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.
Now Trending
STYLE SPOTLIGHT
Get Eye-Catching Sandals For Women
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.
-
Feeling Peachy Graphic Tube Top
Made for sunny day dressing, this graphic tube top showcases a front peach and graphic detailing that creates boldly cute looks!
Fit & Features
- Stretchy knit fabric
- Strapless neckline
- Peach and graphic detailing
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000035
Category Name: Vacation Looks
Price: $22.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Made For Struts Over The Knee Boots
Made for stylish strutting down the street, you'll adore these faux leather over-the-knee boots featuring an almond toe, a stacked block heel, a side zipper closure, and a high shaft. Complete the look in a trendy sweater dress for a day in the city!
Fit & Features
- Almond toe
- Stacked block heel
- Side zipper closure
- High shaft, over the knee
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0843
Category Name: Vacation Looks
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sleek Strut Knee-High Boots
This fall season, strut with style in these sleek knee-high boots! They feature a pointed toe, a sturdy block heel, an inner zipper closure, and a fitted shaft. Pair these faux leather boots with your favorite sweater dress.
Fit & Features
- Knee-high length
- Pointed toe
- Block heel
- Inner zipper closure
- Fitted shaft
- PU material, smooth lining
- Runs true to size
Style Number/Barcode: 07402-0793
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fleece Shaper Leggings
Comfy and flattering, these fleece leggings are perfect for lounging, traveling, and the office! They feature a high-waist fit with tummy control to smooth and shape your figure. These fleece-lined leggings will keep you cozy while appearing incredibly chic paired with an elevated crop top and tailored blazer or moto jacket for a fierce #OOTD look.
Fit & Features
- Tummy control waistband
- Skinny leg fit
- Cozy fleece-lined knit fabric
- Moderate stretch
- Sizes run small
Style Number/Barcode: 06502-1228
Category Name: Vacation Looks
Price: $6.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Stylish Staple Henley Crop Top
This on-trend henley crop top is a stylish staple to add to your cart! It features a scoop neckline with a plunging notched front design, sleek metal grommet accents, long fitted sleeves, a fitted cropped hem, and a lower back cutout with a criss-cross strap design. Pair this ribbed knit top with cargo pants and mules.
Fit & Features
- Scoop neckline, plunging notched front design
- Metal grommet accents
- Long fitted sleeves
- Fitted cropped hem
- Lower back cutout, criss-cross strap design
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1495
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Take Me Away High-Rise Palazzo Pants
These statement palazzo pants are ready to be whisked off on your next adventure! Made from linen-like cotton fabric, these pants offer a comfortable high-rise drawstring waist, convenient side pockets, and a flowy, wide-leg for stylish flair.
Fit & Features
- Linen-like cotton woven fabric
- High-rise elasticized drawstring waist
- Side pockets
- Flowy, wide-leg fit with seam details
- Runs true to size
Style Number/Barcode: 06302-000010
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Festive Fun High-Rise Striped Palazzo Pants
Weekend activities just got a little cuter in these striped palazzo pants perfect for vacations or going to a summer fair! The high-rise elasticized waistband and pleating create a comfortable and flattering fit, while the wide-leg flowy silhouette and striped print bring a stylish touch. Complete the look with the matching top
Shop The Matching Top: Festive Fun Strapless Striped Bandeau Crop Top
Fit & Features
- Striped print, woven fabric
- High-rise elasticized waistband with pleating
- Wide-leg flowy silhouette
- Runs true to size
Style Number/Barcode: 06402-1424
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Effortless Enchantment Floral Pleated Maxi Dress
This floral maxi dress brings the effortless, enchanted vibes to any occasion! With a sweetheart neckline and a pleated, flowy silhouette, you'll adore this dress all season long.
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline
- Adjustable spaghetti straps
- Tie-back detail, lower hidden zipper and hook-eye closure
- Pleated flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3914
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Serving Shade Square Oversized Sunglasses
These oversized square sunglasses with tinted lenses = instant it-girl upgrade!
