Vacation Dresses & Outfits
Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.
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Winter Vacation Dresses & Outfits Ready For Fun!
Windsor’s collection of vacation dresses and vacation clothes has everything you need for your next winter getaway. Choose from stylish dresses that can be layered with cozy jackets or soft sweaters for cooler nights. Our vacation clothes include flowy skirts, comfy pants, trendy shorts, and cute tops perfect for any destination. Whether you’re packing for a beach vacation or a cozy mountain retreat, find the perfect look in-store or online. Shop Windsor to make winter vacation style easy and fun!
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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 Dresses & Outfits
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
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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 Dresses & Outfits
Price: $64.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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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 Dresses & Outfits
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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 Dresses & Outfits
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
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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 Dresses & Outfits
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
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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 Dresses & Outfits
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
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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 Dresses & Outfits
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
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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 Dresses & Outfits
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
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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 Dresses & Outfits
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 Dresses & Outfits
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
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Cozy Staple Faux Fur Ankle Booties
Fit & Features
- Flat sole
- Ankle-fit
- Almond toe
- Faux suede exterior
- Faux fur lined insole
- Runs true to size
Style Number/Barcode: 07403-1804
Category Name: Vacation Dresses & Outfits
Price: $28.90
Availability: In Stock
Available Color: TAN-2
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- Best Seller
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Glow Up Button-Front Cropped Vest
Fit & Features
- Lurex knit fabric
- Sleeveless V-neckline
- Single button-front closure
- Fitted cropped ribbed hem
- Runs true to size
Style Number/Barcode: 06005-2149
Category Name: Vacation Dresses & Outfits
Price: $26.90
Availability: In Stock
Available Color: GOLD
Available Size: XS, S, M, L
- Lurex knit fabric
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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 Dresses & Outfits
Price: $18.90
Availability: Out of Stock
Product Badge:- Best Seller
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Party Hour Rhinestone Beer And Lime Earrings
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 Dresses & Outfits
Price: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Cozy Luxe Lurex Knit Pants
Fit & Features
- Lurex knit fabrication
- Mid-rise waist
- Drawstring waist
- Straight-leg fit
- Runs true to size
Style Number/Barcode: 06502-2556
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: GOLD
Available Size: XS, S, M, L
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Pretty Aura Floral Print Strapless Crop Top
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 Dresses & Outfits
Price: $26.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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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 Dresses & Outfits
Price: $7.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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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: 05101-3377
Category Name: Vacation Dresses & Outfits
Price: $64.90
Availability: In Stock
Available Color: WHITE, BLACK, WINE
Available Size: XS, S, M, L, XL
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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 Dresses & Outfits
Price: $22.90
Availability: In Stock
Available Color: IVORY, COGNAC
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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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 Dresses & Outfits
Price: $49.90
Availability: In Stock
Available Color: LEOPARD
Available Size: S, M, L
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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 Dresses & Outfits
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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50s Icon Halter Plunge Neck Skater Romper
Chanel a popular 50s iconic look in this halter plunge skater romper perfect for themed parties or summer holidays! With a flattering halter neckline and charming tie closure, this romper will create a stunning silhouette. The skater shape and short hem add to its playful appeal. Complete the look with hoop earrings.
Fit & Features
- Smooth cotton-blend knit fabric, moderate stretch
- Halter plunge neckline, tie closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06503-1138
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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 Dresses & Outfits
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Grandeur Blooms Strapless Slit Floral Maxi Dress
Gorgeous blooms dance across this floral maxi dress making every entrance statement worthy! Perfect for cocktail parties or dressy dinners, this strapless dress boasts a form-hugging fit, a high side slit allowing for movement, and a maxi-length hem. Complete the look with a clutch purse and heels.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Strapless neckline
- High side slit
- Form-hugging fit
- Runs true to size
- Please note flower placement may vary
Style Number/Barcode: 05101-3386
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: BLACK, BROWN
Available Size: XS, S, M, L