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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Beachside Siren Mesh Swim Cover Up
Beach walk, but make it cinematic. This mesh cinched cover up hugs in all the right places with adjustable side ties and a dramatic slit, perfect for layering over your bikini when you want a little mystery with your moment.
Fit & Features
- Lightweight sheer mesh fabric
- Fitted maxi cover-up silhouette
- Mid-rise waist
- High side slit
- Ruched accents
- Runs true to size
Style Number/Barcode: 07105-000038
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: S/M, L/XL
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Sun Chaser Studded Bandeau Bikini Top
Sun out, standards high. This bandeau bikini top keeps it sleek with a halter strap detail and subtle stud trim, giving you that sculpted, secure fit whether you’re beach lounging or chasing the next swim pic.
Shop Matching Bottoms: Sun Chaser Studded Bikini Bottoms
Fit & Features
- Smooth stretch fabrication
- Bandeau bikini top silhouette
- Halter neck strap for added support
- Studded trim
- Runs true to size
Style Number/Barcode: 07104-000019
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Sun Chaser Studded Bikini Bottoms
Minimal effort, maximum effect. These studded bikini bottoms sit low on the hips with a flattering high cut leg, giving you that elongated look while the subtle hardware detail ties the whole swim set together.
Shop Matching Bikini Top: Sun Chaser Studded Bandeau Bikini Top
Fit & Features
- Smooth stretch fabrication
- Low-rise waist
- Studded trim
- Cheeky coverage
- Runs true to size
Style Number/Barcode: 07105-000028
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Mia Metallic Halter Slit Formal Dress
Special Occasion
For nights that call for something unforgettable, the Mia dress delivers liquid shine and sculpted allure in every step. Crafted in metallic knit with a plunge halter neckline, open back, and high side slit, this form-hugging long hem silhouette is equal parts sultry and refined.
Fit & Features
- Metallic slinky knit stretch fabric
- Plunge halter neckline
- Open back
- High side slit
- Form-hugging, long-length silhouette
- Runs true to size
Where to Wear:
Vacations, cocktail parties, birthday dinners, honeymoons, date nights, bachelorettes
Style Number/Barcode: 05002-001166
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: METALLIC
Available Size: XXS, XS, S, M, L, XL
Product Badge:- Ships Free
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Whimsical Charm Butterfly Claw Clip Set
Your five-minute hair routine just got a glow up. This four-piece butterfly claw clip set adds a dreamy, throwback touch to messy buns, half-up styles, and everything in between—cute, effortless, and always camera ready.
Fit & Features
- Four-piece hair claw clip set
- Butterfly designs
- Claw clip closure
Style Number/Barcode: 07006-000119
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Glow Satin Thong Sandals
Every detail does the most in the best way. These satin thong sandals add instant personality with colored rhinestones along the strap, perfect for day or night plans to add a little extra sparkle.
Fit & Features
- Round toe silhouette
- Slim thong toe strap with colored rhinestones
- Flat sole
- Satin material
- Runs true to size
- Available in assorted colors and a leopard print
Style Number/Barcode: 07404-000044
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: LEOPARD, PINK, RED, BLUE
Available Size: 5.5, 7, 7.5, 8.5, 9, 10, 6, 6.5, 8
Product Badge:- Sale
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Bloom Agenda Floral Mesh Halter Maxi Dress
RSVP secured and outfit handled. This floral mesh halter maxi dress sculpts with high-stretch comfort, features a statement flower hardware accent, and serves a partially open back that’s perfect for photo ops.
Fit & Features
- Sheer mesh fabric with full-length knit lining, high stretch
- Large floral print
- Sleeveless halter neckline, tie-back design
- Metal flower hardware accent
- Partially open back
- Maxi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000881
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Compliment Me Lace Ruffle A-Line Mini Dress
This lace ruffle A-line mini dress hugs through the sweetheart bodice, shows just enough with waist cutouts, and flares into a floaty silhouette that moves when you do—perfect for parties, bridal events, or any time you want compliments on repeat.
Fit & Features
- Sheer lace fabric with lining
- Sleeveless sweetheart neckline
- Tie-back halter straps, partially open back
- Asymmetric waist cutouts leading to open lower back
- Ruffled trim
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000867
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Soft Glam Agenda Lace Ruffle Skater Dress
Soft glam just secured your weekend plans. This lace skater dress hugs at the waist, flares into flirty ruffles, and is basically made for date night, birthday dinners, and any invite that says “dress cute.”
