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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Pretty Pair Flower Stud Earrings
Tiny florals, major outfit charm. These flower stud earrings add the prettiest little pop to sundresses, slick buns, and every “just threw this on” look that secretly took planning.
Fit & Features
- Flower design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000425
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
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Sleek Shine Rhinestone Body Chain
Low effort, high shine—exactly the vibe. This sleek rhinestone body chain layers a cross-front drape over your look for that subtle but undeniable glow-up.
Fit & Features
- Dainty chain design
- Cross-front design
- Round rhinestone embellishments
- Baguette rhinestone embellishments
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000452
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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More Is More Five-Piece Ring Set
Why pick one ring when your hand can have a full personality. This five-piece ring set features textured shapes and colorful stone details for that effortlessly stacked look.
Fit & Features
- Five-piece ring set
- Structural designs
- Colored stone accents
- Polished metal finish
Style Number/Barcode: 07004-000124
Category Name: Vacation Looks
Price: $15.90
Availability: In Stock
Available Color: GOLD
Available Size: 7, 8
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Toast Worthy Tie-Back Skater Dress
Serving polished with a little extra flirt. This crepe skater dress hugs up top, flares just right, and lets the tie-back moment catch glances—perfect for bridal celebrations, graduations, and any dressy occasion!
Fit & Features
- Crepe fabric, smooth knit lining with stretch
- Plunge sweetheart neckline, padded bra cups
- Tank shoulder straps
- Back zipper and hook-eye closure, tie-waist design
- Drop waist seam
- Skater mini-length silhouette, godet paneling for flare
- Runs true to size
Style Number/Barcode: 05101-001040
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
Product Badge:- Best Seller
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Poolside Muse Bikini Halter Top
Serving beach plans with a little extra detail. This string bikini top layers into a cowl halter neck crop top with bead accents and an open back tie that feels playful, styled, and ready for sun-soaked moments.
Fit & Features
- Tie-dye print, mesh fabric
- Attached string triangle bikini top, bust lining, bead accents
- Halter cowl neckline
- Open tie back
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000725
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L
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Cherry On Top Lace Mini Dress
Pretty, playful, and impossible to ignore. This lace mini dress brings all the flirty details with ruffle trim, a dainty bust tie, and a twirl-worthy fit that feels straight out of a summer romance scene.
Fit & Features
- Lace fabric
- Ruffled trim keyhole tie square neckline
- Ruffled trim shoulder straps
- Lace-up back design
- Ruffled trim and lace front panels
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001059
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
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Summer State Floral Halter Top
Booked the outfit before the plans. This floral print halter top brings the heat with a plunging neckline and an open-hardware back, made for sunset dinners and beachside playlists.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Plunge halter neckline with tie straps
- Open back with hardware insert
- Fitted crop hem, ruched side seams
- Runs true to size
Style Number/Barcode: 06001-000559
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Bold Moves Cutout Maxi Dress
She’s bold, sculpted, and not here to blend in. This cutout maxi dress hugs in all the right places with a fluid drape that moves like you mean it.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Asymmetric waist cutout
- Ruched detailing
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001190
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Natalia Floral Halter Formal Dress
Special Occasion
Like wearable artwork made for golden hour arrivals, the Natalia floral mermaid gown brings soft romance and sculpted elegance together in one unforgettable silhouette. Designed with a plunging halter neckline, open strappy back, and dreamy oversized floral print, it’s the kind of look that turns every entrance into a moment.
Fit & Features
- Floral pattern, knit stretchy fabric
- Halter neckline
- Open back, bar accent straps and hook closure strap
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Wedding guests, vacations, anniversaries, formal milestone parties, honeymoons, destination celebrations, cocktail soirees, birthday dinners
Style Number/Barcode: 05002-000881
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: LAVENDER, FUCHSIA
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Island Twirl Crochet Mini Skort
Warning, this skort makes every walk a little more dramatic. This crochet mini skort features layered ruffle details and built-in shorts for the cutest mix of flirty and practical.
Fit & Features
- Crochet fabric, stretchy knit built-in shorts lining
- Low-rise drawstring waist tie
- Form-hugging fit
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06501-000122
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Knit Crush Tie Front Crop Top
Serving cozy with a little flirt built in. This crochet crop sweater ties at the front with a soft drape and flared sleeves that make it perfect for layering or wearing solo.
Fit & Features
- Sheer crochet soft knit fabric
- Tie-front neckline
- Flare long sleeves
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06005-000336
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Poolside Gossip Beaded Halter Top
This top definitely gets invited everywhere. The halter crop top features beaded strap details, a flirty keyhole front, and a body-skimming fit that pairs way too well with minis, linen pants, and vacation plans.
Fit & Features
- Stretchy knit fabric
- Halter scoop neckline, beaded accents, tie straps
- Bust keyhole cutout
- Open back
- Crop fitted hem
- Runs true to size
Style Number/Barcode: 06001-000598
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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All Eyes Strappy Rhinestone Mules
These understood the assignment—no notes. Strappy mule heels with rhinestone detailing bring just enough shine, while the sculpted heel keeps your look elevated from dinner to after plans.
Fit & Features
- Stiletto heel
- Square toe
- Rhinestone-embellished, asymmetrical straps
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000721
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: PINK, ORANGE, LIGHT, BLUE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Cool Confidence Denim Hot Shorts
These denim hot shorts bring the kind of confidence that makes every mirror check hit different. Designed with a fitted silhouette and extended tab waist, they’re the pair you throw on when basic bottoms just won’t cut it.
Fit & Features
- Denim fabric
- Mid-rise waist, belt loops
- Extended tab with dual button closures
- Hidden zipper closure
- Dual front and back pockets
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06603-000185
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Weekend Lineup Tie-Back Ruffle Romper
Floaty, flirty, and fully booked on your weekend lineup. This ruffle romper brings the drama with a twirl-worthy fit, open tie-back detail, and lightweight feel that’s made for rooftop dinners, birthday plans, and every photo op in between.
Fit & Features
- Lightweight woven fabric
- Sleeveless scoop neckline, ruffle trim, small keyhole cutout, tie-front detail
- Adjustable spaghetti straps
- Open tie-back design
- Fitted high waist
- Tiered ruffled overlay, flowy shorts
- Runs true to size
Style Number/Barcode: 06403-000130
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
- Lightweight woven fabric
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Serving Curves Animal Print Cutout Mini Dress
Serving curves with zero hesitation. This animal and floral print mini dress brings the drama with a plunging neckline, sultry cutouts, hardware details, and a fit that knows exactly what it’s doing.
Fit & Features
- Knit fabric with high stretch
- Abstract animal and floral print
- Sleeveless plunging V-neckline, dual hardware accents at the bust and waist
- Front waist cutout, ruched detailing
- Halter strap, open back
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000396
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Pretty Glow Moment Ombre Satin Clutch
Caught the light before you even walked in. This ombre satin clutch with allover colored rhinestones brings just enough shine to carry your whole look from dinner to night-out plans.
Fit & Features
- Dumpling clutch bag silhouette
- All-over colored rhinestone embellishments
- Detachable chain strap
- Top clasp closure
- Spacious lined interior
- Satin ombre-patterned material
Style Number/Barcode: 07204-000055
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
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Vacay Life Tropical Floral Mesh Maxi Skirt Coverup
Vacation outfit secured. This tropical floral mesh maxi skirt coverup brings the drama with a body-hugging fit, sheer finish, and side tie details that were made for beach clubs, bikini pics, and every “wait, where’d you get that?” moment.
Fit & Features
- Sheer mesh fabric, high stretch
- Tropical floral print
- Mid-rise waist
- Side cutouts, tie accents
- Maxi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07105-000058
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: ORANGE
Available Size: S, M, L
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Resort Mood Floral Print Halter Top
Serving resort mood without needing the plane ticket. This floral print halter top brings the vibes with a deep V-neckline, curve-hugging fit, and open-back moment that looks so good with capris, denim, or a mini skirt.
Fit & Features
- Knit fabric, high stretch
- Tropical floral print
- Sleeveless deep V-neckline
- Halter strap, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000610
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Tie Me Close Lace Maxi Skirt
A little reveal, a lot of intention. This lace maxi skirt features a front mesh wrap tie and a high side slit that moves with you and keeps the look feeling elevated but effortless.
Fit & Features
- Lace fabric, built-in knit panty lining
- High-rise waist
- Front mesh wrap tie design
- High side slit
- Form-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000153
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Palm Print Daydream Wide-Leg Pants
These tropical palazzo pants were made for beach clubs and poolside selfies, with its breezy fit and high-rise waist that keeps the vibe effortless while still looking fully put together.
Shop Matching Top: Palm Print Daydream Tie-Front Top
Fit & Features
- Palm print, knit, stretchy fabric
- High-rise waist
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000085
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: EMERALD
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Palm Print Daydream Tie-Front Top
This tropical tie-front top was made for beach clubs and poolside selfies, with its breezy fit and plunge neckline that keeps the vibe effortless while still looking fully put together.
Shop Matching Bottoms: Palm Print Daydream Wide-Leg Pants
Fit & Features
- Palm print, knit, stretchy fabric
- Short sleeves
- Tie-front neckline
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06202-000091
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: EMERALD
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Rylan Floral Linen Cutout A-Line Dress
Special Occasion
Made for sun-drenched celebrations, the Rylan floral linen A-line dress brings effortless glamour to every RSVP. The plunging neckline and sculpted cutout detail give the flowy silhouette a modern feel that’s perfect for vacations, birthday dinners, and chic brunch plans.
Fit & Features
- Linen-blend woven fabric
- Floral print, piping contrast design
- Sleeveless V-neckline, tank shoulder straps
- Tie-front detail, asymmetric front waist cutout, side cutouts
- Open back, tie-back strap, lower zipper with hook-eye closure
- Floor-length A-line silhouette
- Runs true to size
Where to Wear:
Birthday celebrations, vacations, honeymoons, summer parties, and brunch with the girls.
Style Number/Barcode: 05002-001150
Category Name: Vacation Looks
Price: $94.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Vacay Serve Tropical Floral Mesh Mini Dress Coverup
Serving vacation pics without even trying. This tropical floral mesh mini dress hugs in all the right places with a sheer bodycon fit that was made for beach clubs, rooftop drinks, and every “wait, where’d you get that?” moment.
Fit & Features
- Sheer mesh fabric, high stretch
- Large tropical floral print
- Sleeveless crew neckline
- Tank shoulder straps
- Ruched draped front design, O-ring accent
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 07105-000059
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: ORANGE
Available Size: S/M, M/L