Fit & Features
- Oversized square frames
- Tinted 100% UV protection lenses
- Smooth plastic frame with luxe finish
Style Number/Barcode: 07008-000007
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cozy Prep Collared Sweater
Cozy on up this fall while still keeping your look preppy with this cute collared sweater. It features a V-neckline with a trendy polo collar, long dolman-style sleeves, and a mid-length, relaxed fit. The soft ribbed knit fabric offers a moderate stretch for comfortable wear. Style this sweater with dark wash denim and booties.
Fit & Features
- V-neckline
- Polo collar
- Long dolman sleeves, tapered hems
- Mid-length, relaxed fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1300
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Destination Dinner V-Neck Midi Dress
Look fabulous in a flash wearing this sleeveless midi dress for dinner and drinks! It features a showstopping bodycon silhouette, a V-neck, tank straps, and side ruched seams that hug every curve like a glove. Complete the look with chic stiletto heels.
Fit & Features
- Sleeveless, V-neck, tank straps
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Slinky knit fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4834
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunny Oasis Halter Crop Top
Escape to a sunny destination with this alluring halter cowl crop top! Pair with the matching skirt to complete the trendy vibe.
Fit & Features
- Slinky knit stretchy fabric
- Halter cowl neckline, tie closure
- Side ruched seams
- Crop hem
- Runs true to size
Shop The Matching Skirt: Sunny Oasis Ruffle Mini Skirt
Style Number/Barcode: 06001-000145
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Slinky Knit Wrap Front Top
The perf dressy top to take you from the office to happy hour. It features bishop long sleeves, a plunge V-neckline, and a wrap-style bodice, with tie-front detail along the cropped hem. Complete your look with high-rise pants and heels.
Fit & Features
- Bishop long sleeves
- Plunge V-neckline
- Wrap-style bodice
- Tie-front detail, crop hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06001-4708
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Getaway Retreat Sweetheart Tropical Crop Top
Getaway in this tropical crop top for the sweetest vacay vibe! This crop top features wide shoulder straps, a sweetheart neckline for a flattering look, padded bra cups for support, and a stretchy smocked back and cropped hem to flaunt your figure. Complete the look with the matching bottoms.
Shop The Matching Bottoms: Getaway Retreat High Rise Tropical Pants
Fit & Features
- Tropical print, woven fabric, sewn-in lining
- Wide shoulder straps
- Sweetheart neckline
- Padded bra cups
- Stretchy smocked back
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2504
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Little Miss Charming Strappy Back Denim Romper
Turn heads with your charm in this denim romper at concerts or weekend fun! Designed with a strappy open back, side pockets, and a pleated short hem, this romper is both stylish and functional.
Fit & Features
- Denim fabric
- Halter V-neckline, keyhole cutout
- Strappy open back, zipper closure
- Side pockets
- Pleated short hem
- Runs true to size
Style Number/Barcode: 06603-000008
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Chic Flowy Chiffon Midi Dress
Get the perf semi-formal look in this effortlessly chic chiffon midi dress. It features a sleeveless sweetheart neckline with a padded bust, spaghetti straps, a flattering high waist seam, and a mid-length skirt with a front slit and a flowy A-line silhouette. Style this dress with sleek earrings and cute heels.
Fit & Features
- Sleeveless sweetheart neckline
- Built-in padded bust
- Adjustable spaghetti straps
- Partially smocked back, zipper and hook-eye closure
- High waist seam, flowy A-line silhouette, front slit
- Sheer chiffon fabric, inner knit lining
- Runs true to size
Style Number/Barcode: 05101-2187
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Style Ruched Romper
Show off your flirty style in this adorable romper! Designed with a stretchy smooth knit fabric, it features a sweetheart neckline, short puff sleeves that can be worn off-the-shoulder, ruched detailing at the waist, a fit and flare silhouette, and flowy shorts with a mini skirt overlay. Complete the look with gold hoops and strappy sandals.
Fit & Features
- Smooth knit fabric, plenty of stretch
- Sweetheart neckline
- Short puff sleeves, elastic cinched hems
- Ruching at the waist, elastic seams
- Fit and flare silhouette
- Flowy shorts, mini skirt overlay
- Runs true to size
Style Number/Barcode: 06503-0987
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Weekend Fun Ruffled Mini Skort
This adorable mini skort was made for weekend fun, designed with a tiered ruffled mini-length overlay over hidden shorts. Style with the matching tie-front top for the cutest vibe.
Shop Matching Top: Weekend Fun Flutter Sleeve Tie-Front Top
Fit & Features
- Cotton woven fabric with swiss dot pattern, no stretch
- Mid-rise elasticized waist
- Tie-front adjustable drawstring
- Tiered ruffled design
- Mini-length overlay, A-line silhouette
- Hidden fitted knit shorts, moderate stretch
- Runs true to size
Style Number/Barcode: 06303-000013
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Free Spirit Chick High-Rise Boho Flare Pants
These boho pants are for the free-spirit chicks who want to look trendy during festivals, concerts, or at parties! Made from a soft brushed knit stretchy fabric with a bohemian-inspired print, they feature a flattering high-rise elasticized waist for comfort, a hip-hugging fit, and a flared hem. Style with a cute crop top!
Fit & Features
- Bohemian-inspired print
- Brushed knit stretchy fabric
- Hip-hugging fit
- Flared hem
- Runs true to size
Style Number/Barcode: 06502-2459
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Inspired Art Abstract Bodycon Mini Dress
Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments!
Fit & Features
- Abstract print, mesh-lined fabric
- Adjustable spaghetti straps
- Square neckline, padded bra cups
- Front ruched drawstring
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-5952
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Coastal Destination Halter Tie-Front Crop Top
Go bold in this halter crop top designed to bring an alluring look with a center slit and string tie-front. Perfect for coastal vacays!
Fit & Features
- Texture knit fabric, bust knit lining
- Halter plunge V-neckline, spaghetti strap tie
- String tie-front with beaded ends
- Center slit design
- Crop hem
- Runs true to size
Style Number/Barcode: 06003-000032
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Perfect Style Faux Leather Platform Block Heels
These on-trend platform block heels are the perfect style for elevating your look! Designed with smooth faux leather material, they feature a chunky block heel for comfortable wear, an open almond-shaped toe with a wide criss-cross strap design, thin adjustable ankle and heel straps with a buckle closure, and a tall platform sole for that added height. Pair with a flowy sundress for a weekend party!
Fit & Features
- 4.5" Chunky block heel
- Faux leather upper, padded insole
- Open almond toe
- Criss-cross strap design
- Adjustable ankle and heel straps with buckle closure
- Platform sole
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4670
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Clean Lines Scoop Neck Seamless Top
This minimalistic basic top is what every girl needs for everyday styling! The crop top features long fitted sleeves, and a scoop neck, and is composed of a buttery soft knit fabric with a seamless design. Complete the look in a cute jean jacket, paper bag pants, and booties!
Fit & Features
- Long fitted sleeves
- Scoop neck
- Cropped hem
- Buttery soft knit fabric, seamless design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1534
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Luxury Cowl Neck Marble Glitter Mini Dress
Indulge in the flirty luxury of this mesh mini dress for a night on the town! Crafted from an airy mesh fabric adorned with a glam marble print with glitter streaks, this dress is ready to be the most divine at the club. Featuring a sultry cowl neckline, adjustable spaghetti straps for a custom fit, and side ruched seams along the bodycon silhouette that flaunts your figure! Complete the look with platform heels.
Fit & Features
- Marble print, glitter streaks
- Mesh fabric, sewn-in knit lining with stretch
- Adjustable spaghetti straps
- Side ruching
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5432
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale