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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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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Perfect Plus One Platform Mules
Your warm-weather plans just found their perfect plus-one. This raffia platform mules brings that effortless vacation energy with a chunky heel and a belted strap that adds trendy flair to any look.
Fit & Features
- Chunky block heel
- Square toe
- Wide strap with a belted accent
- Cushioned insole
- Raffia material
- Runs true to size
Style Number/Barcode: 07401-000632
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: NATURAL
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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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: $29.90
Availability: In Stock
Available Color: DENIM
Available Size: M, L
Product Badge:- Best Seller
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Hot Girl Summer Denim Bikini Bottom
It's looking like a hot girl summer with these denim bikini bottoms. From the belted low-rise waist to the cheeky bottom, these swim bottoms will be sizzling by the water!
Shop Matching Top: Hot Girl Summer Denim Bikini Top
Fit & Features
- Denim swim fabric
- Belted low-rise waist
- Cheeky bottom
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000046
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: DENIM
Available Size: S, M, L
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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: In Stock
Available Color: LIGHT, BLUE
Available Size: NS
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Sunlit Shine Stone Thong Sandals
Minimal effort, maximum polish—these sandals are your throw-on-and-go kind of cute. Designed with stone embellishments and a sleek thong silhouette, they instantly elevate your vacation or weekend look.
Fit & Features
- Square toe
- Colored stone-embellishments, thong strap
- Cushioned insole
- Flat sole
- Metallic faux leather material
- Runs true to size
Style Number/Barcode: 07404-000069
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: GOLD
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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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: XS, 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: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Best Seller
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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: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, 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: $19.97 $64.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M
Product Badge:- Sale
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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: $45.90
Availability: In Stock
Available Color: PINK
Available Size: XXS, XS, S, M, L
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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: $26.90
Availability: In Stock
Available Color: ORANGE
Available Size: S, M, L
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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: $32.90
Availability: In Stock
Available Color: ORANGE
Available Size: S, M, L
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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: $74.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
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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: $79.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Ships Free
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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: 05101-001225
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: NAVY
Available Size: L
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Sunday Best Eyelet Floral Skater Dress
Invite secured, outfit handled. This eyelet floral mini dress is light, flirty, and made for dressy brunches, showers, and graduations.
Fit & Features
- Eyelet woven fabric, floral print, stretchy knit lining
- V-neckline, tie front bust keyhole
- Adjustable spaghetti straps
- Stretchy smocked back
- Tiered ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001078
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Sweet Timing Ruffled Mini Romper
This swiss dot mini romper cinches at the waist and flares out just right for that easy, cute, ready-in-five look. Just add heels or sandals for any celebration or daytime event.
Fit & Features
- Swiss dot woven lined fabric
- Square neckline with tie front
- Spaghetti straps
- Smocked stretchy waist
- Layered ruffle mini-length hem
- Built-in shorts lining
- Runs true to size
Style Number/Barcode: 06303-000046
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: WHITE, LIGHT, BLUE
Available Size: XS, S, M, L
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Sunlit Escape Cutout Mini Dress
This strapless mini dress feels like a vacation—even if you’re just stepping out. The strapless neckline keeps it clean, while the beaded detailing and side cutout bring an unexpected flair.
Fit & Features
- Linen-like fabric
- Strapless tube neckline
- Side cutout with a beaded design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000444
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L