Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Looks
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Sweet Existence High-Rise Bow Mini Ruffle Skort
Step out wearing this pointelle mini skort for a sweet look on any sunny day! Features a high-rise waist with delicate lace trim and a charming bow, creating a flattering and feminine silhouette. The bodycon fit hugs your curves while the layered ruffled mini-length hem adds a playful touch. Complete the look in a flirty crop top and sneakers for casual plans!
Fit & Features
- Pointelle knit fabric, shorts lining
- High-rise waist, lace trim and bow
- Bodycon fit
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06503-1197
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sassy Sweet Floral Strapless Mini Dress
This sassy sweet strapless mini dress was made for a vacay or weekend getaway! Designed with an abstract floral print, it features side ruching leading to a chic short slit and a flowy A-line silhouette.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract floral print
- Strapless straight neckline
- Side ruching, adjustable tie, short side slit
- Mini-length A-line silhouette, asymmetric hem
- Runs true to size
Style Number/Barcode: 05103-000094
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect In Paradise Floral One-Piece Swimsuit
Create a poolside look perfect for paradise in this one-piece swimsuit featuring a large floral print, a halter neckline with an alluring bust cutout, and a cheeky fit. Style with gold bangle bracelets and flat sandals.
Fit & Features
- Nylon-blend fabric, high stretch
- Large floral print
- Halter neckline, large bust cutout
- Tie-back halter straps, open lower back
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000013
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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New Favorite Thong Strap Low-Block Heels
These simple yet stylish low-block heels will become your new fave go-to! Made with sleek faux leather material, they feature an open square-shaped toe with a thin thong strap design, thin adjustable ankle and heel straps for a customized fit, and a low block heel for comfort and a chic look. Pair with a mini handbag for your weekend plans!
Fit & Features
- 3" Low block heel
- Faux leather upper
- Square toe
- Thong strap design
- Adjustable ankle and heel straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4664
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Personality Button Up Crop Linen Shacket
An easygoing babe like you will appreciate this linen shacket for effortless styling! Featuring three quarter roll cuffed sleeves, a collar neckline, and button-up front closure, this shacket brings versatility to your wardrobe. With flap pockets and a cropped hem, this shacket adds a playful touch to any outfit. Complete the look in trendy boots.
Fit & Features
- Linen blend woven fabric, no stretch
- Collar neckline
- Button up front closures
- Flap pockets
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1784
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Step Into Summer Linen Wooden Platform Heels
Step into summer looking fabulous in these platform heels! These block heels feature a square toe with a wide strap, an adjustable ankle strap with buckle closure, and a lightweight wooden platform sole for a trendy finish. Complete the look with a cute handbag.
Fit & Features
- 3.5" Block Heel
- Square toe
- Adjustable ankle strap, buckle closure
- Lightweight wooden platform sole
- Luxe fit cushioned insole
- Linen material
- Runs true to size
Style Number/Barcode: 07401-4886
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destined For Sun Tropical Mesh Tie Front Top
This tropical sheer mesh top is destined to go with you on the next sunny getaway! Featuring long sleeves with cuffs, a tie-front design, and a cropped hem to highlight your curves. Complete the look with the matching bottoms.
Shop The Matching Bottoms: Destined For Sun Tropical Mesh Mini Skirt
Fit & Features
- Tropical palm print, sheer mesh fabric, moderate stretch
- Long sleeves with cuffs
- Tie-front design
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-0452
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Chic Cutout Sandals
Bringing effortless energy wherever you go. These chic slide sandals are your no-brainer pick for sun-soaked strolls, coffee runs, and last-minute plans.
Fit & Features
- Square toe
- H-shaped band
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000038
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- Sale
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Cute Trek Strappy Lace-Up Flat Sandals
Your trek to the farmer's market is looking cute in these statement flat sandals! They feature a square toe, a caged strappy design with knotted accents, and a trendy lace-up ankle that lets you customize the style on faux leather material. Complete the look with a trendy handbag.
Fit & Features
- Flat sole
- Square toe
- Strappy caged design with knotted accents
- Lace-up ankle
- Lightly cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1155
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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First Day Of Spring Puff Sleeve Smocked Romper
Embrace the beauty of spring in this adorable romper! Featuring delicate puff short sleeves and a tie-front bust, this romper flatters everyone. The stretchy smocked waist and flowy short-length hem provide ultimate comfort and style. Complete the look in cute sandals and sunnies for any casual outing!
Fit & Features
- Woven fabric lined with stretchy knit
- Tie-front bust
- Stretchy smocked waist
- Runs true to size
Style Number/Barcode: 06303-0265
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Allure Chiffon Palazzo Pants
Radiate your gorgeous allure in these chic chiffon palazzo pants! Designed with an airy sheer chiffon fabric with a lightweight woven lining for coverage, these pants are perfect for the summer season. They feature a high-rise fit with a stretchy elastic waistband and a relaxed wide-leg silhouette for style and comfort. Complete the look with the matching bra top!
Shop Matching Top: Gorgeous Allure Ruched Chiffon Bra Top
Fit & Features
- Sheer chiffon fabric, woven lining, no stretch
- High waist, elastic waistband
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06402-1413
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sea Worthy Shell Charm Hoop Earrings
From pool parties to beach bashes, these shell charm hoop earrings bring all the summery vibes! Complete the look with cute sandals.
Fit & Features
- Hoop earrings
- Paperclip chain-link design
- Shell charms
- Hook closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2014
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set For Cuteness Twist Back Slit Rib Knit Maxi Dress
You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!
Fit & Features
- Stretchy rib knit fabric
- Square neckline
- Shoulder straps
- Twist back design
- High side slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5577
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Down For Anything Buckle Criss-Cross Sandals
With these trendy buckle criss-cross sandals you'll be down for any last minute plans that involve showing them off!
Fit & Features
- Square toe
- Buckle criss-cross straps
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1259
Category Name: Vacation Looks
Price: $8.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Life's A Breeze Floral Cutout Midi Dress
This floral cutout maxi dress makes getting ready a breeze! It features short puff sleeves, a ruched sweetheart bodice with a flirty waist cutout that leads to a flowy, maxi silhouette with a slit accent. Composed of a chiffon-lined fabric with no stretch. Style with a trendy mini tote.
Fit & Features
- Short puff sleeves
- Ruched sweetheart bust
- Waist cutout, smocked back
- Maxi silhouette with slit accent
- Floral pattern
- Chiffon fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-3193
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Endless Vacay Strapless Tube Crop Top
Get ready for vacay packing this tube top for endless fun under the sun! Whether you're island hopping in Greece or sipping a mai tai on the beach, this crop top will keep you so trendy. It boasts a strapless neckline with a non-slip grip lining for a secure fit, a stretchy smocked back for easy on-and-off styling, plus a cinched front that adds a flirty touch. Complete the look with the matching bottoms.
Shop Matching Bottoms: Endless Vacay High Rise Wide-Leg Trouser Pants
Fit & Features
- Texture woven fabric, partial sewn-in knit lining
- Stretchy smocked back
- Non-slip grip lining
- Cinched front
- Ultra-cropped length
- Runs true to size
Style Number/Barcode: 06003-2528
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destined For Sun Tropical Mesh Mini Skirt
This tropical mesh mini skirt is destined to go with you on the next sunny getaway! Featuring a high-rise waist, a bodycon silhouette with a wrap accent to highlight your curves and a mini-length hem. Complete the look with the matching top.
Shop The Matching Top: Destined For Sun Tropical Mesh Tie Front Top
Fit & Features
- Tropical palm print, sheer mesh fabric, moderate stretch
- Long sleeves with cuffs
- Tie-front design
- Cropped hem
- Runs true to size
Style Number/Barcode: 06501-0979
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Radiant Accent Floral Boho Satin Scarf
The perfect satin scarf to give your outfit a radiant accent! The silky satin woven material is designed with a vibrant floral bohemian-inspired print for a trendy allure. Style this scarf as a pretty headwrap, around your neck, or tied on your bag as a chic accent! Complete the look with a sleek choker necklace.
Fit & Features
- Silky satin woven material
- Floral bohemian print
- Multiple ways to style and wear
Style Number/Barcode: 07305-0495
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Go Jacquard Woven Tote Bag
Grab your essentials and you'll be ready for any plans with this jacquard woven tote bag! Perfect for vacation, beach days, or daytime outings, this tote bag features top handles and a spacious interior with a zipper pocket and two slot pockets convenient for your cash, cards, keys, and phone. Complete the look with sunglasses and sandals!
Fit & Features
- Top handles
- Spacious interior, zipper pocket, two slot pockets
- Jacquard woven material
Style Number/Barcode: 07203-2024
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trend Factor Angled Oval Sunglasses
Level up the trend factor of your summer looks with these cool shades. The sunglasses feature an angled oval-shaped design with a translucent plastic frame, built-in nose pads, and tinted lenses. Pair with a charm necklace and sneakers.
Fit & Features
- Angled oval-shaped design
- Translucent plastic frame
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1088
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Butterfly Baby Layered Chain Belt
Upgrade your style with this butterfly layered chain belt! This trendy belt features layered chains and adorable butterfly charms for a fun and playful look and a secure lobster clasp closure. Complete the look in a basic bodycon midi dress and heels for a concert or dinner out with the girls!
Fit & Features
- Layered chain design
- Butterfly charms
- Lobster clasp closure
Style Number/Barcode: 07301-0710
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wifey Material Scoop Neck Tank Crop Top
From the bachelorette bash to the big day, this tank crop top will channel those wife vibes! The top boasts a flattering scoop neckline and shoulder straps, a front embroidery with the words, "Wifey Material", and a flirty fitted crop hem on rib knit fabric. Complete the look in a white mini skirt and sneakers!
Fit & Features
- Rib knit fabric, minimal stretch
- Scoop neckline
- Shoulder straps
- front embroidery with the words, "Wifey Material"
- Cropped hem
- Runs true to size
Style Number/Barcode: 06002-1846
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Chic Woven Cabby Hat
Elevate your casual 'fits with this lightweight woven cabby hat! It features a classic cabby design with a short curved brim and side button accents. Includes adjustable ties hidden on the inside for a tighter fit. Style with ankle booties for a chic vibe.
Fit & Features
- Woven fabric
- Classic cabby design
- Short curved brim
- Side buttons
- Adjustable ties for tighter fit
Style Number/Barcode: 07302-1623
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Festive Fun Strapless Striped Bandeau Crop Top
Weekend activities just got a little cuter in this striped bandeau crop top perfect for vacations or going to a summer fair! The strapless sweetheart neckline and tie front bust create a comfortable and flattering fit, while the ultra-cropped hem and striped print bring a stylish touch. Complete the look with the matching bottoms.
Shop The Matching Bottoms: Festive Fun High-Rise Striped Palazzo Pants
Fit & Features
- Striped print, woven lined fabric
- Strapless sweetheart neckline
- Stretchy smocked back
- Tie front bust design
- Padded bra cups
- Ultra-cropped length
- Runs true to size
Style Number/Barcode: 06003-2561
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale