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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Scene Set Statement Earrings
Polished with a little bite. These statement earrings bring glossy teardrop stones and textured metal trim for a sleek finish that elevates a simple outfit.
Fit & Features
- Statement drop earrings
- Glossy teardrop stone design
- Textured metal trim
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000439
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Late Checkout Cat Eye Sunglasses
Vacation mode mentally, even if you’re just grabbing coffee. These cat eye sunglasses bring a sleek throwback vibe that instantly makes denim, basics, and messy buns feel styled.
Fit & Features
- Lightweight plastic frame
- Cat eye silhouette
- Tinted lenses
- Slim arms with polished hardware accents
Style Number/Barcode: 07008-000238
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Petal Drama Floral Earrings
Big florals, bigger plans. These oversized sculptural flower earrings bring a polished finish with textured metal petals that instantly dress up everything from vacation looks to wedding guest dresses.
Fit & Features
- Oversized sculptural flower design
- Textured petals with contrast trim
- Statement silhouette
- Polished metal finish
- Post back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000441
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Escape The City Metallic Wedges
These metallic wedge sandals bring vacay energy with a glossy metallic finish and adjustable ankle strap—made for sunset dinners, beachside strolls, and weekend trips.
Fit & Features
- 4.5" wedge heel
- Almond toe
- Clear PVC toe strap
- Adjustable ankle strap with buckle closure
- Cushioned footbed
- Espadrille and metallic material
- Runs true to size
Style Number/Barcode: 07406-000052
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: GOLD
Available Size: 8, 8.5, 9, 10
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Stacked And Booked Bangle Bracelet Set
Your outfit called and said it needed these. This bangle bracelet set mixes resin textures, sleek metal details, and mini rhinestone accents for the kind of stack that makes even a basic tee feel planned.
Fit & Features
- Five-pack bangle bracelet set
- Two resin bangles
- Three metal bangles
- Assorted silhouettes and designs
- Mini rhinestone embellishments
Style Number/Barcode: 07003-000307
Category Name: Vacation Looks
Price: $15.90
Availability: In Stock
Available Color: GREEN
Available Size: NS
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Wild Card Sheer Mesh Poncho Top
Throw it on and suddenly your outfit has something to say. This abstract animal print sheer mesh poncho top layers effortlessly for nights out, last-minute plans, or whenever your look needs a little edge.
Fit & Features
- Abstract animal print
- Sheer mesh fabric
- Relaxed poncho silhouette
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000704
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: BROWN
Available Size: L
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Picnic Flirt Eyelet Mini Dress
Sweet, but with a little attitude—just how we like it. This eyelet skater dress shapes you with a corset bodice and flexible boning, while the flutter sleeves and lace-up back keep it playful for every dressy event.
Fit & Features
- Eyelet woven fabric, woven lining
- Sweetheart neck, ruffle trim, bust tie
- Flutter short sleeves
- Lace-up back, zipper and hook-eye closure
- Corset bodice, flexible boning
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001431
Category Name: Vacation Looks
Price: $25.97 $56.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Sweet Tea Flirt Mini Dress
This is the kind of dress that accidentally becomes your whole personality for the summer. Between the tiny floral print, smocked waist, and floaty skater fit, it’s basically made for farmers market mornings, brunch, and daytime celebrations.
Fit & Features
- Delicate floral print, woven fabric
- Square neckline
- Wide shoulder straps
- Stretchy socked bodice
- Ruffled skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001479
Category Name: Vacation Looks
Price: $28.97 $62.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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Day Date Floral Print Puff Sleeve Midi Dress
Effortless plans, elevated instantly. This floral print midi dress brings that easy, cinched-in fit with a pretty, flowy feel—perfect for brunch dates, garden parties, and everything in between.
