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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Raise The Bar Wide-Leg Jumpsuit
Fit & Features
- Smooth knit fabric, plenty of stretch
- Plunging sleeveless halter neckline
- Halter neck ties
- Open back
- Wide-leg silhouette
- Jumpsuit in size small is 58" shoulder to hem with a 13" front rise and a 30" inseam
- Runs true to size
Style Number/Barcode: 06502-2551
Category Name: Vacation Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: RUST, BLACK
Available Size: S, M, L
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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
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Just Your Stripe Off-The-Shoulder Crop Top
This striped crop top is just what you're looking for! It's designed on stretchy rib knit fabric with a trendy striped print, an off-the-shoulder neckline to bare some skin, and a flirty cropped hem. Complete the look in denim shorts for casual plans.
Fit & Features
- Striped rib knit stretchy fabric
- Off-the-shoulder neckline
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1972
Category Name: Vacation Dresses & Outfits
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Stole Your Heart Charms Shield Sunglasses
These shield sunglasses will steal your heart! They showcase side heart charms for a trendy vibe, oversized tinted lenses, rubber nose supports, and comfortable arms. Complete the look in a cute jumpsuit.
Fit & Features
- Shield style oversized tinted lenses
- Side heart charms
- Rubber nose supports
- Comfortable arms
Style Number/Barcode: 07008-1093
Category Name: Vacation Dresses & Outfits
Price: $11.90
Availability: In Stock
Available Color: PINK
Available Size: NS
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Pair To Perfection Metallic Lace-Up Sneakers
These metallic sneakers pair perfectly with your everyday outfits. They feature a round-toe, a lace-up front closure, and a rubber gum sole.
Fit & Features
- Round toe
- Metallic material
- Lace-up front closure
- Rubber gum sole
- Runs true to size
Style Number/Barcode: 07407-0231
Category Name: Vacation Dresses & Outfits
Price: $28.90
Availability: In Stock
Available Color: SILVER
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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One Take V-Neck Ruffle Skater Romper
One take in this skater romper and you'll be so obsessed! Its adjustable spaghetti straps and bust tie enhance the ruffled V-neckline, while the tie-back design provides a flattering silhouette. The ruffled layered short-length hem adds a cute touch. Complete the look with a dainty necklace.
Fit & Features
- Knit fabric, moderate stretch
- Adjustable spaghetti straps
- Ruffle V-neckline
- Tie-back design
- Skater silhouette
- Ruffle layered short-length hem
- Runs true to size
Style Number/Barcode: 06503-1143
Category Name: Vacation Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: BLUSH, BLACK
Available Size: S, M, L, XS
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Sultry Example Tie-Front Lace Trim Crop Top
You'll be giving off plenty of sweet and sexy vibes in this crop top! Featuring delicate cap sleeves, a flattering lace trim scoop neckline, and dual tie-front closures, this crop top effortlessly adds a touch of romance to any outfit. Complete the look in denim jeans for any casual plans!
Fit & Features
- Rib knit fabric, moderate stretch
- Cap sleeves
- Lace trim scoop neckline
- Dual tie-front closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-0476
Category Name: Vacation Dresses & Outfits
Price: $24.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Breezy Boho Sheer Lace Asymmetric Maxi Skirt
Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties.
Fit & Features
- Sheer lace fabric with mini-length knit lining, plenty of stretch
- High-rise waist
- Ruching, adjustable drawstring
- High side slit
- Asymmetric maxi-length hem
- Flowy fit
- Runs true to size
Style Number/Barcode: 06501-1065
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Dancing Moves High-Rise Side Ruffle Midi Skirt
Dance all night in this midi skirt featuring a flattering high-rise waist, form-hugging silhouette, and a high side slit with a flirty ruffled trim perfect for styling with heels. The smooth knit fabric hugs your curves and offers plenty of stretch.
Fit & Features
- Smooth knit-lined stretchy fabric
- High-rise waist
- High-side slit with ruffle trim
- Form-hugging
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-1063
Category Name: Vacation Dresses & Outfits
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Confident Cutie Sleeveless V-Neck A-Line Mini Dress
Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!
Fit & Features
- Soft and stretchy rib knit fabric, full knit lining
- V-neckline
- Spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5651
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Feeling Daring Texture Knit Mini Skirt
Feel daringly stylish with this mini skirt! This ultra-trendy skirt features a high-rise waist, a bodycon silhouette, and a flirty mini-length hem on texture knit fabric. Dare to stand out and shop the matching top to complete the look!
Shop Matching Top: Feeling Daring Texture Knit Crop Top
Fit & Features
- High-rise waist
- Bodycon silhouette
- Mini-length hem
- Texture knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 06501-0999
Category Name: Vacation Dresses & Outfits
Price: $19.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
- High-rise waist
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Set For Good Cap Sleeve Slit Texture Crop Top
You'll be set for good in this stylish texture crop top all season! Featuring adorable cap sleeves, a V-neckline, and an adjustable bust drawstring atop a flirty slit along the cropped hem. Complete the look with the matching bottoms.
Shop Matching Bottoms: Set For Good High Rise Texture Mini Skirt
Fit & Features
- Texture sheer fabric, bust lining, minimal stretch
- Cap sleeves
- V-neckline
- Adjustable bust drawstring, center slit
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5287
Category Name: Vacation Dresses & Outfits
Price: $18.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Style Quotient Platform Denim Block Heels
Amp your style quotient in these sassy denim block heels perfect for any plans! The round toe and platform sole provide an elevated look, while the adjustable ankle strap with buckle closure secures the style. Complete the look in a mini dress and jacket.
Fit & Features
- 5" Block heel
- Round toe
- Platform sole
- Contrast straps
- Adjustable ankle strap, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4724
Category Name: Vacation Dresses & Outfits
Price: $32.90
Availability: In Stock
Available Color: DENIM
Available Size: 6, 7.5, 8, 8.5, 9, 10
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Sporty Luxe Corduroy Baseball Cap
Fit & Features
- Corduroy material
- Wide brim
- Baseball cap design
- Adjustable back strap
Style Number/Barcode: 07302-1736
Category Name: Vacation Dresses & Outfits
Price: $14.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: NS
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Breezy Style Sheer Crochet Cropped Sweater
This breezy sheer crochet cropped sweater is the perfect lightweight layer for the summertime! Designed with an airy open crochet knit fabric, it features a wide crew neckline, long loose sleeves for that boho vibe, a cropped hem, and a relaxed fit for an effortless look. Style with a charm necklace and hoop earrings.
Fit & Features
- Open crochet knit fabric, no stretch
- Crew neckline
- Long loose sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-1934
Category Name: Vacation Dresses & Outfits
Price: $22.90
Availability: In Stock
Available Color: NATURAL
Available Size: M, L, XL
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Flirty Does It Square Neck Rib Knit Bodysuit
You do flirty well in this rib knit bodysuit perfect for styling with your favorite high-waisted bottoms! Featuring a sleeveless square neckline with a V-wire notch and wide shoulder straps, it hugs your figure with a form-hugging fit. The thong bottom has convenient snap-button closures. Complete the look in best-selling bottoms and heels.
Fit & Features
- Rib knit stretchy fabric
- Square neckline with V-wire notch
- Wide shoulder straps
- Form-hugging fit
- Thong bottom, snap-button closures
- Runs true to size
Style Number/Barcode: 06002-1815
Category Name: Vacation Dresses & Outfits
Price: $24.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Charming Sweetness V-Neck Lace Trim Floral Crop Top
Unlock a charming sweetness in this floral crop top to dress up your everyday look! With delicate spaghetti straps and a lace trim V-neckline, it exudes a romantic appeal with a tiered ruffled silhouette and cropped hem. Complete the look in shorts and strappy sandals.
Fit & Features
- Floral print, mesh fabric, bust knit lining
- Spagehtti straps
- Lace trim V-neckline
- Tiered ruffled silhouette
- Runs true to size
Style Number/Barcode: 06001-5389
Category Name: Vacation Dresses & Outfits
Price: $24.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Everyday Cowgirl Colored Stone Straw Western Hat
Top off your cowgirl core look with this straw western hat at bachelorettes, festivals, or country bar nights! Made from distressed straw material for a rustic feel. Featuring a string tie bow adorned with a colorful stone and metal ball trim, this hat adds a touch of glam to the classic curved wide brim. Complete the look in cowboy boots.
Fit & Features
- String tie bow, colored stone and metal ball trim
- Classic curved wide brim
- Distressed straw material
Style Number/Barcode: 07302-1604
Category Name: Vacation Dresses & Outfits
Price: $12.97 $25.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- Sale
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Fresh Summer Vibes Wrap-Front Romper
Show off a fresh summer vibe in this elevated and chic woven romper. It features a sleeveless V-neckline, tank shoulder straps that lead to an open back with a cross-back lace-up design, a lower back cutout, a flattering high waist seam, a ruched wrap-front design with a short skirt overlay, and fitted shorts. Style with espadrille wedges for a cute daytime party look.
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Open back, cross-back lace-up design, tie closure
- Lower back cutout, zipper and hook-eye closure
- High waist seam, ruched wrap-front, short skirt overlay, fitted shorts
- Lined smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0407
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: M, XS, S, L
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Instant Fave Faux Suede Platform Sneakers
A pair of faux suede sneakers feature a round toe, rubber gum platform sole that elevates the look, a lace-up front, and a side striped design. Perfect for everyday styling.
Fit & Features
- Faux suede material
- Round toe
- Rubber gum platform sole
- Lace-up front
- Side striped design
- Runs true to size
Style Number/Barcode: 07407-0232
Category Name: Vacation Dresses & Outfits
Price: $30.90
Availability: In Stock
Available Color: BLACK/WHITE, BEIGE
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10, 5
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Blooming Chic Flower Detail Faux Leather Block Heels
Create a blooming chic 'fit perfect for the season with these cute block heels! Made with smooth faux leather, they feature an open square-shaped toe, a detailed toe strap with faux leather flower accents and faux pearl center beading, thin adjustable ankle and heel straps, and a sleek thin block heel. Style with the matching crossbody bag for an adorable look!
Shop Matching Bag: Blooming Chic Flower Detail Clear Crossbody Bag
Fit & Features
- 3" Thin block heel
- Faux leather upper
- Open square toe
- Toe strap, faux leather flower accents, faux pearl beading
- Adjustable ankle and heel straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4702
Category Name: Vacation Dresses & Outfits
Price: $30.90
Availability: In Stock
Available Color: WHITE
Available Size: 6, 6.5, 8, 8.5, 9, 10
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Sassy Style Ruched Knit Halter Skater Dress
Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!
Fit & Features
- Stretchy smooth knit, top knit lining
- V-neckline, tie-back halter straps
- Partially open back
- Ruched seams at the waist
- Double-layered skater skirt
- Fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05102-5832
Category Name: Vacation Dresses & Outfits
Price: $32.90
Availability: Out of Stock
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Cutest Vision Chain Link Trim Sunglasses
Any on-trend, sunny day look isn't complete without these sunglasses! They feature angular square-tinted lenses, rubber nose supports, and chain-link accent arms. Complete the look in sandals.
Fit & Features
- Angular square-tinted lenses
- Rubber nose supports
- Chain-link accent arms
Style Number/Barcode: 07008-1094
Category Name: Vacation Dresses & Outfits
Price: $10.90
Availability: In Stock
Available Color: ROSE, GOLD
Available Size: NS
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Born To Be Coveted Mid-Rise Lace-Up Denim Skort
A coveted summer style starts with this mid-rise denim skort perfect for casual plans! Made from denim fabric, this skort is perfect for showing off your legs in a flirty mini-length hem. Its mid-rise waist and form-hugging fit will accentuate your curves, while the playful skirt overlay with lace-up detailing and a slit adds a touch of edginess. Complete the look in a flirty crop top and sneakers.
Fit & Features
- Denim medium wash fabric, no stretch
- Mid-rise waist
- Back zipper hook-eye closure
- Lace-up, slit accent
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0379
Category Name: Vacation Dresses & Outfits
Price: $36.90
Availability: In Stock
Available Color: MEDIUM, DENIM
Available Size: S, M, L, XL