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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After Hours Floral Leopard Mini Dress
Fluid, flattering, and impossible to ignore. This halter mini dress mixes floral and leopard-inspired abstract prints with ruched details and cascading ruffles that have all eyes on you.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Floral leopard print
- Ruffled trim V-neckline, halter tie-back straps, partially open back
- Ruffled trims, ruched detailing
- Mini-length asymmetric hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-000689
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sharp Turn Aviator Sunglasses
Sleek lines, zero effort required. These trendy aviator sunglasses bring a modern edge to everyday looks, with a bold frame that instantly pulls everything together—from casual errands to styled-up moments.
Fit & Features
- Sleek aviator silhouette
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000127
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Bloom Cowl Halter Maxi Dress
Bold print, barely-there feel perfect for vacations. This maxi dress blends leopard and tropical florals with a plunging cowl halter and open back, finished with a statement floral hardware that stands out.
Fit & Features
- Tropical floral and leopard print
- Sheer mesh fabric, soft knit short lining
- Plunge cowl halter neckline
- Open back, lower ruched seam
- Front tropical floral hardware piece
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000401
Category Name: Vacation Looks
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunlit Plans Halter Tiered Skater Dress
Soft, flirty, and made for daylight plans that turn into something more. This halter skater dress balances a sculpted top with a playful tiered skirt for an easy look that feels styled the second you slip it on.
Fit & Features
- Smooth stretch fabrication
- Halter neckline with scoop front
- Drop waist with tiered skater skirt
- Mini length silhouette
- Runs true to size
Style Number/Barcode: 05102-000457
Category Name: Vacation Looks
Price: $9.97 $43.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Mode Abstract Open Back Maxi Dress
This dreamy mesh maxi dress was made for golden hour plans, tropical cocktails, and dancing 'til dinner. Designed in an abstract print that brings the ocean and desert sky together, this halter dress features a draped cowl neckline, hardware straps, and open tie-back.
Fit & Features
- Abstract print, mesh-lined fabric
- Plunge cowl halter neckline with hardware
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000409
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Focus Florals Mesh Maxi Dress
Soft-focus florals, but make it a statement. This floral mesh maxi dress hugs just right with a sleek, fitted silhouette that’s ready for weddings, date nights, and every dressed-up plan on your calendar.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Fitted silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000363
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Sheer mesh fabric with knit lining, high stretch
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Pretty Agenda Floral Woven Ruffle Maxi Dress
Soft, flowy, and ready for every RSVP on your calendar. This pretty floral woven maxi dress brings effortless drama with tiered ruffles and a flattering sweetheart neckline that looks just as good in photos as it does in motion.
Fit & Features:
- Lightweight woven fabric with full-length stretchy knit lining
- All-over floral print
- Sleeveless sweetheart neckline with ruched bust, adjustable tank straps
- Open back with self-tie detail, lower back zipper with hook-eye closure
- Tiered ruffled design
- Maxi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000876
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Lightweight woven fabric with full-length stretchy knit lining
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Flirty Babe Polka Dot Mesh Ruffle Mini Dress
Flowy, flirty, and impossible to ignore. This polka dot mesh ruffle mini dress hugs in all the right places with soft ruching and a playful hem that moves with you.
Fit & Features:
- Mesh fabric with knit lining, high stretch
- All-over polka dot print
- Sleeveless plunging V-neckline
- Tie-back halter straps, partially open back
- Ruched body, drop waist design
- Tiered ruffled mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000515
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Mesh fabric with knit lining, high stretch
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Sunkissed Ruffles Floral Mini Dress
Made for slow walks through seaside towns and golden hour selfies. This floral mini dress brings soft romantic vibes with a sweetheart neckline and tiered ruffles that move with you.
Fit & Features
- Chiffon fabric with floral print, knit lining
- Ruched sweetheart neckline with adjustable spaghetti straps
- Ruched fitted bodice with back zipper and hook-eye closure
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000558
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Plans Chevron Crochet Maxi Dress
This chevron crochet knit maxi dress features a flattering V-neck and lace-up back that feels equal parts stylish and unforgettable—perfect for beachside restaurants or warm nights out.
Fit & Features
- Chevron striped pattern
- Crochet knit lined fabric
- V-neck, spaghetti straps
- Lace-up back
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000418
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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One And Done Halter Wide Leg Jumpsuit
Slip it on and let the silhouette do the work. This knit cutout halter wide-leg jumpsuit hugs where it should, flows where it matters, and delivers instant confidence from day plans to night.
Fit & Features
- Lined knit stretch fabric
- Halter neckline with tie closure
- Cutout bodice
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000074
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Alluring Chic Ribbed Knit Belted Mini Dress
Confident curves, chic allure. This ribbed knit mini dress hugs in all the right places with a belted waist that pulls the look together for nights out, date plans, or anytime you want effortless polish with a little edge.
Fit & Features
- Ribbed knit fabric with high stretch
- Sleeveless scoop neckline
- Tie-back halter straps, partially open back
- Attached O-ring belt detail at the waist
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000315
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Confidently Bold Strappy Faux Leather Tube Top
Confidently bold will be your vibe in this strappy faux leather tube top. It hugs you in all the right places and turns even a low-effort outfit into something undeniably intentional.
Fit & Features
- Strapless bandeau silhouette
- Front cutout with strappy wrap detail
- Lace-up back for adjustable fit
- Mid-length hem, form-hugging fit
- Faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-000216
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beachside Bold Abstract Print Beaded Bikini Top
Sun on your skin, confidence on repeat. This abstract print bikini top brings a cool edge with beaded details that feel styled and trendy—perfect for beach days that turn into golden-hour plans. Pair with the matching bikini bottoms.
Shop Matching Bottoms: Beachside Bold Abstract Print High-Cut Bikini Bottoms
Fit & Features
- Smooth stretch knit fabric, abstract print
- Triangle design
- Beaded accents on the straps and at the center
- Adjustable spaghetti straps
- Tie-back straps
- Runs true to size
Style Number/Barcode: 07104-000017
Category Name: Vacation Looks
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Confidence Animal Print Halter Top
A halter top that knows exactly what it’s doing—draped, sculpted, and ready to flex your confidence. The mesh fabric and abstract animal print bring that cool-girl edge. Style with the matching maxi skirt.
Shop Matching Bottoms: Cool Confidence Animal Print Mesh Maxi Skirt
Fit & Features
- Mesh fabric, high stretch
- Abstract animal print
- Sleeveless plunging cowl neckline, bar strap detail
- Tie-back halter spaghetti straps
- Open back, lower tie-back spaghetti straps
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000387
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Vibes Animal Print Halter Top
A little daring, a lot confident—this top does not blend in. The draped halter neckline and curve-hugging fit make it a go-to for nights out, styled up with the matching skirt or worn solo when the vibe calls for extra.
Shop Matching Skirt: Untamed Vibes Animal Print Maxi Skirt
Fit & Features
- Smooth knit fabrication
- Sleeveless halter cowl neckline
- O-ring accents
- Lower back tie-back
- Leopard and snake print
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000469
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Weekend Cool Mid-Rise Denim Jorts
Casual but never boring—these are the jorts you throw on and somehow look styled. The relaxed mid-rise fit keeps things easy while still feeling intentional for brunch, errands, or off-duty hangs.
Fit & Features
- Structured denim fabrication
- Mid-rise waist
- Single button and hidden zipper closure
- Relaxed jort silhouette
- Knee-length hem
- Five-pocket styling, belt loop accents
- Runs true to size
Style Number/Barcode: 06603-000146
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: MED, DENIM
Available Size: S, L
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Sweet Plans Eyelet Skater Dress
Soft, flirty, and very much ready for plans. This eyelet skater dress brings that effortless charm with a flattering fit that feels easy, romantic, and wearable from day dates to sunset strolls.
Fit & Features
- Lightweight eyelet fabric with soft lining
- Square neckline with adjustable bust tie detail
- Sleeveless silhouette with wide straps
- Fitted bodice with zip back closure
- Flowy skater skirt with subtle tiered seam
- Runs true to size
Style Number/Barcode: 05101-000952
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Beauty Floral Halter Maxi Dress
Bring the drama—this halter maxi dress mixes fierce animal print with bold florals for a look that’s equal parts wild and romantic. With its plunging neckline and curve-skimming fit, it’s ready for dinner downtown, rooftop hotel cocktails, or every moment you want to own.
Fit & Features
- Floral print design, mesh-lined stretchy fabric
- Plunge halter neckline
- Cutout bodice
- Curve-hugging silhouette with high slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000685
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Made for the Moment Floral Maxi Dress
Floaty, romantic, and made to move. This floral midi dress features cascading ruffles and a front slit that brings just enough drama while still feeling light, polished, and wearable for dressed-up plans.
Fit & Features
- Lightweight chiffon fabric with floral pattern
- Slim-fit sweetheart bodice with spaghetti straps
- Adjustable tie-back detail for customizable fit
- Front slit with cascading ruffle trim
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000951
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Postcard Pretty Halter Cutout Maxi Dress
Booked the dinner, ordered the spritz, now you need the dress. This halter maxi dress brings the drama with a rose detail, front cutout, and tiered skirt that moves like you planned this all along.
Fit & Features
- Lightweight woven fabric with abstract print
- Halter neckline with rosette detail
- Front cutout with twist front bodice
- Smocked back for stretch
- Tiered ruffled maxi skirt
- Runs true to size
Style Number/Barcode: 05102-000411
Category Name: Vacation Looks
Price: $28.97 $62.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS
Product Badge:- Sale
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Sun Chasing Ribbed Knit Halter Midi Dress
Hot plans? Found the dress. This ribbed knit halter bodycon midi dress hugs in all the right places with a ruched bust and flirty keyhole cutout—aka your go-to for birthday dinners, rooftop nights, and every RSVP in between.
Fit & Features
- Ribbed sweater knit fabric, high stretch
- Sleeveless sweetheart neckline
- Tie-back halter spaghetti straps
- Ruched bust, keyhole cutout
- Midi-length hem, high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000286
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Crush Beaded Thong Sandals
POV you’re five minutes from the beach, and your outfit is already winning. These beaded thong sandals keep it easy with a flat sole and shell inspired details that instantly elevate your warm-weather lineup.
Fit & Features
- Smooth faux leather upper
- Thong sandal silhouette
- Beaded strap with shell-inspired accents
- Flat sole with slip-on design
- Runs true to size
Style Number/Barcode: 07404-000065
Category Name: Vacation Looks
Price: $20.90
Availability: Out of Stock
Product Badge:- Ships Free
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Beachside Bold Abstract Print High-Cut Bikini Bottoms
Sun on your skin, confidence on repeat. These abstract print bikini bottoms bring a cool edge that feels styled and trendy—perfect for beach days that turn into golden-hour plans. Pair with the matching bikini top.
Shop Matching Top: Beachside Bold Abstract Print Beaded Bikini Top
Fit & Features
- Smooth stretch knit fabric, abstract print
- High-cut design
- Ultra-cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000025
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free