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 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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Love's A Picnic Strapless Gingham A-Line Midi Dress
Be loved and admired by everyone who sees you in this gingham midi dress showcasing a flattering A-line silhouette with convenient side pockets to keep your hands warm!
Fit & Features
- Gingham print, woven fabric, tulle and woven linings
- Strapless neckline
- Back zipper closure, stretch smocked panel
- Side pockets
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3870
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Somewhere Tropical V-Neck Cutout Abstract Maxi Dress
This maxi dress plus you somewhere tropical equals the chicest vacation! The dress boasts a trendy cutout with a decor accent and a sultry side slit for effortless movement.
Fit & Features
- Abstract print, stretchy knit-lined fabric
- V-neckline with decor accent
- Spaghetti straps
- Cutout bodice, side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6055
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Season Of Bloom Flower Necklace And Earrings Set
It's the season of bloom with this ethereal flower necklace and earrings set! Perfect for adding a unique touch to your dressy look.
Fit & Features
- Necklace and earrings set
- Flower and leaf charm choker necklace, lobster clasp closure
- Flower stud earrings, post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07002-2126
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Babe Gingham Print Triangle Bikini Top
Channel that flirty babe style in this adorable gingham printed triangle bikini top with a dainty eyelet trim. Pair with the matching bikini bottoms for a sweet and sassy look.
Shop Matching Bottoms: Flirty Babe Gingham Print Side Tie Bikini Bottoms
Fit & Features
- Nylon-blend fabric, high stretch
- Gingham print
- Triangle design, eyelet trim
- Adjustable spaghetti straps
- Tie-back spaghetti straps
- Runs true to size
Style Number/Barcode: 07104-0717
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meet Downtown Retro Square Sunglasses
The perfect square sunglasses to slip on when you're heading out the door to give your outfit a retro-cute vibe!
Fit & Features
- Square design
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000030
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Full Schedule Sleek Oval Sunglasses
Look cool and trendy on the go in these sleek oval sunglasses for anything on your calendar!
Fit & Features
- Sleek oval design
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000023
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Palm Beach Straw Clutch
The perfect straw clutch with versatile styling options and space for your essentials!
Fit & Features
- Front flap closure
- Detachable chain strap
- Spacious interior
- Straw material
Style Number/Barcode: 07203-2114
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spill The Tea Oversized Square Sunglasses
Slip on these oversized square sunglasses on your way to spill the tea!
Fit & Features
- Oversized design
- Tinted square lenses
- 100% UV protection
Style Number/Barcode: 07008-000032
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Delightful Directions V-Neck Floral Ruffled Midi Dress
Make a charming impression in this floral midi dress showcasing a flowy ruffled silhouette and lace-up back that turns heads. Perfect for brunch, shower celebrations, and graduations!
Fit & Features
- Floral print, chiffon-lined fabric
- V-neckline, adjustable spaghetti straps
- Lace-up back
- Flowy ruffled silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3905
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Glamour Rhinestone Bee Charm Necklace
Sparkle with cute glamour in this dainty chain necklace with a sweet rhinestone bee charm.
Fit & Features
- Dainty chain
- Small bee charm
- Mini rhinestone embellishments
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-2137
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Attraction Cutout Bodycon Midi Dress
Look and feel like a babe in this bodycon midi dress with a flirty cutout twist back design and side slit for effortless movement! Pair with cute sandals.
Fit & Features
- Texture knit fabric, stretchy knit lining
- Scoop neckline, spaghetti straps
- Twist cutout back design
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2281
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Casual Babe Tinted Denim Overalls
The perfect pair of tinted denim overalls for a casual everyday vibe. Style with a graphic tee and sneakers.
Fit & Features
- Tinted denim fabric, no stretch
- Sleeveless square neckline, bib pocket
- Tank strap with adjustable buckles, racerback design
- Mid-rise waist, belt loops, buttoned sides
- Dual front and back pockets
- Straight-leg silhouette, relaxed fit
- Runs true to size
Style Number/Barcode: 06602-0574
Category Name: Vacation Looks
Price: $6.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Strolls High-Rise Gingham Capri Pants
Take a stylish stroll in these gingham capri pants while shopping downtown or a backyard bbq!
Fit & Features
- Gingham print, woven fabric
- High-rise waist
- Back zipper closure
- Form-hugging fit
- Side slit accents
- Capri-length hem
- Runs true to size
Style Number/Barcode: 06402-000002
Category Name: Vacation Looks
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Fling Corset Tie A-Line Midi Dress
Unleash your inner romantic in this midi dress at showers, graduations, or brunch! The tie bust corset bodice and lace-up back create a flattering silhouette, while the midi-length hem and textured fabric add a touch of playfulness.
Fit & Features
- Texture woven fabric, woven lining
- Sweetheart neckline, wide shoulder straps
- Dual tie front corset bodice, lace-up back
- Back zipper and hook-eye closure
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6068
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Modern Babe Sleeveless Belted Mini Dress
Take the city streets by storm in this sleeveless mini dress with a chic belted waist that cinches your look together from office hours to cocktail hour!
Fit & Features
- Woven fabric with stretch
- Crew neckline
- Back zipper and hook-eye closure
- Bodycon silhouette
- Dual faux leather belted waist
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5979
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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True Colors Open Back Abstract Satin Maxi Dress
A gorgeous satin maxi dress destined for dinner and drinks on vacay or the weekend. Designed with a sultry open back and a dreamy, flowy silhouette with dual slits for effortless movement.
Fit & Features
- Abstract print, satin fabric
- High neck with tie closure
- Open back
- Flowy silhouette
- Dual front slits
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000103
Category Name: Vacation Looks
Price: $19.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Vibe Tropical Floral Halter Maxi Dress
You'll be a total vibe on your summertime vacay in this tropical floral print maxi dress. The plunging halter neckline, ruched side seams, and curve-hugging fit are all alluring details you'll love.
Fit & Features
- Knit fabric with knit bust lining, high stretch
- Tropical floral print
- Sleeveless plunge V-neckline
- Tie-back halter straps, partially open back
- Ruched side seams
- Maxi-length hem, curve-hugging fit
- Runs true to size
Style Number/Barcode: 05102-6056
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breeze By Strapless Striped A-Line Midi Dress
Breeze by like a breath of fresh air in this striped midi dress! It's adorned with hidden side pockets to keep your hands warm and has a flattering A-line silhouette.
Fit & Features
- Striped print, woven fabric, woven lining
- Strapless neckline
- Stretchy smocked bodice
- Hidden side pockets
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6069
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Sleek Oversized Square Sunglasses
These trendy sleek oversized square-shaped sunglasses are the finishing touch to an everyday look that slays.
Fit & Features
- Oversized curved square-shaped design
- Thin brow bar
- Thin arms
- Rubber nose pads
- Tinted lenses
Style Number/Barcode: 07008-1130
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendsetter Leopard Print Oval Sunglasses
Show up looking like a chic trendsetter in these leopard print oval sunglasses perf for everyday wear.
Fit & Features
- Oval-shaped design
- Leopard printed frame
- Wide arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1131
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picture This Retro Rectangle Sunglasses
Enhance your style with these retro sunglasses for everyday looks! The sleek, rectangular design and tinted lenses create a timeless look that will elevate any outfit.
Fit & Features
- Rectangular design
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000020
Category Name: Vacation Looks
Price: $2.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Darling Halter Lace Skater Mini Dress
Twirl with bliss in this darling lace skater mini dress with a flirty halter neckline and open back. It's perfect for shower celebrations or a dressy date night!
Fit & Features
- Lace knit fabric, stretchy knit lining
- Halter V-neckline, tie closure
- Open back
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4157
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Its A Showdown Straw Cowboy Hat
Top off your Western vibe with this straw cowboy hat at festivals, concerts, or a bach trip!
Fit & Features
- Wide curved brim
- Straw material
- Adjustable inner strings for a snug fit
Style Number/Barcode: 07302-000033
Category Name: Vacation Looks
Price: $3.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce Attitude Leopard Sunglasses
Make a bold statement while protecting your eyes in these leopard sunglasses on sunny days!
Fit & Features
- Leopard print
- Sleek oval shaped frame
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000021
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free