Number/Barcode: 05102-0003
Category Name: Vacation Looks
Price: $10.00 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunner In Lace Midi Dress
Make a stunning entrance in this gorgeous lace midi dress! It features a flattering off-the-shoulder neckline with a sheer lace overlay, a high waist, and a mid-length, curve-hugging silhouette. Style this dress with pretty earrings and new heels for the perf bridal shower look!
Fit & Features
- Off-the-shoulder neckline, sheer lace overlay
- High waist
- Mid-length, form-hugging fit
- Sheer lace fabric, full knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05101-8850
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Off-the-shoulder neckline, sheer lace overlay