A dress that does the flirting for you. The cutout crochet shows just enough, while the shell and sequin details add that subtle shimmer that catches light—and attention—without trying. This is your out-all-day, glow-all-night kind of maxi dress.
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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Sky Shimmer Sequin Lace-Up Top
This sequin crop top brings that easy, ethereal shimmer your outfit’s been begging for. The sequin print catches the light just right, while the lace-up back keeps everything cute, confident, and fully dance-floor approved. Shop the matching skirt.
Shop The Matching Skort: Sky Shimmer Sequin Mini Skirt
Fit & Features
- Sequin print fabrication with mesh texture
- Halter V-neckline
- Strappy lace-up open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-000236
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sand And Shine Triangle Bikini Top
This triangle bikini top brings that effortless “I woke up glowing” energy with its sleek abstract metal trim. Easy to tie, easy to style, and perfect for that sun-kissed moment you know is happening the second you hit the beach. Shop the matching bottoms.
Shop The Matching Bottoms: Sand And Shine Bikini Bottoms
Fit & Features
- Smooth stretch swim fabric
- Triangle cups with removable padding
- Abstract metal ring accent at the center front
- Adjustable halter neck ties
- Adjustable back tie closure
- Runs true to size
Style Number/Barcode: 07104-000013
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: RUST
Available Size: L
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Vacay Bloom Floral Mesh Halter Top
A halter top that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included.
Shop Matching Bottoms: Vacay Bloom Floral Mesh Maxi Skirt
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless plunging V-neckline
- Tie-back halter straps
- Open back, lower back strap with asymmetric metal hardware accent
- Ruching, mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000385
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Seaside Sweetheart Layered Necklace
Channel pure coastal energy with this layered charm necklace made for sunny days, salty breezes, and that effortless beach-babe vibe. Three delicate chains are stacked to perfection, each featuring its own seaside icon—an iridescent shell, a dainty starfish, and a polished cowrie charm.
Fit & Features
- Layered chain necklace design
- Gold-tone finish
- Seashell, starfish, and cowrie charms
- Lobster clasp closure
Style Number/Barcode: 07002-000245
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Attitude Cutout Mini Tube Dress
Sleek with a hint of attitude—this cutout tube dress leans into confidence without overdoing it. The smooth knit hugs effortlessly, while the cutout crisscross beading gives your waist that sculpted, stop-scrolling energy.
Fit & Features
- Smooth double-lined knit fabric, high stretch
- Strapless straight-across neckline
- Front waist cutout
- Asymmetric strappy design, beaded stone accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000359
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Shoreline Siren Hoop Cutout Swimsuit
This one-piece turns the beach into your runway with bold hoop cutouts and a plunge that knows exactly what it’s doing. The silhouette shapes, lifts, and flatters while giving you that effortless “I make swimwear look intentional” confidence.
Fit & Features
- One-piece swimsuit with O-ring cutout detailing
- Deep plunge neckline with adjustable halter ties, removable padded bra cups
- Open sides with high-cut leg
- Stretch swim fabric with minimal coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000016
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sand And Shine Bikini Bottoms
These bikini bottoms brings that effortless “I woke up glowing” energy with its sleek high-hip silhouette. Easy to slip on, easy to style, and perfect for that sun-kissed moment you know is happening the second you hit the beach. Shop the matching top.
Shop The Matching Top: Sand And Shine Triangle Bikini Top
Fit & Features
- High hip bikini bottom silhouette
- Scrunch back seam for shaping
- Smooth stretch swim fabrication
- Minimal coverage for a bold finish
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000021
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: RUST
Available Size: L
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Linked Up Luxe Oval Chain Belt
When your outfit needs that little something, this belt steps in like the finishing touch you didn’t know you were missing. The textured oval chain-link design brings effortless polish to everything from low-rise moments to dressed-up nights.
Fit & Features
- Textured oval-link design
- Lightweight metal construction
- Adjustable chain with lobster clasp closure
Style Number/Barcode: 07301-000348
Category Name: Vacation Looks
Price: $15.90
Availability: Out of Stock
Product Badge:- Ships Free
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Lyla Lace A-Line Formal Dress
Special Occasion
Designed for the woman who knows how to captivate a room, the Lyla formal dress pairs romantic lace fabric with an effortless a-line floor-length silhouette. The halter neckline with a rosette, side waist cutouts, and front ruffle trim slit creates a sculpted, eye-catching moment that feels equal parts daring and refined.
Fit & Features
- Lace fabric lined with stretchy mesh and knit
- Halter V-neckline with rosette trim
- Open back with tie, lower zipper and hook-eye closure
- Side waist cutouts
- Front ruffled trim slit
- A-line silhouette, floor-length hem
- Runs true to size
Where to Wear:
Weddings, destination celebrations, formal galas, black-tie charity balls, luxe cocktail parties, anniversaries, fashion-forward soirees, holiday events, opera or theatre nights, birthday dinners, resort evenings
Style Number/Barcode: 05002-000652
Category Name: Vacation Looks
Price: $49.97 $99.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S
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Vacay Vibes Geometric Knit Halter Mini Dress
Meet the mini dress that knows how to make an entrance without trying too hard. The geometric knit hugs just right, giving you that effortless, sculpted look for beach nights, rooftop drinks, and the best vacay vibes.
Fit & Features
- Sheer embroidered knit fabric, knit lining, high stretch
- Abstract geometric pattern, metallic woven threading
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000377
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Vacation Glow Floral Mesh Bodycon Mini Dress
Sun-kissed and ready to steal the scene, this floral mesh mini dress brings that radiant, vacation-glow confidence. The soft bodycon fit hugs just right, with a halter plunge neckline and a draped sash that make your arrival feel effortlessly iconic.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch, large floral print
- Sleeveless plunging V-neckline
- Tie-back halter straps, partially open back
- Ruched waist, asymmetric metal hardware accent
- Ruffled side sash
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000392
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Coastal Crush Cutout Crochet Maxi Dress
Fit & Features
- Sheer crochet knit fabric, mini-length knit lining, moderate stretch
- Sleeveless ruched knit top, no-slip strip, wired V-neckline
- Tie-back halter spaghetti straps, eyelet trim, shell and sequin embellishments
- Partially open back
- Maxi-length hem, high-cut side slit
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000360
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Flirty Mood Lace-Up Velvet Stiletto Heels
The kind of heels that flirt without trying. Made with plush velvet with dainty lace-up straps, they bring that subtle drama every outfit deserves—perfect for date nights, rooftop drinks, or when you just feel like turning heads.
Fit & Features
- Stiletto heel
- Open square-shaped toe
- Cutout toe strap design, thin metal accent
- Thin lace-up strappy design, tie closure
- Velvet material
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-000453
Category Name: Vacation Looks
Price: $12.97 $40.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN, IVORY
Available Size: 7, 7.5, 10
Product Badge:- Sale
- Stiletto heel
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Garden Bloom Flower Earrings
A little color, a lot of charm. These enamel flower stud earrings feature soft blue-and-white petals with a gold-tone finish—perfect for adding a touch of playful polish to any outfit.
Fit & Features
- Polished finish
- Enamel flower design with blue and white detail
- Post back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000204
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Chic Wide-Leg Pants
Meet the pants that move like you’ve got somewhere fun to be. The smooth knit fabric and wide-leg silhouette give you that breezy, pulled-together vibe, and you didn't even have to think about it. Pair with the matching tops.
Shop Matching Tops: Effortless Chic Lace-Up Crop Top, Effortless Chic Beaded Cowl Neck Top
Fit & Features
- Smooth knit fabric, high stretch
- High-rise waist
- Hip-hugging fit
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000065
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: RUST, WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Vacay Bloom Floral Mesh Maxi Skirt
A maxi skirt that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included.
Shop Matching Top: Vacay Bloom Floral Mesh Halter Top
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- High-rise waist
- Ruching
- High-cut side slit
- Maxi-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000102
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: S, M, L
Product Badge:- Part of a Set
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Sea Treasure Five-Pack Ring Set
Straight from the shore and made to stack. This five-pack sea life ring set brings coastal energy with faux pearl accents, starfish details, and seashell-inspired designs. The perfect finishing touch for your next beachy outfit—or destination celebration.
Fit & Features
- Five-pack ring set
- Starfish, seashell, floral, and sculptural designs
- Polished finish
Style Number/Barcode: 07004-000079
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Trio Earring Pack
Consider this your instant polish pack—the kind of trio that makes any outfit feel a little more thought-out without the effort. Lightweight, chic, and finished with a touch of shine, these earrings bring that easy everyday glow you’ll reach for again and again.
Fit & Features
- Three pack set
- Multi-colored design
- Square-shaped silhouette with gold trim
- Omega closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000228
Category Name: Vacation Looks
Price: $13.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sky Shimmer Sequin Mini Skirt
This sequin mini skirt brings that easy, ethereal shimmer your outfit’s been begging for. The sequin print catches the light just right, while the built-in shorts keep everything cute, confident, and fully dance-floor approved. Shop the matching top.
Shop The Matching Top: Sky Shimmer Sequin Lace-Up Top
Fit & Features
- Sequin print fabrication with soft texture, sewn-knit lining
- Mid-rise waist with fitted silhouette
- Mini length hem
- Hidden back zipper closure
- Runs true to size
Style Number/Barcode: 06401-000034
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: S, M, L
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Untamed Glam Mesh Maxi Dress
For nights when subtle just isn’t in your vocabulary, this mesh maxi dress delivers full-throttle confidence. The abstract animal print, plunging neckline, and hardware detail hit that perfect mix of daring and glam, while the bodycon fit keeps the silhouette sleek and unforgettable.
Fit & Features
- Abstract animal print, mesh fabric, short knit lining
- Plunging neckline with hardware detail
- Fitted long sleeves
- Bodycon maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000391
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Instant Cool Aviator Sunglasses
These aviators bring that “I didn’t try, but it worked” vibe every time. The structured plastic frame and bold lenses give you instant cool without stealing the show—perfect for errands, brunch, or dodging eye contact with someone you’re so done with.
Fit & Features
- Aviator-shaped frame
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000095
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Aubrey Lace Halter Mermaid Formal Dress
Special Occasion
Designed to turn heads, the Aubrey formal dress pairs delicate leopard floral lace with a sculpted halter neckline and wired plunge bodice for a confident, sculpted fit. Finished with a sweeping mermaid silhouette and front sash detail, it’s made for moments that deserve to be remembered.
Fit & Features
- Leopard, floral print, lace fabric, stretch knit lining
- Wired plunge halter neckline with tie closure
- Padded bra cups
- Low back, zipper and hook-eye closure
- Front sash accent, ruched mermaid silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Destination weddings, birthday celebrations, fashion-forward events, anniversaries, date nights, glam parties
Style Number/Barcode: 05002-000809
Category Name: Vacation Looks
Price: $39.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS
Product Badge:- Sale
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Goddess Glow Leaf Arm Cuff
Channel full ethereal goddess energy with this gold leaf arm cuff that wraps your arm in shimmering, nature-inspired detail. With its sculpted leaf tips and flexible wrap design, it adds an instant dreamy, boho-chic vibe to any look—dressy fits, vacations, nights out, you name it.
Fit & Features
- Gold-tone flexible wrap arm cuff
- Sculpted leaf accents on each end with rhinestones
Style Number/Barcode: 07003-000208
Category Name: Vacation Looks
Price: $13.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bloom Babe Abstract Floral Mesh Maxi Skirt
All eyes go straight to you in this blooming floral maxi skirt that is both sweet and unapologetically bold. The ruched mesh hugs your shape with that sleek, confident fit you reach for on every hot-girl outing.
Shop Matching Top: Bloom Babe Abstract Floral Mesh Corset Top
Fit & Features
- Mesh fabric, high stretch
- Abstract floral print
- High-rise waist
- Back slit
- Maxi-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000051
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set