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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Tropic Temptation Mesh Mini Dress
This floral and animal print mesh mini dress brings all the playful drama with a sweetheart neckline, flirty ruffle tiers, and cascading side sash details made for beach clubs, birthday trips, and late-night dancing.
Fit & Features
- Floral and animal print, mesh-lined fabric
- Strapless cutout neckline
- Ruched bodycon silhouette
- Side ruffled drapes
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000745
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: MULTI, BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Love At First Text Lace Top
The kind of top that changes the whole outfit. With its delicate lace, plunge neckline, and barely there feel, this flyaway halter is made for concerts and spontaneous plans.
Fit & Features
- Lace woven fabric, lined
- Plunge halter neckline, bar accent, tie straps
- Open back
- Ruffled split crop hem
- Runs true to size
Style Number/Barcode: 06003-000332
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
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Tropic Crush Flower Hair Clip Set
A little flower moment goes a long way. This vibrant three-piece hair clip set brings instant vacation vibes to any look, whether you're heading to brunch, a beach day, or just trying to make a simple hairstyle look cute.
Fit & Features
- Three-piece hair clip set
- Tropical flowers
- Metal clip closure
Style Number/Barcode: 07006-000158
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Jungle After Hours Ruffle Romper
This halter romper brings together bold tropical blooms, a striking zebra-inspired print, and cascading ruffle details for a look that was made to turn heads. With its plunging halter neckline, open back, and built-in shorts underneath, it's perfect for nights out.
Fit & Features
- Floral, zebra print, mesh fabric, knit lining
- Cowl halter neckline, tie straps
- Open back
- Form-hugging fit
- Layered ruffle mini-length hem, side cascading ruffles
- Built-in knit shorts lining
- Runs true to size
Style Number/Barcode: 06503-000320
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: ZEBRA
Available Size: XS, S, M
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Paradise Found Floral Mini Dress
Found it: the dress that makes every plan feel like a getaway. With a dreamy tropical print, a plunging halter neckline, and playful tiered ruffles, this dress was made for beach clubs, sunset cocktails, and dinner with a show.
Fit & Features
- Tropical floral print, mesh-lined fabric, built-in panty lining
- Halter plunge neckline, tie straps, hardware accent
- Open back
- Form-hugging fit
- Layered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000945
Category Name: Vacation Looks
Price: $19.97 $40.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Sale
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Warm Breeze One Shoulder Poncho
The kind of striped poncho that makes even the simplest denim look styled. Designed with a relaxed one-shoulder silhouette, airy drape, and subtle lurex shimmer woven throughout, this statement poncho brings effortless vacation vibes wherever you're headed.
Fit & Features
- Striped pattern
- Lurex shimmer knit fabric
- One-shoulder neckline
- Relaxed poncho silhouette
- Runs true to size
Style Number/Barcode: 06202-000114
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: GOLD
Available Size: XS/S, M/L
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Seashell Dreams Striped Mini Dress
The kind of dress that makes packing for vacation feel easy. With a shimmering striped knit, plunging halter neckline, and open-back silhouette, it brings effortless beach club energy whether you're heading to dinner by the water or chasing golden hour plans.
Fit & Features
- Striped pattern, lurex knit fabric, sewn-in knit lining
- Halter neckline, tie straps
- Open back
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001253
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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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 with lining
- 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
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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: Out of Stock
Product Badge:- Ships Free
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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: Out of Stock
Product Badge:- Ships Free
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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:- Back In Stock
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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: Out of Stock
Product Badge:- Ships Free
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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
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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: S, M, L
Product Badge:- Part of a Set
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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:- Back In Stock
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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: 7.5, 8.5, 9, 10, 11
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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: 07008-000154
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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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: Out of Stock
Product Badge:- Ships Free
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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
- 4.5" 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: 8.5, 9, 10, 11
Product Badge:- Best Seller
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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: 8.5
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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: Out of Stock
Product Badge:- Ships Free
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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