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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Sultry Fave Halter Cowl Neck Floral Maxi Dress
You'll always embody sultriness in this floral mesh maxi dress perfect for weddings or cocktail parties! The halter cowl neckline with tie adds a touch of charm, while the form-hugging silhouette highlights your curves. The maxi-length hem and floral print mesh fabric bring an elegant and romantic touch. Complete the look with rhinestone earrings and a clutch.
Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Halter cowl neckline with tie
- Form-hugging silhouette
- Maxi-length
- Runs true to size
Style Number/Barcode: 05101-3331
Category Name: Vacation Dresses & Outfits
Price: $45.90
Availability: Out of Stock
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Awaken Beauty A-Line Lace Short Dress
Transform into a vision of beauty in this lace short dress at every party! This stunning dress boasts a sleeveless square neckline with a tie, enhancing your feminine charm. The A-line silhouette and short-length hem flatter your figure, while the intricate lace fabric adds a touch of elegance. Complete the look in stiletto mules and a purse!
Fit & Features
- Lace fabric lined with stretchy knit
- Square neckline with tie
- Wide shoulder straps
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5552
Category Name: Vacation Dresses & Outfits
Price: $38.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, M, L
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Such A Flirt Sweetheart Lace Trim Skater Dress
This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.
Fit & Features
- Sheer chiffon woven fabric with stretchy knit lining
- Lace trim sweetheart neckline with bow detail, bust underwire
- Adjustable lace trim shoulder straps
- Partially smocked back with zipper and hook-eye closure
- Lace trim bodice, drop waist seam
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3461
Category Name: Vacation Dresses & Outfits
Price: $49.90
Availability: In Stock
Available Color: PINK
Available Size: 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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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
Product Badge:- Sale
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Smooth Talker Lace Bow Pleated Ponte Mini Dress
Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.
Fit & Features
- Smooth pointe knit fabric, minimal stretch
- Lace bow trim square neckline
- Spaghetti straps
- Fitted silhouette
- Pleated flare mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3661
Category Name: Vacation Dresses & Outfits
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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: S, M, L
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Sip Of Sultry Strapless Ruffle Mini Dress
Be the center of attention in this sultry strapless mesh mini dress! It features a strapless neckline with non-slip grip lining, and a ruffled trim adds a flirty touch while the bodycon silhouette highlights your curves down to the mini-length hem. Complete the look in heels and teardrop earrings.
Fit & Features
- Strapless neckline
- Non-slip grip lining
- Side zipper and hook-eye closure
- Ruffle trim, bodycon silhouette
- Mini-length hem
- Mesh fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-3660
Category Name: Vacation Dresses & Outfits
Price: $42.90
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: 07109-0407
Category Name: Vacation Dresses & Outfits
Price: $4.97 $14.90
On Sale: Yes
Availability: In Stock
Available Color: MAUVE, NUDE, BLACK
Available Size: S, M, L
Product Badge:- Sale
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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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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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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: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- 20% Off
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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: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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: $9.97 $21.90
On Sale: Yes
Availability: In Stock
Available Color: MAUVE, WHITE
Available Size: S, M, L
Product Badge:- Sale
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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: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY, BLACK
Available Size: M, L, XS, S
Product Badge:- Sale
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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: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lavish Leopard Print Palazzo Wide-Leg Pants
Look lavish in these leopard palazzo pants boasting a mid-rise waist and wide-leg silhouette perfect for elevating your look. Style with a crop top and heels.
Fit & Features
- Smooth woven fabric, no stretch
- Leopard print
- Elasticized mid-rise waist
- Wide-leg pant
- Pants in size small have an 11.5" front rise with a 28" inseam
- 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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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: $26.97 $59.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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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
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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: Out of Stock
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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: $19.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: HEATHERGRAY
Available Size: S, M, L
Product Badge:- Sale
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Reusable Gel Lift Pasties
These gel bra pasties create the perfect lift and nipple coverage for a smooth look. The supportive sticky bra design with its adhesive interior gently lifts the breasts and perfectly covers the nipples for a seamless look. Wear these bra pasties underneath an open-back halter top or strapless cocktail dress with a smooth shapewear style for the ultimate flawless ensemble. Wear with a sleeveless top and a cute pair of denim for your next-day date.
Fit & Features
- One pair
- Gel pasties
- Reusable, can be worn up to 25 times
- Provide smoothing, lifting, and supporting effects
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07101-0272
Category Name: Vacation Dresses & Outfits
Price: $9.90
Availability: In Stock
Available Color: NATURAL
Available Size: NS
Product Badge:- Best Seller