Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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Vacation Looks
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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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Casually Cool Slit Maxi Dress
Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.
Fit & Features
- Sleeveless scoop neck
- Bungee spaghetti straps
- Form-hugging
- High-cut side slit
- Maxi-length hem
- Rib-knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4883
Category Name: Vacation Looks
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Darling Woven Drop-Waist Skater Dress
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace.
Fit & Features
- Woven fabric with lace trim woven lining
- Sweetheart neckline, ruched bust, adjustable tie-front
- Tank straps, lace-up back design
- Back zipper and hook-eye closure
- Asymmetric drop-waist, pleated side panels
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3378
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meet In The Hamptons Linen Wide Leg Pants
These linen wide-leg pants have a Hampton's getaway written all over it! Look cute strolling through the town in these pants featuring a flattering high-rise waist and a hidden back zipper closure. Style with the matching top and a dainty necklace to complete the chic look!
Shop Matching Top: Meet In The Hamptons Linen Crop Top
Fit & Features
- High-rise waist
- Hidden back zipper closure
- Wide-leg silhouette
- Lined linen fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0723
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Coastal Crush Starfish And Pearl Drop Earrings
Giving mermaid-core in the cutest way possible. These starfish drop earrings with faux pearls are your new fave vacation plus-one—just add salty waves and a sundress.
Fit & Features
- Textured metal starfish stud detail
- Faux pearl drop with glossy finish
- Lightweight dangle silhouette
- Push-back post closure
Earrings are final sale and may not be returned or exchangedStyle Number/Barcode: 07001-000127
Category Name: Vacation Looks
Price: $7.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sunlight Dream Floral Paisley Silk Scarf
Create a dreamy daytime vibe with this silk scarf featuring a blooming floral paisley print and multiple styling options! Complete the look with a basic bodysuit, jeans, and a coffee in hand to stroll the streets of a cute downtown area.
Fit & Features
- Floral paisley print
- Silky material
- Multiple styling options
Style Number/Barcode: 07305-0450
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cuddle Time Chenille Crop Cardigan
Wrap yourself in this chenille crop cardigan for a cute and cuddly vibe! The sweater features long sleeves, a ribbed open-front design, and a cropped hem on ultra-soft and cozy chenille knit fabric. Complete the look in the matching cozy pajama top and bottoms for a chill night in!
Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top
Shop Matching Pajama Bottoms: Feeling The Vibe High-Rise Chenille Joggers
Fit & Features
- Long sleeves
- Ribbed open-front design
- Cropped hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0946
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Arrived In Style Chiffon Sheer Kimono
Arrive wherever you're headed in this stylish chiffon sheer kimono to elevate your outfit! It features breezy short sleeves, an open front design, side slit accents, and a flowy mid-calf length hem. Layer over a crop top, shorts, and sassy lace-up heels to complete your look!
Fit & Features
- Breezy short sleeves
- Open front design
- Side slit accents
- Flowy mid-calf length hem
- Sheer, airy chiffon fabric
- Runs true to size
Style Number/Barcode: 06204-1333
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Savor The Moment Halter Cutout Maxi Dress
Step into the spotlight in this halter maxi dress on vacation or for some summer fun! Featuring a striking halter neckline adorned with elegant hardware and a shimmering stone insert, this bodycon dress offers a bold cutout design that highlights your figure.
Fit & Features
- Smooth knit stretchy fabric
- Halter neckline with tie closure
- Hardware and stone insert
- Cutout accents
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000030
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Smoke And Mirrors Square Sunglasses
No matter your mood, these square sunglasses are perfect for slipping on when you can't even! They feature a sleek metal frame with cool, smokey pink-tinted lenses and rubber nose supports. Complete the look in a flirty printed sundress for a day out.
Fit & Features
- Square sleek metal frame
- Rubber nose supports
- Smokey pink tinted lenses
Style Number/Barcode: 07008-1006
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Babe Slip-On Wedge Sandals
For strolls along the coast or any weekend adventure, these slip-on wedge sandals provide comfort and style! They feature a square toe, a wide strap, and a platform sole of faux leather material. Complete the look with cute sunglasses.
Fit & Features
- Square toe, wide strap
- Platform sole
- Wedge style
- Slip-on and off styling
- Faux leather material, cushioned insole
- Runs true to size
Style Number/Barcode: 07404-1093
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Scandal Tropical Cutout Maxi Dress
Booked the trip? Now bring the drama in this tropical maxi dress! With metal hardware and skin-baring cutouts, this maxi is not for blending in—it's bold, body-hugging, and built for after-hours.
Fit & Features
- Tropical print, mesh fabric, smooth stretchy knit lining
- Halter neckline with hardware accents, spaghetti strap tie
- Bandeau-style cutout bodice with center metal U-ring
- Ruched high waist with hardware accent
- High front slit on a body-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000032
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Mode Ruched Bikini Top
Activate sunny mode with this hot bikini top featuring a ruched bust, curved underwire for structure, and adjustable spaghetti straps. Style with the matching bikini bottoms to be sitting pretty poolside!
Shop Matching Bottoms: Sunny Mode V-Cut Bikini Bottoms
Fit & Features
- Nylon-blend fabric, high stretch
- Lined cups, curved underwire, no padding
- Ruched bust
- Adjustable spaghetti straps
- Back strap with hook and bar closure
- Runs true to size
Style Number/Barcode: 07104-000005
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Poolside Paradise Floral Triangle Bikini Top
So pretty and made for tanning, this floral bikini top offers flattering triangle-shaped cups and dual spaghetti strap ties that let you customize the style! Pair with the matching bikini bottoms.
Shop Matching Bottoms: Poolside Paradise Floral Scrunch Bikini Bottoms
Fit & Features
- Floral print, stretchy knit fabric
- V-shaped low-rise waist
- Scrunched thong back coverage
- Runs true to size
Style Number/Barcode: 07104-000007
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sangria Please Striped Halter Top
Can't you imagine wearing this striped halter top while sipping on a sangria? Set the tone this vacay-ready crop top featuring a sleeveless, halter neck, tie-closure, striped pattern, and a smocked back. Complete the look in the matching bottoms.
Shop The Matching Bottoms: Sangria Please Striped Wide Leg Pants
Fit & Features
- Sleeveless, halter neck, tie-closure
- Cropped hem
- Smocked back
- Striped pattern
- Gauze woven fabric, no stretch, fits true to size
Style Number/Barcode: 06003-1568
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wandering Bliss Halter Crochet Jumpsuit
Wander in bliss looking so boho in this sleeveless jumpsuit perfect for a music festival or summer vacation! It features a halter V-neckline with tie closure, an open back, a crochet waist, and a flowy wide-leg silhouette on gauze-woven fabric. Complete the look n espadrille wedges.
Fit & Features
- Sleeveless halter V-neckline, tie closure
- Open back
- Crochet waist
- Wide-leg silhouette
- Gauze woven fabric
- No stretch
- Runs true to size
Style Number/Barcode: 06302-0724
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Bliss Faux Fur Bucket Hat
Fit & Features
- Oversized bucket design
- Faux fur fabrication
Style Number/Barcode: 07302-1734
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Party Hour Rhinestone Beer And Lime Earrings
Dive into fun with these rhinestone beer and lime earrings. Featuring a lime slice post and sparkling beer bottle design, these earrings are your perfect party pals. Cheers to style!
Fit & Features
- Lime slice post
- Hanging beer bottle design
- Mini rhinestone embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2321
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Aura Floral Print Strapless Crop Top
Nail your look with cute jeans and this floral print strapless crop top. Featuring a V-cut insert and ruching, this flirty piece hugs your curves and brings all the vibes.
Fit & Features
- Lined knit fabric with plenty of stretch
- Large floral print
- Strapless neckline with V-cut insert
- Ruching
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-5552
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coastal Chic Starfish Dangle Earrings
Fit & Features
- Dangle design
- Textured starfish charm
- Fish hook closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2329
Category Name: Vacation Looks
Price: $3.97 $7.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutely Charming One-Shoulder Crop Top
Go ahead and strut your cute and charming self in this sleeveless crop top to elevate your basics collection! It boasts a one-shoulder neckline with a cinch detail, and a fitted crop hem on stretchy rib knit fabric. Complete the look in a denim midi skirt and sandals!
Fit & Features
- Stretchy rib knit fabric
- One-shoulder neckline
- Tank strap with cinch detail
- Fitted crop length hem
- Runs true to size
Style Number/Barcode: 06002-1909
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fierce Allure Leopard Print Mesh Maxi Dress
Flaunt a fierce allure in this curve-hugging leopard print maxi dress! The airy sheer mesh fabric lined with knit offers plenty of stretch and showcases a leopard print pattern for a sultry-chic vibe. The long dress features a sleeveless V-neckline, spaghetti straps, a form-fitting silhouette to accent your gorgeous curves, and a maxi-length hem. Style with strappy mules for a rooftop happy hour.
Fit & Features
- Leopard print
- Sheer mesh fabric with knit lining, plenty of stretch
- V-neckline
- Spaghetti straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-3328
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Arm Candy Stacking Bangle Bracelet Set
Because one bracelet is never enough. This stacking bangle set mixes bold and sleek textures so you can layer up for that effortlessly luxe vibe.
Fit & Features
- Mixed metal
- Assorted bangle silhouettes
- Smooth, textured, and braided designs
Style Number/Barcode: 07003-000079
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top
Wildly sultry is exactly how you'll look in this leopard rose mesh crop top on a night out! The flared long sleeves and V-neckline with tie closure give a playful touch, while the center slit adds a touch of allure. The cropped length and striking leopard rose print make this top a must-have for any bold fashionista. Complete the look with the matching skirt.
Shop Matching Bottoms: Wildy Sultry High Rise Leopard Floral Maxi Skirt
Fit & Features
- Leopard rose print, sheer mesh fabric, moderate stretch
- Flared long sleeves
- V-neckline
- Tie-front closure and center slit
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-0472
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wildy Sultry High Rise Leopard Floral Maxi Skirt
Wildly sultry is exactly how you'll look in this leopard rose mesh maxi skirt on a night out! The skirt boasts a flattering high-rise waist complimented by a bodycon silhouette that accentuates your curves along the midi-length hem. Complete the look with the matching top.
Shop Matching Top: Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top
Fit & Features
- Leopard floral print, mesh fabric lined with stretchy knit
- High-rise waist
- Hip-hugging fit
- Maxi-length
- Runs true to size
Style Number/Barcode: 06501-1052
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free