Fit & Features
- Lace fabric with lining
- Sleeveless deep V-neckline
- Halter tie-back straps
- Open back
- Tiered ruffled design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001100
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: PINK
Available Size: XXS, XS, L
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DIME Retro Slim Sunglasses
Serving vintage energy with a modern edge. These DIME slim rectangular sunglasses feature a rich mocha hue frame with tinted lenses that instantly elevate any look—from coffee runs to coastlines.
Fit & Features
- Slim rectangular frame
- Tinted lenses
- 100% UV protection
- Lightweight feel
- "Dime" logo on the arms
Style Number/Barcode: 07008-000144
Category Name: Vacation Looks
Price: $30.00
Availability: Out of Stock
Product Badge:- Ships Free
- Slim rectangular frame
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DIME Glendale Shield Sunglasses
If the invite calls for sunny day fun, these are coming with you. These DIME oversized shield sunglasses bring bold energy with a mirrored lens and sleek arms that instantly level up any look.
Fit & Features
- Lightweight frames
- Oversized shield silhouette
- Mirrored tinted lens
- 100% UV protection
- Slim arms with "Dime" logo
Style Number/Barcode: 07008-000140
Category Name: Vacation Looks
Price: $30.00
Availability: Out of Stock
Product Badge:- Ships Free
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DIME Cat Eye Sunglasses
Minimal effort, maximum attitude. These DIME sleek cat eye sunglasses feature a sharp silhouette and polarized tinted lenses that instantly elevate leather jackets, slick buns, and last-minute dinner plans.
Fit & Features
- Glossy acetate frame
- Narrow cat eye silhouette
- Polarized tinted lenses with 100% UV protection
- Slim arms with "Dime" logo
Style Number/Barcode: 07008-000139
Category Name: Vacation Looks
Price: $30.00
Availability: Out of Stock
Product Badge:- Ships Free
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DIFF Aspyn Ovard Tortoise Sunglasses
POV: you just found the sunglasses that pull the whole outfit together. These DIFF oval sunglasses add instant cool to your everyday looks, whether you’re headed to brunch, campus, or a last-minute photo dump moment.
Fit & Features
- Smooth acetate material
- Structured oval sunglasses silhouette
- Tinted lenses with 100% UV protection
- Slim curved arms with "Diff" logo
Style Number/Barcode: 07008-000142
Category Name: Vacation Looks
Price: $98.00
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetly Calculated Lace Trim Mini Dress
A little romance, a little edge. This halter mini dress hugs through the bodice, flares into an easy A-line shape, and finishes with lace trim that makes it feel styled even before you add heels.
Fit & Features
- Mesh-lined fabric, lace trim
- Halter neckline
- Partial open back
- Bodycon A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000828
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Golden Glow Strapless Maxi Dress
Serving sunkissed confidence with every step. The strapless lace maxi dress contours through the bodice, highlights the neckline with hardware detail, and falls into a sleek, elongating shape that feels equal parts elevated and effortless.
Fit & Features
- Striped design, lace-lined fabric
- Strapless sweetheart neckline, hardware insert, non-slip grip lining
- Form-hugging
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000425
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Floral Confidence Halter Crop Top
It’s the kind of top that makes sunset cocktails turn into dinners with a view. The floral cowl halter crop top features a fluid drape, statement orchid accent, and tie-back halter neckline that feels flirty, elevated, and ready for warm nights out.
Shop The Matching Skirt: Floral Confidence Maxi Skirt
Fit & Features
- Floral pattern, mesh lined fabric
- Orchid inset, halter cowl neckline, tie straps
- Open back design
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000468
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BANANA
Available Size: S, M, L
Product Badge:- Part of a Set
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Delicate and Daring Strappy Crop Top
This beaded hanky hem top contours through the bodice, dips into a V-neckline, and ties across the open back for a barely-there finish that pairs perfectly with tailored pants or a sleek mini skirt.
