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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Vacay Romance Floral Maxi Dress
This is the dress that turns dinner plans into an occasion. Featuring a draped cowl neckline, open back, and oversized florals, it hugs in all the right places while serving effortless looks on vacations, weekend getaways, or date nights.
Fit & Features
- Floral tropical print, knit stretchy fabric
- Cowl halter neckline, tie straps
- Open back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001148
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Gianna Striped Linen A-Line Formal Dress
Special Occasions
Effortlessly striking and made for sun-drenched celebrations, the Gianna dress brings together a softly textured striped linen fabric with a modern asymmetrical silhouette. The ruched bodice, side cutout detail, and flowing a-line skirt create beautiful movement, while the open tie-back design adds an unexpected finishing touch.
Fit & Features
- Striped pattern, subtle metallic threads, linen-blend fabric, sewn-in bodice lining
- Asymmetrical neckline, spaghetti straps
- Open tie-back detail, side zipper and hook-eye closure
- Side cutout, ruched bodice accent
- A-line silhouette, high side slit
- Floor-length hem
- Runs true to size
Where to Wear:
Outdoor weddings, vacations, honeymoons, resorts, birthday brunches, cocktail events, engagement parties, summer dinner parties, wineries
Style Number/Barcode: 05002-001567
Category Name: Vacation Looks
Price: $99.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Ailith Metallic Striped Formal Dress
Special Occasion
Like a sunset slipping into evening, the Ailith metallic knit column gown catches the light with every step. The softly draped neckline and open cowl back with delicate tie detailing create an effortlessly polished silhouette that feels made for formal celebrations and unforgettable entrances.
Fit & Features
- Metallic striped knit fabric, smooth knit lining
- Cowl neckline
- Adjustable spaghetti straps
- Open tie-back with draped accent
- Column floor-length silhouette
- Runs true to size
Where to Wear:
Outdoor weddings, galas, honeymoons, vacations, resorts, engagement parties, rehearsal dinners, cocktail events, formal milestone celebrations, date nights
Style Number/Barcode: 05002-001738
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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City Escape Aviator Sunglasses
These aviator sunglasses are the finishing touch for poolside selfies, coffee runs, and pretending you’re off the grid for the weekend.
Fit & Features
- Aviator silhouette
- Clear tinted lenses
- Lightweight frame
- 100% UV protection
Style Number/Barcode: 07008-000180
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: RED
Available Size: NS
Product Badge:- New Arrival
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Resort Vacay Shell Chandelier Earrings
The kind of earrings that make every outfit feel a little more expensive. These cascading shell chandelier earrings were made for vacation dinners, messy buns, and compliments from strangers.
Fit & Features
- Round sheel cascading design
- Chandelier silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000350
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Moonlit Escape Chiffon Poncho
This sheer chiffon poncho drapes with an easy off-the-shoulder feel, while delicate lace trim adds just the right amount of detail. Toss it over swimwear, pair it with denim, or wear it whenever your outfit needs that extra little something.
Fit & Features
- Sheer chiffon fabric
- Asymmetrical one-shoulder neckline
- Relaxed poncho silhouette
- Lace trim hem
- Runs true to size
Style Number/Barcode: 06204-000173
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: BLACK
Available Size: XS/S, M/L
Product Badge:- New Arrival
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Weekend Breeze Crop Top
This top was made for sunny forecasts and spontaneous plans. The airy gauze fabric, soft hue, and trendy crop length make it look effortless.
Shop Matching Bottoms: Weekend Breeze Maxi Skirt
Fit & Features
- Gauze woven fabric
- Square neckline
- Adjustable spaghetti straps
- Cinched crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000352
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Everyday Luxe Square Sunglasses
These oversized square sunglasses feature warm gradient lenses, sleek gold-tone details, and a polished silhouette that feels equally at home on vacation, at brunch, or running errands with an iced coffee in hand.
Fit & Features
- Oversized square frames
- Rubber nose supports
- Sleek metal arms with plastic trim
- Tinted lenses
Style Number/Barcode: 07008-000137
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
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Bright Side Bracelet Set
This chunky bangle bracelet set mixes translucent and vibrant colorways for an easy statement that pairs perfectly with everything from vacation looks to casual denim days.
Fit & Features
- Two pack bracelet set
- Colored resin material
- Chunky silhouette
Style Number/Barcode: 07003-000242
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
Product Badge:- New Arrival
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Wild Side Zebra Print Tie-Front Top
Serving confidence with a little bit of chaos. This zebra print mesh tie-front top brings all the drama with a deep neckline, flowy flare sleeves, and an ultra-cropped fit made for statement-making plans. Style with the matching maxi skirt.
Shop Matching Bottoms: Wild Side Zebra Print High-Slit Maxi Skirt
Fit & Features
- Zebra print sheer mesh fabric, high stretch
- Deep V-neckline
- Tie-front design
- Long flowy flare sleeves
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06202-000116
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: ZEBRA
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Clear Choice Jelly Thong Strap Kitten Heels
Minimal effort, maximum outfit payoff. These jelly thong strap kitten heels bring a barely-there look that pairs perfectly with everything from denim and cargos to your favorite vacation-ready dresses.
Fit & Features
- Kitten heel
- Open square-shaped toe
- Clear jelly thong straps, toe strap
- Open back, on-and-off styling
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07401-000649
Category Name: Vacation Looks
Price: $30.90
Availability: In Stock
Available Color: NATURAL
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Effortless Days Sheer Chiffon Poncho
Floaty, effortless, and impossible to overlook. This sheer chiffon poncho drapes with an airy relaxed fit that instantly elevates everything from swimwear, mini skirts, and vacation-ready looks.
Fit & Features
- Sheer chiffon woven fabric, no stretch
- Boat neckline
- Long flowy sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-000174
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: IVORY
Available Size: XS/S, M/L
Product Badge:- New Arrival
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Plans Confirmed Strappy Wedges
The kind of wedges that make every outfit feel cuter. With strappy details and a trendy cork platform sole, they're ready for everything from brunch reservations to wedding guest weekends.
Fit & Features
- 5" Wedge heel
- Almond toe
- Strappy design
- Adjustable ankle strap with buckle closure
- Cork platform sole
- Runs true to size
Style Number/Barcode: 07406-000062
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: WHITE, GOLD
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10, 11
Product Badge:- New Arrival
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Sunshine State Chiffon Babydoll Top
The kind of top that makes saying yes to plans way too easy. This chiffon babydoll top features a plunging halter neckline, flowy pleated silhouette, and open back detail made for warm nights, weekend getaways, and last-minute plans.
Fit & Features
- Chiffon fabric, knit lining
- Halter plunge neckline, tie straps
- Open back with tie
- Flouncy ruffled babydoll silhouette
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000398
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Saltwater Chic Crochet Cardigan
The cardigan that makes every swim look styled. Designed with an airy open-knit crochet, tie-front details, and shell-trimmed bell sleeves that catch the light with every step, this duster was made for pool parties, vacations, and weekend escapes.
Fit & Features
- Sheer crochet fabric
- Long bell sleeves with shell embellished trim
- Dual tie-front closures
- Open front design
- Long-length hem
- Runs true to size
Style Number/Barcode: 06204-000153
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Brunch Bound Espadrille Wedges
Elevating every outfit without even trying. These espadrille wedges pair braided textures with an easy platform silhouette, making them the pair you'll reach for from brunch dates to vacation plans.
Fit & Features
- Espadrille wedge heel
- Platform sole
- Open round toe
- Espadrille straps
- Dual straps across the foot, adjustable ankle strap with buckle closure
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-000070
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: 6, 7, 8, 9, 10
Product Badge:- New Arrival
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Runway Route Square Sunglasses
These rimless square sunglasses bring a sleek, trend-forward finish to every outfit, whether you're heading to work or weekend plans. These sunglasses make every car ride fashionable.
Fit & Features
- Lightweight square frame silhouette
- Sleek bar trim
- Rubber nose supports
- Metal arms with plastic trim
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000153
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: ROSE, GOLD
Available Size: NS
Product Badge:- New Arrival
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Mermaid Hour Lurex Poncho
Caught the light from every angle? Exactly the plan. This airy lurex poncho drapes effortlessly over swimwear, tops, and going-out looks, adding just the right amount of shimmer.
Fit & Features
- Shimmer knit lurex fabric, sheer design
- Off-shoulder neckline
- Flowy fit
- Asymmetrical hem
- Runs true to size
Style Number/Barcode: 06202-000105
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: TEAL
Available Size: XS/S, M/L
Product Badge:- New Arrival
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Chic On Arrival Metallic Espadrille Wedges
These metallic espadrille wedges pair a leg-lengthening platform with sleek straps, making them an easy chic pick for weddings, vacations, rooftop dinners, and every RSVP in between.
Fit & Features
- Espadrille wedge heel
- Open round toe
- Metallic faux leather straps
- Toe strap, adjustable ankle strap with buckle closure
- Metallic faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-000063
Category Name: Vacation Looks
Price: $40.90
Availability: In Stock
Available Color: GOLD
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10, 11
Product Badge:- New Arrival
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Weekend Away Bow Thong Sandals
Tiny bow details just make everything feel cuter. These faux leather sandals are the pair you pack for trips or any weekend plans.
Fit & Features
- Almond toe
- Thong strap with bow
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000077
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: WHITE
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Spritz O' Clock Kitten Striped Heels
The shoes that make every outfit look like it came with a boarding pass. With a woven raffia finish and an easy slip-on design, these mule heels are ready for dinners, brunch reservations, and every sunny plan in between.
Fit & Features
- Kitten stiletto heel
- Pointed toe
- Curved band
- Cushioned insole
- Striped pattern, rafia material
- Runs true to size
Style Number/Barcode: 07401-000746
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: MULTI
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Serving Looks Leopard Print Halter Top
Serving looks without saying a word. This leopard print halter top hugs in all the right places with a draped cowl neckline and open-back detail that was made for plans worth getting dressed up for. Pair with the matching mini skort.
Shop Matching Bottoms: Serving Looks Leopard Print Ruffle Mini Skort
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract leopard print
- Sleeveless cowl neckline, bar strap detail
- Halter strap, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000591
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sparkly Fave Rhinestone Floral Ruffle Romper
Straight to the favorites folder. This rhinestone floral ruffle romper pairs a plunging halter neckline with sparkling details and a flouncy layered hem that was made for birthday dinners, vacation nights, and every photo op in between.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless deep V-neckline, rhinestone floral embellishments
- Tie-back halter straps, partially open back
- Ruched drop waist design
- Tiered ruffled overlay with mini-length hem, A-line fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000321
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Weekend Breeze Maxi Skirt
This skirt was made for sunny forecasts and spontaneous plans. The airy gauze fabric, soft hue, and flirty high front slit make it look effortless.
Shop Matching Top: Weekend Breeze Crop Top
Fit & Features
- Gauze woven fabric
- High-rise waist
- Flowy tiered silhouette
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-000014
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- Part of a Set