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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Seraphina Convertible Formal Dress
Special Occasion
The Seraphine A-line gown pairs a dramatic convertible halter neckline with striking cutout details for a look that feels equal parts polished and daring. The flowing silhouette, open back, and adjustable ties create a custom feel that moves beautifully from cocktail hour to the last dance.
Fit & Features
- Smooth knit fabric, moderate stretch
- Convertible neckline, multiple ways to style
- Cutout accents
- Open tie-back detail
- High side slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, rehearsal dinners, engagement parties, formal milestone celebrations, black tie galas, special date nights, cocktail soirees, fancy birthdays, vacations, honeymoons
Style Number/Barcode: 05002-001662
Category Name: Vacation Looks
Price: $29.97 $59.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Caught In Lace Bodycon Mini Dress
Too dressed up to stay home anyway. This lace bodycon mini dress features a plunging neckline, ruffle trim, and an open back that makes every entrance feel slightly dramatic.
Fit & Features
- Delicate lace mesh fabric, knit lining
- Plunge ruffled trim neckline with strappy detail
- Sheer fitted long sleeves, ruffle cuffs
- Open back cutout design
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000846
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Sale
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Sonya Crochet A-Line Formal Dress
Special Occasion
Made for moonlit celebrations and unforgettable entrances, the Sonya chiffon A-line gown balances airy movement with intricate crochet detailing and a striking front cutout. The flowing skirt, tie-front bodice, and open back create a look that feels effortlessly romantic with just the right amount of allure.
Fit & Features
- Airy chiffon fabric, smooth knit lining
- V-neckline, spaghetti straps
- Crochet bodice detailing, cutout
- Open tie-back detail
- High front slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, elopements, courthouse weddings, destination weddings, bridal celebrations, engagement photoshoots, birthdays, vacations, honeymoons, formal soirees, cocktail parties
Style Number/Barcode: 05002-001690
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Good Things Coming Mini Dress
Featuring a draped cowl neckline, flirty front keyhole detail, and body-hugging fit, this mini dress was made for rooftop hotel bars, vacations, and night-out plans.
Fit & Features
- Knit fabric, high stretch
- Draped cowl neckline
- Adjustable straps
- Back strap detail
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000378
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: CHARTREUSE
Available Size: S, L
Product Badge:- Sale
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Somewhere Sunny Chiffon Mini Dress
This floral chiffon halter mini dress features a breezy swing silhouette and open back that feels effortless for tropical vacations, brunch, and every RSVP on your calendar.
Fit & Features
- Tropical floral print, chiffon-lined fabric
- Halter neckline, tie straps
- Open back design
- Flowy A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001212
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Edge Lace Ruffle Tie-Front Top
This lace tie-front top brings a flirty edge to your outfit lineup with delicate details, a curve-hugging fit, and endless styling potential from concert nights to weekend plans. Pair with the matching mini skort.
Shop Matching Bottoms: Flirty Edge Lace Ruffle Mini Skort
Fit & Features
- Sheer lace fabric with bust lining, high stretch
- Short cap sleeves
- Tie-front closure with ruffled trim
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06202-000103
Category Name: Vacation Looks
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seas The Day Tropical Sequin Mini Tube Dress
Vacation mood: activated. This tropical print sequin mini tube dress hugs in all the right places with a bodycon fit that’s ready for beachside dinners, rooftop cocktails, and every photo-worthy plan in between.
Fit & Features
- Tropical printed knit fabric with lining, moderate stretch
- All-over clear sequin embroidery
- Strapless straight-across neckline
- Side zipper and hook-eye closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000884
Category Name: Vacation Looks
Price: $10.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Salt Air Striped Knit Cutout Maxi Dress
Vacation photos are optional, but compliments won't be. This striped knit cutout maxi dress hugs your curves with statement O-ring details and a leg-baring slit that was made for turning heads.
Fit & Features
- Abstract striped textured knit fabric, moderate stretch
- Sleeveless sweetheart neckline
- O-ring halter design, tie-back halter spaghetti straps
- Waist cutout with O-ring design
- Open back, bar strap with hook-eye closure, lower back zipper closure
- Maxi-length hem, high-cut side slit, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000590
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Making Headlines Glitter Mini Dress
This glitter metallic mini dress brings the drama with a plunge cowl halter neckline, bodycon fit, and just enough shimmer to keep every eye locked in your direction.
Fit & Features
- Glitter metallic fabric, sewn-in knit lining
- Plunge cowl halter neck, tie straps
- Open back
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05103-000970
Category Name: Vacation Looks
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Maddie Halter Beaded A-Line Formal Dress
Special Occasion
The Maddie formal dress blends effortless glamour with modern allure. Crafted from a soft slinky knit, this floor-length silhouette features a beaded halter neckline, subtle ruching, and an elegant draped front detail that moves beautifully with every step.
Fit & Features
- Sinky knit stretchy fabric, smooth knit lining, high stretch
- Halter neckline, detachable stone beaded necklace with lobster clasp closure
- Padded bra cups, non-slip grip lining
- A-line flowy silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Destination weddings, cocktail parties, birthday dinners, vacations, resorts, anniversaries, date nights, and engagement parties.
Style Number/Barcode: 05002-001581
Category Name: Vacation Looks
Price: $29.97 $89.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Coast To Cocktails Striped Maxi Dress
The dress that belongs in your vacation photo dump. With a plunging halter neckline, textured striped knit, and an open tie-back design, this maxi dress was made for ocean views, dinner reservations, and weekend escapes.
Fit & Features
- Striped pattern, sheer texture crochet knit fabric
- Halter neckline, tie straps
- Open tie-back
- High side slit
- Curve-hugging, long hem
- Runs true to size
Style Number/Barcode: 05102-000591
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Sale
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Island Time Floral Ruffle Dress
Your out-of-office reply just found its dress. With a vibrant tropical print, flirty cutout detail, and layers of playful ruffles, this mini dress was made for vacations, sunset cocktails, and every photo op in between.
Fit & Features
- Tropical print, mesh fabric, soft knit lining
- Halter neckline, hardware insert, tie straps
- Keyhole cutout
- Form-hugging fit
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000706
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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One More Look Lace Ruffle Romper
The romper that changes the whole mood. This lace halter romper combines a plunging neckline, flattering ruching, and a flouncy layered hem that's playful and unforgettable.
Fit & Features
- Lace fabric, knit lining
- Plunge halter neckline, tie straps
- Open back
- Form-hugging bodice
- Layered ruffle mini-length hem
- Built-in shorts knit lining
- Runs true to size
Style Number/Barcode: 06503-000323
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: CHARTREUSE, BROWN
Available Size: XS, S, M, L
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Vacay Behavior Seashell Trim Mini Dress
Vacation behavior starts the second this dress goes on. With a seashell trim, daring cutouts, and a curve-loving bodycon fit, this mini dress was made for making every arrival feel a little more unforgettable.
Fit & Features
- Slinky knit fabric, knit lining, high stretch
- Sleeveless plunging V-neckline, bar strap detail, tie-back halter straps
- Seashell trim, O-ring cutout at the waist
- Waist cutouts leading to an open back, tie-back straps, adjustable strap
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000929
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Upgrade Floral Halter Ruffle Romper
Your weekend plans just found their outfit. This floral halter ruffle romper combines a draped cowl neckline, cascading ruffles, and an open back for a look that feels playful, flirty, and ready for every RSVP.
Fit & Features
- Abstract floral print mesh fabric with knit lining, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Tie-back halter straps, open back, lower tie-back spaghetti straps
- Drop waist design, side ruffled accent
- Tiered ruffled overlay with mini-length hem, A-line fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000288
Category Name: Vacation Looks
Price: $42.90
Availability: Out of Stock
Product Badge:- Ships Free
- Abstract floral print mesh fabric with knit lining, high stretch
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Chic On Arrival O-Ring Straw Clutch
The chic touch your outfit didn’t know it needed. This O-ring clutch brings texture, style, and just the right amount of attention, whether you're headed to brunch, a wedding, or a last-minute dinner reservation.
Fit & Features
- Rectangular shape
- Top metal O-ring handle
- Attachable chain-link shoulder strap
- Natural Color: Straw material
- Black Color: Faux leather material
Style Number/Barcode: 07203-000171
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: NATURAL
Available Size: NS
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Sleek And Flirty High-Slit Midi Skirt
This flowy midi skirt was made for nights when subtle just isn’t the mood. The ruched waist, high-cut side slit, and A-line fit keep it sleek, flirty, and impossible to ignore from every angle. Style with the matching halter top.
Shop Matching Top: Sleek And Flirty Cowl Neck Halter Top
Fit & Features
- Sleek knit fabric, high stretch
- High-rise waist, ruched detailing
- High-cut side slit
- Asymmetric midi-length hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 06501-000149
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: TEAL
Available Size: L
Product Badge:- Part of a Set
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Marsha Floral Tie-Back Formal Dress
Special Occasion
The Marsha formal dress brings effortless drama with every step. This floral mesh mermaid gown features a softly draped neckline, an open tie back, and a figure-skimming silhouette that feels equal parts polished and striking.
Fit & Features
- Statement floral print, mesh fabric, knit lining
- Cowl neckline
- Open tie-back detail
- Mermaid form-hugging silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Vacations, honeymoons, resort getaways, destination weddings, date nights, birthday dinners, anniversaries, and cocktail soirees.
Style Number/Barcode: 05002-001587
Category Name: Vacation Looks
Price: $29.97 $69.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Trendy Fab Floral Beaded Sequin Halter Top
Shop Matching Bottoms: Trendy Fab Floral Beaded Sequin Mini Skirt
Fit & Features
- Woven fabric
- Floral beaded and sequin embroidered design
- Sleeveless high halter neckline
- Open cross-back strappy design with tie closure
- Hidden side zipper closure
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06003-000378
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Yours Slinky Knit Poncho
One of those tops that somehow works with everything and still stands out. This slinky knit poncho drapes effortlessly with an off-the-shoulder neckline and asymmetric hem that pairs perfectly with denim, shorts, or a sleek mini.
Fit & Features
- Slinky knit fabric, high stretch
- Off-the-shoulder neckline
- Short sleeves
- Asymmetric hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06001-000746
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrist Candy Four-Pack Bangle Set
This statement four-pack bangle bracelet stack brings instant polish to everything from swimwear and sundresses to your favorite going-out look, making styling feel effortlessly pulled together.
Fit & Features
- Four-pack bangle bracelet set
- Two sleek metal bangles
- Two chunky square-shaped bangles
Style Number/Barcode: 07003-000260
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Backless Behavior Halter Mini Dress
This dress definitely started a few unnecessary crushes. The bodycon fit, cowl halter neckline, and attached triangle bikini top bring serious vacation confidence, while the side ruffle sashes and open back keep every angle working overtime.
Fit & Features
- Slinky knit fabric, knit lining
- Plunge halter cowl open neckline
- Attached string triangle bikini top
- Open back
- Bodycon mini-length silhouette
- Attached side ruffles
- Runs true to size
Style Number/Barcode: 05103-001029
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S
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Weekend Plans Satin Halter Crop Top
Serving date night, rooftop drinks, and every plan worth dressing up for. This satin halter top features a draped cowl neckline and an open tie-back design that creates an effortlessly elevated look from every angle.
Fit & Features
- Smooth satin fabrication
- Sleeveless plunge halter neckline
- Open back
- Adjustable neck and back tie closures
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000583
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L
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Disco Daisy Beaded Mini Skort
This skort came to collect compliments. Covered in floral beadwork and shimmering sequins with a scalloped hem, it’s the piece you throw on when the dress code is extra.
Fit & Features
- Floral bead and sequin-embellished pattern
- Sheer mesh fabric, built-in knit shorts
- Side zipper and hook-eye closure
- Form-hugging fit
- Scallop trim mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000155
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: L