Fit & Features
- Mesh-lined fabric with beaded detailing
- V-neckline with slim adjustable straps
- Fitted bodice with hanky hem
- Open back with adjustable tie closure
- Runs true to size
Style Number/Barcode: 06001-000486
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Floral Confidence Maxi Skirt
It’s the kind of skirt that makes sunset cocktails turn into dinners with a view. The floral maxi skirt features a fluid drape, statement silhouette, and flared hem that feels flirty, elevated, and ready for warm nights out.
Shop The Matching Top: Floral Confidence Halter Crop Top
Fit & Features
- Tropical statement floral print
- Mesh fabric with smooth knit lining
- Mid-rise waist
- Curve-hugging
- Maxi flared hem
- Runs true to size
Style Number/Barcode: 06501-000116
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BANANA
Available Size: S, M, L
Product Badge:- Part of a Set
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Bold Allure O-Ring Cutout Bodycon Mini Dress
This is the one you wear when subtle just is not the plan. This cutout bodycon mini dress sculpts with high-stretch textured knit, while the plunging halter neckline and metal O-ring details serve just enough allure for late nights and last-minute plans.
Fit & Features
- Textured knit fabric, high stretch
- Sleeveless plunging scoop neckline
- Cutouts with metal O-ring accents
- Halter strap, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000298
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BROWN, CHARTREUSE
Available Size: XS, S, M, L
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Sunset Siren Cutout Bodycon Mini Dress
Serving sunkissed goddess with zero effort. This cutout bodycon mini dress hugs in all the right places, with sun-shaped hardware that turns a simple night out into a full-style statement.
Fit & Features
- Textured knit fabric, high stretch
- Strapless sweetheart neckline
- Dual cutouts at the bodice
- Metal sun-shaped hardware accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001140
Category Name: Vacation Looks
Price: $35.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Petals On Repeat Floral Tube Top
This is what you wear when the group chat says, “dress cute.” The floral tube top hugs in all the right places and gives you that effortless, vacation-coded look without overthinking it.
Shop The Matching Skirt: Floral Confidence Maxi Skirt
Fit & Features
- Tropical statement floral print
- Mesh fabric with smooth knit lining
- Strapless neckline, non-slip grip lining
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000475
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BANANA
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Nicki Beaded Fringe Mermaid Formal Dress
Special Occasion
Designed for the kind of entrance that feels quietly iconic, the Nicki beaded mesh mermaid silhouette moves with intention and undeniable polish. A beaded triangle bust with fringe and a high front slit brings just enough drama to a look made for weddings, galas, and unforgettable nights.
Fit & Features
- Smooth knit-lined fabric, moderate stretch
- Beaded triangle bust silhouette with fringe
- Halter spaghetti strap
- Back zipper and hook-eye closure
- Mermaid silhouette with high front slit
- Floor-length hem
- Runs true to size
Where to Wear:
Prom, big birthday events, fashion-forward soirees, upscale cocktail parties, glamorous occasions, red-carpet events
Style Number/Barcode: 05002-001093
Category Name: Vacation Looks
Price: $99.90
Availability: In Stock
Available Color: WINE, GOLD
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Addison Animal Print Formal Dress
Special Occasion
A little daring, a lot refined, the Addison dresswas made for the kind of entrance that lingers long after you’ve crossed the room. Designed in striking animal print with a sculpted mermaid fit, this gown features a cutout bodice with a hoop insert and an open strappy back finished with beaded tie-back straps for a look that feels equal parts polished and unforgettable.
Fit & Features
- Animal print mesh fabric, knit lining
- Plunging neckline with cutout bodice, padded bra cups
- Hoop insert detail at the center front
- Open strappy back with beaded tie-back straps
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Destination weddings, resort dinners, vacation, honeymoons, date night, cocktail parties, birthday parties, bachelorettes
Style Number/Barcode: 05002-000713
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Sheer Confidence Ruffled Mesh Sarong
This is the layer that turns a simple bikini into a full look. This ruffled mesh sarong hugs in all the right places with a flirty tie-waist and sheer finish that was made for beach clubs, pool parties, and spontaneous golden hour plans.
Fit & Features
- Sheer mesh fabric with high stretch
- Tie-waist design
- Long ruffled accents
- Mini-length ruffled hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 07105-000036
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: BLACK, MINT
Available Size: S/M, L/XL