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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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: 05101-3763
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: BLACK-2
Available Size: XS, S, M, L
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Read All About It Newspaper Bodycon Mini Dress
Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.
Fit & Features
- Newspaper print, knit fabric with stretchy lining
- Adjustable spaghetti straps
- Sweetheart neckline with lace trim
- Back zipper and hook-eye closure
- Built-in padded underwire bust
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5578
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
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One Sided Sleeveless Cutout Bodysuit
Show off your good side in this sleeveless bodysuit for any casual plans! Featuring a cutout one-shoulder neckline, this form-hugging bodysuit is designed to accentuate your curves. The thong bottom with snap button closures adds a secure fit. Complete the look in denim shorts for a day out.
Fit & Features
- Double-lined brushed knit stretchy fabric
- Cutout one-shoulder neckline
- Form-hugging fit
- Thong bottom, snap-button closures
- Runs true to size
Style Number/Barcode: 06001-5237
Category Name: Vacation Dresses & Outfits
Price: $24.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Unique Addition Strapless Cut Out Tube Crop Top
A chic strapless tube top makes a unique addition to your fashion lineup! The cutest date or night-out top features a strapless neckline, a trendy side cutout with an adjustable drawstring, and an asymmetrical cut cropped hem. Complete the look in a cute mini skirt and your favorite heels.
Fit & Features
- Soft knit stretchy fabric
- Strapless neckline
- Side cutout, adjustable drawstring
- Asymmetrical cut cropped length
- Runs true to size
Style Number/Barcode: 06001-5377
Category Name: Vacation Dresses & Outfits
Price: $9.97 $21.90
On Sale: Yes
Availability: In Stock
Available Color: SAGE, MAUVE
Available Size: L, XL, XS, S, M
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Trendy Girl High-Rise Slit Denim Skort
The perfect denim skort for a trendy girl like you to dress up! This high-rise waist skort features a flattering bodycon fit and dual front slits for added style. The skirt overlay with shorts lining provides comfort and coverage while the mini-length adds a touch of playful charm. Complete the look in a corset top to make a statement!
Fit & Features
- Denim fabric, minimal stretch
- High-rise waist, back zipper closure
- Bodycon fit
- Dual front slits
- Skirt overlay, shorts lining
- Runs true to size
Style Number/Barcode: 06603-0398
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: TAN, IVORY, DARK, DENIM
Available Size: S, M, L, XL, XS
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Denim Diva Square Toe Block Heels
Fall head over heels for these denim block heels! Strut like a diva in these shoes featuring a square toe, a wide band, a block heel, and a luxe fit cushioned faux leather insole for comfort. Complete the look with a trendy handbag for any occasion!
Fit & Features
- 3" Block Heel
- Square toe
- Wide band
- Luxe fit cushioned faux leather insole
- Denim material
- Runs true to size
Style Number/Barcode: 07401-4885
Category Name: Vacation Dresses & Outfits
Price: $26.90
Availability: In Stock
Available Color: DENIM
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Everyday Beauty Sleeveless A-Line Mini Dress
This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.
Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5631
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Adorable Basic Scoop Neck Seamless Crop Top
You'll always feel adorable in this basic crop top perfect for layering or styling on its own! The top is crafted from a seamless knit fabric offering plenty of stretch and comfort. It features a flattering scoop neckline, shoulder straps, and a fitted crop hem. Complete the look in denim shorts.
Fit & Features
- Seamless knit fabric, moderate stretch
- Scoop neckline
- Shoulder straps
- Fitted crop length
- Runs true to size
Style Number/Barcode: 07109-0408
Category Name: Vacation Dresses & Outfits
Price: $14.90
Availability: In Stock
Available Color: BROWN, MAUVE, NUDE, BLACK
Available Size: S, M, L
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Casual Chic Style Long Sleeve Ribbed Knit Midi Dress
The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.
Fit & Features
- Hacci ribbed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5920
Category Name: Vacation Dresses & Outfits
Price: $38.90
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L
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Love Of Details V-Neck Lace-Up Skater Dress
Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.
Fit & Features
- Lace fabric line with stretchy knit
- Adjustable spaghetti straps, V-neckline
- Back zipper and hook-eye closure
- Mesh lace-up bodice
- Asymmetrical ruffles
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3436
Category Name: Vacation Dresses & Outfits
Price: $59.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress
Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.
Fit & Features
- Floral tie-dye print, smooth knit fabric, moderate stretch
- Strapless neckline
- Lace-up back design
- Form-hugging fit
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3277
Category Name: Vacation Dresses & Outfits
Price: $49.90
Availability: In Stock
Available Color: MAUVE
Available Size: XS, S, M, L
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Sweetly Coy V-Neck Slit Lace Crop Top
Enhance your everyday style in this lace crop top featuring a V-neckline with a twist accent, spaghetti straps, and a center slit design. The lace-lined fabric offers stretch and a romantic look.
Fit & Features
- Lace lined fabric, minimal stretch
- V-neckline with twist
- Spaghetti straps
- Center slit
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06001-5431
Category Name: Vacation Dresses & Outfits
Price: $21.90
Availability: In Stock
Available Color: MAUVE, WHITE
Available Size: XS, S, M, L
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Beachy Vibes Bell Sleeve Tie-Front Top
This airy lightweight knit tie-front top gives off those effortless beachy vibes! It features a scoop neckline, a dual tie-front design, long flared bell sleeves, a cute scalloped front hem, and a mid-length, relaxed fit. The sheer knit fabric features a textured ribbed pattern. Layer over a basic bodysuit and style with light-wash denim.
Fit & Features
- Scoop neckline
- Dual tie-front design, thin straps
- Long bell sleeves
- Scalloped front hem
- Mid-length, relaxed fit
- Sheer knit fabric, textured ribbed pattern, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0400
Category Name: Vacation Dresses & Outfits
Price: $29.90
Availability: In Stock
Available Color: IVORY, BLACK
Available Size: XS, S, M, L
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Lavish Leopard Print Palazzo Wide Leg Pants
Fit & Features
- Smooth woven knit fabrication
- Elasticized mid-rise waist
- Leopard print
- Wide leg pant
- Runs true to size
Style Number/Barcode: 06402-1449
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: LEOPARD
Available Size: XS, S, M, L
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Sangria Sunset Strapless Paisley Satin Crop Top
The perfect paisley satin crop top to wear during sunset cocktail hour! Crafted from a silky satin fabric with a summery paisley print, this crop top elevates every outfit. It features a strapless neckline and stretchy smocked back, a flirty tie design, and a pointed cropped hem that flaunts your figure. Complete the look in denim jeans and strappy sandals.
Fit & Features
- Paisley print, satin fabric, no stretch
- Strapless neckline
- Tie back design, smocked back
- Pointed cropped length
- Runs true to size
Style Number/Barcode: 06003-2614
Category Name: Vacation Dresses & Outfits
Price: $26.90
Availability: In Stock
Available Color: BURGUNDY, BROWN
Available Size: XS, S, M, L
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Done In One Zip-Front Tie-Waist Denim Romper
Designed to be your new favorite done in one piece, this denim romper offers a cute and flattering style year-round! It's designed with classic short sleeves and collar neckline, a zip-front closure, two flap pockets and side pockets for convenience, a tie-waist belt that cinches your waistline, and a form-hugging fit. Complete the look with sleek hoop earrings and your fave sneakers!
Fit & Features
- Denim fabric, slight stretch
- Short sleeves and collar neckline
- Zip-front closure
- Two flap pockets, side pockets
- Tie-waist belt
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0400
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Adorable Chic Bow Cutout Bodycon Mini Dress
Adorable chic and ready to be seen, this sleeveless mini dress is everything! It features adjustable spaghetti straps for a customizable fit, a sweetheart neckline adorned with a statement bow, and a cutout bust to show a peak of skin along the bodycon silhouette. Complete the look in high heels.
Fit & Features
- Smooth knit fabric lined with knit
- Adjustable spaghetti straps
- Sweetheart neckline with bow
- Cutout bust
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5697
Category Name: Vacation Dresses & Outfits
Price: $29.90
Availability: In Stock
Available Color: FUCHSIA, BLACK
Available Size: S, M, L
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Stylish Occasion Satin Cargo Mini Skirt
The perfect stylish satin mini skirt for any occasion! Crafted on silky stretch satin, this skirt features a flattering high-rise waist, a form-hugging fit, dual side flap pockets, and a mini-length hem. Complete the look with a sleek moto jacket and boots!
Fit & Features
- High-rise waist
- Front hidden zipper and hook closure
- Form-hugging fit
- Dual side flap pockets. mini-length hem
- Silky stretch satin-lined fabric
- Stretchy knit shorts lining
- Runs true to size
Style Number/Barcode: 06403-0438
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: PINK, BLACK
Available Size: S, M, L, XS
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Icing On The Cake V-Neck Lace Skater Dress
The perfect lace skater dress that'll take your day somewhere magical! Perfect for rehearsal dinners, birthdays, or graduation. This dress features a flattering V-neckline, spaghetti straps, and a playful cross-back design. Its skater silhouette and surplice ruffled short-length hem will keep you twirling all day! Complete the look in strappy block heels.
Fit & Features
- Lace fabric lined with stretchy knit
- V-neckline, spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3667
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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Enticing Sass Halter Cutout Wide-Leg Jumpsuit
Unlock the sass in this sleeveless knit jumpsuit featuring a sultry halter neckline, a cutout front, and a flattering wide-leg silhouette perfect for styling with sandals. The smooth knit fabric offers a comfortable stretch.
Fit & Features
- Smooth knit fabric, moderate stretch
- Halter neckline, spaghetti strap tie
- Cutout front
- Wide-leg silhouette
- Jumpsuit has a 12.5” front rise with a 33” inseam
- Runs true to size
Style Number/Barcode: 06502-2535
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: PLUM, TAUPE
Available Size: XS, S, M, L
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Strut And Snap Ribbed Knit Midi Dress
Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Ribbed knit fabric with moderate stretch
- Square neckline
- Tank shoulder straps
- Metal button accents
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1167
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: XS, S, M, L
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Weekend Feeling Sleeveless Bubble Hem Mini Dress
A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.
Fit & Features
- Knit fabric, moderate stretch
- Crew neckline
- Form-hugging fit
- Drop waist seam, bubble mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5873
Category Name: Vacation Dresses & Outfits
Price: $29.90
Availability: In Stock
Available Color: HEATHERGRAY
Available Size: XS, S, M, L
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Confident Moves Crew Neck Ruffled Mini Dress
Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.
Fit & Features
- Smooth double-lined knit fabric, moderate stretch
- Crew neck
- Bodycon fit
- Tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5792
Category Name: Vacation Dresses & Outfits
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: M, L
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Trendy Shades Square Sunglasses
Discover these trendy sunglasses perfect for any sunny day to keep your style on point! They feature a small square shape, tinted UV protective lenses, and comfortable arms and nose support. Complete the look with platform sneakers for a casual day out.
Fit & Features
- Small square shape
- Tinted UV protective lenses
- Comfortable arms and nose support
Style Number/Barcode: 07008-1089
Category Name: Vacation Dresses & Outfits
Price: $9.90
Availability: In Stock
Available Color: BLACK
Available Size: NS