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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Alaiya Floral Chiffon Ruffle A-Line Dress
Special Occasion
Light, airy, and made for your most picturesque plans, the Alaiya floral chiffon A-line dress moves like a breeze with every step. Designed with soft ruffles, a romantic halter neckline, and a lace-up back detail, it’s the kind of dress that turns a simple entrance into a moment.
Fit & Features
- Floral-printed chiffon fabric with full-length lining
- Sleeveless sweetheart neckline, padded bust, ruched detailing
- Halter tie-back straps
- Open back, lower lace-up back design with tie closure, lower back zipper with hook-eye closure
- Floor-length A-line silhouette, flowy ruffled accents
- Runs true to size
Where to Wear:
Birthday celebrations, bridal showers, honeymoons, vacations, garden parties, and dressed-up dinners.
Style Number/Barcode: 05002-001450
Category Name: Vacation Looks
Price: $19.97 $129.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M
Product Badge:- Sale
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Major Fling Flutter Sleeve Maxi Dress
Fling into the spring season in this maxi dress that has an effortlessly breezy feel, while the V-neck and cutout back give it that easy, getaway-ready charm.
Fit & Features
- Airy cotton fabric, woven lining
- Flutter short sleeves
- V-neckline
- Cutout back
- Ruffled tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000748
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Dinner Plans Sleeveless Maxi Dress
This crewneck maxi dress hugs your shape with a soft shimmer finish and adjustable side ties atop flirty slits, making it your go-to for dinner plans, vacations, or beach nights.
Fit & Features
- Lurex knit fabric
- Sleeveless crewneck
- Adjustable side ties and high slits
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05103-000854
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: GOLD
Available Size: XS, S, L
Product Badge:- Sale
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Pretty In Motion Halter Mini Dress
Caught a vibe and dressed for it. This halter mini dress cinches at the waist with a flowy A-line skirt that moves with you—perfect for weekends that start with plans and end wherever.
Fit & Features
- Smooth stretch material
- Halter neckline with open back, tie straps
- Ruched waist detail
- A-line mini silhouette with pleated skirt
- Runs true to size
Style Number/Barcode: 05102-000358
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: ROYAL
Available Size: XS, S, M, L
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Tropic Heat Floral Mini Dress
Serving vacation energy even if you’re not booked yet. This floral mesh dress contours your shape with a plunging neckline and open back that does all the talking.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000625
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easy Going Distressed Denim Shorts
Your throw-on-and-go pair of denim shorts! These distressed denim shorts sit just right, with a laid-back fit that works from coffee runs to sunny-day plans.
Fit & Features
- Denim fabric, minimal stretch
- Mid-rise waistband
- Distressed accents
- Cutoff hem
- Front button and hidden zipper closure, belt loop accents
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-000209
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: MED, DENIM
Available Size: 5, 7, 9, 11, 13
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Weekend Mood Long Sleeve Tie-Front Crop Top
Serving just enough with zero overthinking. This long sleeve tie-front crop top drapes just right with a soft, stretchy feel that works from casual hangs to dressed-up nights. Style with the matching pants.
Shop Matching Bottoms: Weekend Mood High-Rise Pants
Fit & Features
- Sleek knit fabric, high stretch
- Long bishop-style sleeves
- V-neckline, tie-front closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-000094
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Part of a Set
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Cutie Vibe Lace Strapless A-Line Mini Dress
Cute plans only—this one’s already booked. This lace strapless A-line mini dress hugs up top and flares out with an easy, flirty fit that’s made for last-minute invites.
Fit & Features
- Sheer lace fabric with knit lining, high stretch
- Strapless straight-across neckline
- Mini-length asymmetric hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000492
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Hot Girl Summer Denim Bikini Top
It's looking like a hot girl summer with this denim bikini top. From the belted tube neckline to the front keyhole cutout, this swim top will be sizzling by the water!
Shop Matching Bottoms: Hot Girl Summer Denim Bikini Bottom
Fit & Features
- Denim swim fabric
- Belted strapless tube neckline
- Keyhole front cutout
- Fitted hem
- Runs true to size
Style Number/Barcode: 07104-000032
Category Name: Vacation Looks
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Bloom Flower Statement Stud Earrings
Chic, pretty, and a little extra—in the best way. These flower statement stud earrings bring a dreamy finish to your look, perfect for brunch plans, date nights, or whenever you want something that feels effortlessly styled.
Fit & Features
- Epoxy resin material, metal material
- Large statement flower design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000353
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Breeze Tie-Front Crop Top
Light, flowy, and just a little flirty—this tie-front crop top gets the vibe right every time. The airy feel and easy fit make it your go-to for warm days. Style with the matching wide-leg pants.
Shop Matching Bottoms: Soft Breeze Wide-Leg Pants
Fit & Features
- Airy woven fabric, no stretch
- Short billowy sleeves
- V-neckline, tie-front design
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06204-000128
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Soft Breeze Wide-Leg Pants
Light, flowy, and just a little flirty—these wide-leg pants get the vibe right every time. The airy feel and easy fit make it your go-to for warm days. Style with the matching tie-front top.
Shop Matching Top: Soft Breeze Tie-Front Crop Top
Fit & Features
- Airy woven fabric, no stretch
- High-rise waist
- Dual front pockets
- Pleated design
- Wide-leg silhouette
- Flowy fit
- Runs true to size
Style Number/Barcode: 06402-000032
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Part of a Set
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Weekend Bloom Floral Mesh Skater Dress
This is what you throw on when the invite says “cute but effortless.” The floral mesh skater dress hugs just enough up top, then flares for that easy, flowy vibe perfect for brunch plans or last-minute date nights.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Floral velvet burnout pattern
- Sleeveless V-neckline
- Spaghetti straps, open strappy back design, tie closure
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001007
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Story Floral Mini Dress
Booked, busy, and dressed for it. This floral print chiffon mini dress features a halter sweetheart neckline with a cutout bar back and tiered ruffled a-line hem made for vacations, bachelorette trips, and dressy occasions!
Fit & Features
- Floral print, chiffon fabric, woven lining
- Sweetheart halter neckline, padded bra cups, tie straps
- Cutout smocked bar back detail
- Tiered ruffled A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000856
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: L
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Getaway Ready Floral Print Maxi Dress
Out of office and not checking. This floral hem print maxi dress features a plunge halter neck, front slit, and a cross strap back that brings the drama from every angle. Perfect for packing with you on vacations, honeymoons, or weekend escapes!
Fit & Features
- Smooth knit stretchy fabric, knit lining
- Halter plunge neckline, hardware insert, adjustable cross back straps
- Open back design
- Cutout bosdice
- Flowy maxi-length silhouette with floral hem print
- Runs true to size
Style Number/Barcode: 05102-000576
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charmed Life Eyelet Skater Mini Dress
This skater dress just made your weekend cuter. It's designed to cinch you in with a flirty tie-front and opens up in the back for that effortless, pretty-from-every-angle moment.
Fit & Features
- Eyelet knit fabric
- Sweetheart tie-front neckline
- Puff short sleeves
- Strappy open tie-back design
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000892
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
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Vacation Glow Floral Satin Maxi Dress
This is the satin maxi dress that quietly steals the whole moment. Silky, draped, and barely-there in the back, this floral dress moves like you planned the entrance—even if you didn’t.
Fit & Features
- Floral print, silky satin fabric
- Cowl neckline
- Spaghetti straps
- Open cross back design
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000811
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: XXS, XS, S, M, L
Product Badge:- Sale
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Trina Abstract Animal Print Formal Dress
Special Occasion
The Trina abstract leopard print chiffon gown moves with every step and catches the light in all the right ways. Designed with a plunge V-neck with hardware, a cutout bodice, and a flowing A-line fit, it’s the kind of piece that makes the RSVP feel like your moment.
Fit & features
- Abstract animal print, chiffon-lined fabric
- Plunge V-neckline, hardware insert
- Cutout bodice with beaded strap detail
- Back zipper and hook-eye closure
- High front slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Prom, weddings, destination celebrations, vacations, cocktail dinner party, upscale birthday, resort evening events, engagement parties
Style Number/Barcode: 05002-001428
Category Name: Vacation Looks
Price: $109.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Sunkissed Energy Beaded Bikini Bottom
Booked, busy, and already by the pool. This bikini bottom brings the vibe with an adjustable side tie and statement bead details that instantly upgrade your swim rotation.
Shop Matching Top: Sunkissed Energy Beaded Bikini Top
Fit & Features
- Knit-lined fabric
- Adjustable side ties with beads
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000052
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: L
Product Badge:- Sale
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Sunkissed Energy Beaded Bikini Top
Booked, busy, and already by the pool. This bikini bottom brings the vibe with an adjustable side tie and statement bead details that instantly upgrade your swim rotation.
Shop Matching Bottoms: Sunkissed Energy Beaded Bikini Bottom
Fit & Features
- Knit-lined fabric
- Halter adjustable beaded straps
- Padded bra cup inserts
- Runs true to size
Style Number/Barcode: 07104-000035
Category Name: Vacation Looks
Price: $11.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Emily Floral Open Back Formal Dress
Special Occasion
The Emily mesh mermaid gown hugs in all the right places with a sculpted silhouette and striking hardware cutout detail. The ruched finish and halter neckline bring just the right amount of drama—perfect for when the RSVP calls for something unforgettable.
Fit & Features
- Floral print, mesh-lined fabric
- Halter sweetheart neckline with tie straps
- Open back
- Cutout bodice with hardware insert
- Ruched mermaid silhouette
- Floor-length hem
- Runs true to size
Where to Wear
Bridal celebrations, engagement photoshoots, garden parties, birthday brunches, rehearsal dinners, honeymoons, vacations, formal celebrations
Style Number/Barcode: 05002-001399
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L
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Summer Tropical Strappy Formal Dress
Special Occasion
The Summer dress pairs a sleek satin mermaid fit with a bold tropical floral print that feels equal parts polished and unforgettable. Mini rhinestone embellishments catch the light with every step, while the strappy back detail adds an unexpected, head-turning finish.
Fit & Features
- Tropical floral print, smooth-lined knit fabric with stretch
- Mini rhinestone embellishments
- Strapless neckline, non-slip grip lining, padded bra cups
- Bungee strappy back with mini hoop inserts
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, honeymoons, vacations, resorts, outdoor soirees, prom
Style Number/Barcode: 05002-001532
Category Name: Vacation Looks
Price: $19.97 $74.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M
Product Badge:- Sale
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Amy Floral Rhinestone Mesh Formal Dress
Special Occasion
Made for the kind of entrance that lingers, the Amy mesh mermaid gown shimmers with all-over mini rhinestone embellishments and a tropical floral print that feels both bold and refined. A scoop neckline, delicate spaghetti straps, and lace-up open back contour into a ruched, floor-length silhouette designed to captivate from every angle.
Fit & Features
- Tropical floral print, mini rhinestone embellishments
- Mesh-lined fabric with high stretch
- Scoop neckline, padded bra cups, spaghetti straps
- Lace-up open back
- Ruched mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Prom, vacations, destination weddings, honeymoons, resorts, sunset receptions, birthday dinners, date nights, engagement parties
Style Number/Barcode: 05002-001331
Category Name: Vacation Looks
Price: $39.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S
Product Badge:- Sale
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Day To Night Skater Mini Dress
From daytime events to evening celebrations, this skater mini dress keeps it easy and flattering with adjustable straps and dart seams that create a flared look. Just add heels or strappy sandals.
Fit & Features
- Textured woven fabric with stretch
- Square neckline, lined bust
- Adjustable spaghetti straps
- Flared skater silhouette with godet seams
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001226
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale