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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Summer Vacation Dresses & Outfits Ready For Fun!
Get ready for your next getaway with Windsor's stunning vacation dresses and outfits that blend style and confidence. Perfect for beach resorts or lake retreats, our versatile ensembles, including matching sets and trendy pieces like crop tops and linen pants, make vacation styling effortless. Layer with lightweight sweaters or tie-front tops to transition your look from day to night seamlessly. Embrace bold colors and romantic prints for dinners under the stars, and complete your chic vacation look with statement accessories like espadrille wedges and crossbody bags. Explore Windsor's collection in-store or online to make packing for your 2024 adventures a breeze.
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Romance That Wows Large Blossom Floral Maxi Dress
Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!
Fit & Features
- Large blossoming floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3343
Category Name: Vacation Dresses & Outfits
Price: $45.90
Availability: In Stock
Available Color: BLACK, BLACK-2
Available Size: S, M, XS
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Cute Sight Cateye Metal Sunglasses
This pair of sunglasses features a cateye design on a sleek metal frame, tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.
Fit & Features
- Cateye design, sleek metal frame
- Tinted lenses
- 100% UV protection
- Rubber nose supports
Style Number/Barcode: 07008-1105
Category Name: Vacation Dresses & Outfits
Price: $10.90
Availability: In Stock
Available Color: IVORY
Available Size: NS
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Sweet One Off-The-Shoulder Crop Top
Show off your sweet side in this off-the-shoulder crop top perfect for summer fun! Features a sweetheart neckline and short sleeve cuffs for a flattering fit. The adjustable drawstring allows for a customizable look and the cropped hem adds a touch of trendiness. Complete the look in denim shorts and sandals for a day out!
Fit & Features
- Stretchy rib knit fabric
- Off-the-shoulder, sweetheart neckline
- Adjustable drawstring
- Cropped length
- Runs true to size
Style Number/Barcode: 06002-1865
Category Name: Vacation Dresses & Outfits
Price: $22.90
Availability: In Stock
Available Color: WHITE, YELLOW, PINK
Available Size: XS, S, M, L
Product Badge:- Sale
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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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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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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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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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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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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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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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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
Product Badge:- New Arrival
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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
Product Badge:- New Arrival
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Covetable Charm Strapless Mini Skater Dress
From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.
Fit & Features
- Poplin stretchy fabric, sewn-in knit lining
- Back zipper and hook-eye closure
- Strapless square neckline
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3082
Category Name: Vacation Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: WHITE, SAGE, DENIM
Available Size: S, M, L
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Blooming Beauty Floral Print Mesh Maxi Dress
Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels!
Fit & Features
- Mesh fabrication
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Floral print
- Bodycon-like fit
- Long maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3785
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L, XL
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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
Available Size: XS, S, M, L, XL
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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, S, M, L
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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
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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: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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All The Splendor A-Line Faux Pearl Lace Mini Dress
Look and feel gorgeous in this lace A-line mini dress at parties and showers! This playful mini dress features a flattering V-neckline, spaghetti straps, and a lace-up back for the perfect fit. The A-line silhouette and faux pearl embellishments add a touch of whimsy to this lacey ensemble! Complete the look in block heels and a clutch.
Fit & Features
- Faux pearl embellishments
- Lace fabric lined with stretchy knit
- Spagehtti straps
- V-neckline
- Lace-up back, zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3018
Category Name: Vacation Dresses & Outfits
Price: $49.90
Availability: In Stock
Available Color: LAVENDER
Available Size: S, M, L
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What You Want Strappy Cutout Slit Midi Dress
This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!
Fit & Features
- Double-lined rib knit fabric, moderate stretch
- Spaghetti straps
- Square neckline
- Strappy cutout twist back
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5663
Category Name: Vacation Dresses & Outfits
Price: $36.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: XS, S, M, L
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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: XS, S, M, L