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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Day To Night Halter Neck Top
Last-minute plans, handled. This halter neck top hugs just right with a smooth knit feel and a subtle cutout that keeps things sultry with your favorite bottoms.
Fit & Features
- Smooth knit stretch fabric
- Square cutout halter high neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000533
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Effortless Finish Strappy Sandals
These strappy sandals keep it minimal with a sleek silhouette and a hint of hardware that pulls your whole look together. Perfect for everyday styling, vacations, or weekend looks.
Fit & Features
- Square toe
- Strappy design with hardware detail
- Flat sole, luxe fit cushioned insole
- Faux leather material
- Slip-on style
- Runs true to size
Style Number/Barcode: 07404-000068
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: BROWN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Effortless Charm Babydoll Halter Top
Cute plans start here—this top just gets it. A babydoll halter top with a floaty fit that feels light, easy, and made for warm days or dressed-up nights.
Fit & Features
- Sheer textured woven fabric with woven lining, no stretch
- Sleeveless sweetheart neckline, no-slip strip, ruched bust
- Halter tie-back spaghetti straps
- Partial stretchy smocked back
- Babydoll crop-length silhouette, flowy fit, asymmetric hem
- Runs true to size
Style Number/Barcode: 06003-000296
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Flirt Factor Floral Mesh Maxi Dress
When the invite says dress up, this is already in your hands. This flirty floral mesh maxi dress brings a sleek, curve-hugging fit with lightweight stretch that feels as good as it looks all night.
Fit & Features
- Sheer mesh fabric, full-length knit lining, high stretch
- Large floral print
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-001135
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Island Heat Mesh Maxi Dress
Booked, busy, and dressed like it. This tropical floral maxi dress is form-hugging with a high side slit that brings just enough drama for your next getaway or sunset dinner.
Fit & Features
- Tropical floral print, mesh fabric, brushed knit lining
- Strapless tube neckline, non-slip grip lining
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000626
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Poolside Crush Gingham Bikini Bottoms
This gingham triangle bikini bottom keeps it classic with a cheeky fit and adjustable ties to get a perfect fit.
Shop Matching Top: Poolside Crush Gingham Bikini Top
Fit & Features
- Gingham print, lined fabric
- Low-rise waist
- Adjustable side ties
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000056
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L
Product Badge:- Part of a Set
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Poolside Crush Gingham Bikini Top
This gingham triangle bikini top keeps it classic with a barely-there fit and adjustable back tie to get a perfect fit.
Shop Matching Bottoms: Poolside Crush Gingham Bikini Bottoms
Fit & Features
- Gingham print, lined fabric
- Triangle cups
- Adjustable spaghetti straps
- Adjustable back tie
- Runs true to size
Style Number/Barcode: 07104-000036
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L
Product Badge:- Part of a Set
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Flirty Vibe Butterfly Print Mesh Halter Top
A little flirty, a little hard to ignore—exactly your vibe. This butterfly print mesh halter top drapes with a soft cowl neckline and features O-ring accents and an open back for a fab vibe. Style with the matching maxi skirt.
Shop Matching Bottoms: Flirty Vibe Butterfly Print Mesh Maxi Skirt
Fit & Features
- Sheer mesh fabric with brushed knit lining, high stretch
- Butterfly print
- Sleeveless plunging cowl neckline
- Halter tie-back spaghetti straps, metal O-ring hardware accents
- Open back, lower tie-back straps
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000512
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sunset Muse Ombre Mesh Cutout Maxi Dress
Serving curves, movement, and just enough drama. This ombre mesh cutout maxi dress hugs in all the right places with a fluid drape that feels effortless but looks unforgettable.
Fit & Features
- Ombre sheer mesh fabric with full-length knit lining, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Halter tie-back straps
- Asymmetric waist cutouts leading to an open back
- Maxi-length hem, floor-length center sash accent
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-001168
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Flirty Vibe Butterfly Print Mesh Maxi Skirt
A little flirty, a little hard to ignore—exactly your vibe. This butterfly print mesh maxi skirt features a high-cut front slit, asymmetric hem, and flowy silhouette for a fab vibe. Style with the matching halter top.
Shop Matching Top: Flirty Vibe Butterfly Print Mesh Halter Top
Fit & Features
- Mesh fabric with high stretch
- Butterfly print
- High-rise waist
- High-cut front slit
- Maxi-length asymmetric hem
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-000129
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Daytime Darling Eyelet Mini Dress
Caught the vibe and didn’t think twice. This puff sleeve eyelet mini dress hugs just right with a flirty tie front—perfect for brunch dates, daytime plans, and those “I look cute today” moments.
Fit & Features
- Eyelet knit fabric
- Sweetheart neckline, tie bust keyhole cutout accent
- Puff short sleeves
- Princess seam detailing
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000462
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Beach Plans Side Tie Bikini Bottoms
Booked the trip or just planning a beach day—either way, you’re ready. These bikini bottoms sit just right with adjustable ties for a perfect fit and confident feel from poolside lounging to ocean dips.
Shop The Matching Bikini Top: Beach Plans Triangle Bikini Top
Fit & Features
- Sleek knit-lined fabric
- Low-rise waist, adjustable side ties
- Cheeky coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000042
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: RED, ROYAL
Available Size: S, M, L
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Beach Plans Triangle Bikini Top
Booked the trip or just planning a beach day—either way, you’re ready. This bikini top offers a perfect fit with adjustable ties and a confident feel from poolside lounging to ocean dips.
Shop The Matching Bikini Bottoms: Beach Plans Side Tie Bikini Bottoms
Fit & Features
- Sleek knit-lined fabric
- Triangle cups with a hardware insert
- Adjustable back ties
- Runs true to size
Style Number/Barcode: 07104-000029
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: RED, ROYAL
Available Size: S, M, L
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Luxe Nights Halter Mini Dress
This is the dress you wear when subtle isn’t the plan. This halter mini dress sculpts with a ruched design, a plunging neckline, and statement hardware that pulls it all together—perfect for nights out or that last-minute RSVP.
Fit & Features
- Smooth knit fabric with moderate stretch
- Plunge halter neckline, hardware inset
- Open back design
- Ruched bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05103-000711
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Alaiya Floral Chiffon Ruffle A-Line Dress
Special Occasion
Light, airy, and made for your most picturesque plans, the Alaiya floral chiffon A-line dress moves like a breeze with every step. Designed with soft ruffles, a romantic halter neckline, and a lace-up back detail, it’s the kind of dress that turns a simple entrance into a moment.
Fit & Features
- Floral-printed chiffon fabric with full-length lining
- Sleeveless sweetheart neckline, padded bust, ruched detailing
- Halter tie-back straps
- Open back, lower lace-up back design with tie closure, lower back zipper with hook-eye closure
- Floor-length A-line silhouette, flowy ruffled accents
- Runs true to size
Where to Wear:
Birthday celebrations, bridal showers, honeymoons, vacations, garden parties, and dressed-up dinners.
Style Number/Barcode: 05002-001450
Category Name: Vacation Looks
Price: $129.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Hot Plans Tropical Tube Mini Dress
Booked, busy, and dressed for it. This tropical floral mini dress hugs in all the right places with a sleek strapless fit—made for vacations, beach weekends, and last-minute plans that turn into everything.
Fit & Features
- Tropical floral print, stretchy knit fabric
- Tube strapless neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000547
Category Name: Vacation Looks
Price: $35.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Major Fling Flutter Sleeve Maxi Dress
Fling into the spring season in this maxi dress that has an effortlessly breezy feel, while the V-neck and cutout back give it that easy, getaway-ready charm.
Fit & Features
- Airy cotton fabric, woven lining
- Flutter short sleeves
- V-neckline
- Cutout back
- Ruffled tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000748
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Dinner Plans Sleeveless Maxi Dress
This crewneck maxi dress hugs your shape with a soft shimmer finish and adjustable side ties atop flirty slits, making it your go-to for dinner plans, vacations, or beach nights.
Fit & Features
- Lurex knit fabric
- Sleeveless crewneck
- Adjustable side ties and high slits
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05103-000854
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: GOLD
Available Size: XS, S, M, L
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Pretty In Motion Halter Mini Dress
Caught a vibe and dressed for it. This halter mini dress cinches at the waist with a flowy A-line skirt that moves with you—perfect for weekends that start with plans and end wherever.
Fit & Features
- Smooth stretch material
- Halter neckline with open back, tie straps
- Ruched waist detail
- A-line mini silhouette with pleated skirt
- Runs true to size
Style Number/Barcode: 05102-000358
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: ROYAL
Available Size: XS, S, M, L
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Tropic Heat Floral Mini Dress
Serving vacation energy even if you’re not booked yet. This floral mesh dress contours your shape with a plunging neckline and open back that does all the talking.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000625
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Laidback Classic Denim Shorts
The pair you’ll keep reaching for without thinking twice. These high-rise denim shorts keep it simple with a flattering fit that works with literally everything in your closet.
Fit & Features
- Denim fabric, no stretch
- High-rise waistband
- Frayed hem trim
- Form-hugging fit
- Front button and hidden zipper closure, belt loop accents
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-000208
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: MED, DENIM
Available Size: 0, 1, 3, 5, 7, 9, 11, 13
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Easy Going Distressed Denim Shorts
Your throw-on-and-go pair of denim shorts! These distressed denim shorts sit just right, with a laid-back fit that works from coffee runs to sunny-day plans.
Fit & Features
- Denim fabric, minimal stretch
- Mid-rise waistband
- Distressed accents
- Cutoff hem
- Front button and hidden zipper closure, belt loop accents
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-000209
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: MED, DENIM
Available Size: 0, 1, 3, 5, 7, 9, 11, 13
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Getaway Mode Tropical Print Wide-Leg Pants
Serving effortless getaway vibes—these tropical print wide-leg pants are your go-to for sunny plans and spontaneous outfit pics. Lightweight with a chic, relaxed fit, they're made for warm days that turn into late nights. Style with the matching tie-front top.
Shop Matching Top: Getaway Mode Tropical Print Tie-Front Top
Fit & Features
- Smooth knit fabric, high stretch
- Tropical print
- High-rise waist
- Hip-hugging fit
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000084
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Getaway Mode Tropical Print Tie-Front Top
Serving effortless getaway vibes—this tropical print tie-front top is your go-to for sunny plans and spontaneous outfit pics. Lightweight with a chic cropped fit, it’s made for warm days that turn into late nights. Style with the matching wide-leg pants.
Shop Matching Bottoms: Getaway Mode Tropical Print Wide-Leg Pants
Fit & Features
- Smooth knit fabric, high stretch
- Tropical print
- Short flowy sleeves
- V-neckline, tie-front closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-000090
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Part of a Set