Fit & Features
- Cotton-blend fabric with lining
- Floral print
- Square neckline, ruched bust
- Short puff sleeves with cinched hems
- V-shaped waist seam, stretchy smocked back
- Midi-length flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-001394
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: WHITE, PRINT
Available Size: S
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Flirtatious Floral Mesh Ruffle Slit Midi Dress
Florals with a little flirt built in. This stretch mesh midi dress pairs a draped cowl neckline with a ruffle slit that moves effortlessly through parties, dinner dates, and dressed-up plans.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless sweetheart neckline, draped cowl neck overlay, padded bust
- Adjustable spaghetti straps
- High-cut front slit, ruffled hem
- Midi-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-001359
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Wild Style Animal Print Hot Shorts
Wild mix, trendy vibes. These animal print hot shorts bring a mid-rise waist and form-hugging fit for a statement piece that does the styling for you. Pair with the matching poncho.
Shop Matching Top: Wild Style Animal Print Poncho
Fit & Features
- Knit fabric, high stretch
- Multi-animal print pattern
- Mid-rise fold-over waist
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06503-000389
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: LEOPARD
Available Size: S, M, L
Product Badge:- Part of a Set
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Lush Floral Print Strapless Maxi Dress
Summer plans just found their dress. The floral print maxi dress pairs a softly draped strapless neckline with a high side slit for an effortless statement. Wear it to destination celebrations, cocktail parties, and on vacation dinners.
Fit & Features
- Floral print, mesh fabric, brushed knit lining
- Strapless draped neckline
- High side slit
- Sleek curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001634
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
- Floral print, mesh fabric, brushed knit lining
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Windsor x Ed Hardy Tiger Sunglasses
A sharper way to throw shade. These Ed Hardy rectangular sunglasses pair bold angular frames with tiger head graphics for concert weekends, street style, and outfits with bite.
Fit & Features
- Tinted rectangular lenses
- Bold angular full-rim frame
- Ed Hardy logo on the lens
- Tiger head graphic side accents
- Wide arms with Ed Hardy logo detail
Style Number/Barcode: 07008-000292
Category Name: Vacation Looks
Price: $25.00
Availability: In Stock
Available Color: BLACK
Available Size: NS
Product Badge:- New Arrival
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Sandy Shores Tropical Floral Maxi Skirt
This vibrant tropical floral maxi skirt will transport you to the sandy shores of a tropical paradise. With its stunning print and high-rise waist, this maxi skirt is perfect for any summer occasion. Pair with the matching top.
Fit & Features
- Tropical floral print, stretchy knit fabric
- High-rise waist
- Curve-hugging maxi silhouette
- Runs true to size
Shop the Matching Top: Sandy Shores Tropical Floral Crop Top
Style Number/Barcode: 06501-000171
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Stop And Stare Halter Top
Pretty, but definitely not predictable. This halter top combines a striking floral print with a plunging neckline and curve-hugging fit for the kind of outfit that instantly moves to the top of your weekend lineup.
Fit & Features
- Mesh fabric, sewn-in knit lining
- Plunge halter neck, tie straps
- Side ruched seams
- Floral graphic print
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000670
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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No Small Talk Oval Sunglasses
The outfit needed one final opinion. These oval sunglasses bring a sleek narrow shape and dark lenses for errands, brunch plans, and every casually overdressed entrance.
Fit & Features
- Slim oval silhouette
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000192
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
Product Badge:- New Arrival
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Soft Romance Floral Lace Poncho Top
The sheer poncho shape gives fitted bottoms a softer counterpoint. This cropped lace top pairs an asymmetrical neckline with long sleeve accents for an easy layered effect. Style it with a bandeau top and denim shorts when the outfit needs more texture.
Fit & Features
- Sheer floral lace fabrication
- Asymmetrical neckline
- Cropped poncho silhouette
- Long sleeve accents
- Runs true to size
Style Number/Barcode: 06001-000800
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Soft Cascade Ruffle A-Line Maxi Dress
Let the ruffles do the outfit planning. This A-line maxi dress pairs a plunging neckline and smocked empire waist with a cascading front detail for soft movement. Add bold jewelry and sleek sandals for an easy warm-weather look.
Fit & Features
- Gauze woven fabrication
- Plunging V-neckline with spaghetti straps
- Smocked empire waist
- Open back with tasseled tie detail
- Cascading front ruffle
- Flowy A-line maxi-length fit
- Runs true to size
Style Number/Barcode: 05102-000672
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival