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.
-
Summer Mode Espadrille Platform Wedge Heels
Capture the effortlessly chic vibe of the summer season with these espadrille platform wedge heels! They feature an open almond-shaped toe with a wide toe strap, a thin adjustable ankle strap with a buckle closure, a closed back with a woven design, and a tall platform wedge heel for a beachy boho look. Style with a pearl necklace and hoop earrings.
Fit & Features
- 5" Platform wedge heel
- Espadrille material
- Open almond toe, wide toe strap
- Thin adjustable ankle strap with buckle
- Closed back with woven design
- Faux leather luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-0347
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sultry Mood Cutout Bodycon Midi Dress
Boost your sultriness in this bodycon midi dress with a flirty cutout back and side slit giving effortless allure!
Fit & Features
- Textured knit stretchy fabric, sewn-in knit lining
- Scoop neckline
- Spaghetti straps
- Cutout back, twist straps
- Bodycon silhouette
- Side slit, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2292
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Gorgeous Allure Ruched Chiffon Bra Top
Radiate your gorgeous allure in this sultry ruched chiffon bra top! Designed with an airy sheer chiffon fabric with a front knit lining for coverage, this bra top is perfect for looking sunkissed this season. It features a sleeveless subtle sweetheart neckline, ruching at the bust with padding for support, and adjustable spaghetti straps for a customized fit. The smocked back design offers added stretch, while the ultra-cropped fitted hem creates a snatched silhouette. Complete the look with the matching palazzo pants!
Shop Matching Bottoms: Gorgeous Allure Chiffon Palazzo Pants
Fit & Features
- Sheer chiffon fabric, front knit lining
- Sweetheart neckline
- Ruched bust, padding
- Adjustable spaghetti straps
- Stretchy smocked back
- Ultra-cropped hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06003-2537
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunny Vibes Woven Wide-Leg Pants
These airy woven wide-leg pants will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric, they feature a flattering high-rise elasticized waist, front pockets, and a flowy wide-leg silhouette. Style with the matching crop top for a fabulous 'fit!
Shop Matching Top: Sunny Vibes Bow Back Woven Crop Top
Fit & Features
- Woven fabric with minimal stretch
- High-rise elasticized waistband
- Wide-leg fit
- Dual front pockets
- Runs true to size
Style Number/Barcode: 06402-1365
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cascading Romance Ruffle Floral Skater Dress
Get swept away into a world of romance in this floral skater dress perfect for a shower or date! The square neckline and tie-shoulder spaghetti straps add a touch of sweetness, while the stretchy smocked bodice ensures a comfortable fit. The skater silhouette and tiered ruffled hem make this dress perfect for twirling the night away. Complete the look with earrings.
Fit & Features
- Floral print, chiffon fabric with woven skirt lining
- Square neckline
- Tie-shoulder spaghetti straps
- Stretchy smocked bodice
- Skater silhouette with ruffles
- Runs true to size
Style Number/Barcode: 05101-2994
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Adorable Allure Puff Sleeve Tie-Back Crop Top
Showcase an adorable allure in the cutest puff sleeve crop top for casual summer parties! Designed with a stretchy knit fabric, it features a plunging V-neckline and short puff sleeves with elastic cinched hems. The trendy open back is accented with scrunched cross-back straps and lower tie-back straps for a customized fit, leading to a fitted cropped hem. Style with high-rise jeans and sneakers.
Fit & Features
- Stretchy double-lined knit fabric
- Plunge V-neckline
- Short puff sleeves
- Open back, cross-back straps, lower tie-back straps
- Fitted elasticized cropped hem
- Runs true to size
Style Number/Barcode: 06001-5186
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Country Babe Colored Stone Straw Cowboy Hat
A distressed cowboy hat featuring trendy colored stones along a string tie, perforated design, and a wide brim to help shade from the sun. Perfect for styling with cowboy boots.
Fit & Features
- Colored stones along the string tie
- Perforated design
- Wide brim
- Adjustable inner strings
- Distressed straw material
Style Number/Barcode: 07302-1641
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunny Daze Straw Crossbody Bag
Embrace sunnier days in this summer-ready straw crossbody bag featuring an adjustable chain-link strap, a top flap with snap closure, and a spacious lined interior with a single pocket. Complete the look in a cute bikini set for strolling the beaches.
Fit & Features
- Adjustable chain-link strap
- Straw material
- Top flap with snap closure
- Spacious lined interior with a pocket
Style Number/Barcode: 07203-1069
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Leafy Greens Charm Hoop Earrings
Eat your greens. Dress up your look in these dangle leaf charm earrings featuring a large sleek hoop and a fish hook with a rubber-back stopper for a secure fit. Style with a boho-inspired dress for the music festival season!
Fit & Features
- Dangling leaf charms
- Large sleek hoop
- Fishhook, rubber-back stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1281
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Hello Summer V-Cut Bikini Bottoms
Say hello to summer in these trendy bikini bottoms featuring a V-cut waist, scrunched detailing at the back, and a thong fit. Pair with the matching bikini top for a pool party.
Shop Matching Top: Hello Summer Triangle Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- V-cut waist
- Scrunched back
- Thong fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000011
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Summer Muse Linen Thong Wedges
These chic linen thong wedges will radiate bold summer vibes! Designed with a woven linen material, these heels are perfect for your getaway vacays. They feature a tall wedge heel for comfortable wear, a trendy square-shaped toe, a criss-cross thong strap design, and an open back for easy on-and-off styling. Pair with a flowy maxi dress and your fave shades.
Fit & Features
- 4.5" Wedge heel
- Open square toe
- Criss-cross thong strap design
- Open back
- Linen material, faux leather insole
- Runs true to size
Style Number/Barcode: 07406-0345
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flutter Some Hearts Butterfly Charm Earrings
You'll def flutter some hearts in these adorable butterfly charm earrings! Featuring a cascading drop design with rhinestone embellishments, these earrings couldn't get any more whimsical. Pair with a flirty skater dress and some sleek stilettos for your next party.
Fit & Features- Linear dainty drop design
- Rhinestone embellished butterfly charm
- Post back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.Style Number/Barcode: 07001-0435
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fashionable Good Time Espadrille Flat Sandals
Make sure to pack these espadrille flat sandals to ensure you have a fashionable good time on your next getaway! Featuring a closed round toe and adjustable ankle strap, these sandals offer a comfortable fit. The flat sole and cushioned faux leather insole make these shoes perfect for all-day wear. Complete the look with a trendy crossbody bag.
Fit & Features
- Closed round toe
- Adjustable ankle strap, buckle closure
- Flat sole
- Faux leather cushioned insole
- Espadrille material
- Runs true to size
Style Number/Barcode: 07405-0076
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Infinite Possibilities Tie Front Crop Top
Take the stress out of styling an outfit with this breezy crop top! Designed from a woven fabric, this top features adorable ruffled short sleeves and a flirty tie-front design that flaunts your figure along with the cropped hem. Complete the look with denim shorts and cute sandals!
Fit & Features
- Airy woven fabric, no stretch
- Ruffled short sleeves
- Tie-front closure
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1853
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Living My Best Life Satin Tie-Dye Tube Top
Ideal for sunny days, living your best life. This satin tie-dye tube top elevates your look with a sleek strapless neckline and pointed crop hem that flaunts your figure.
Fit & Features
- Tie-dye print, satin fabric, stretchy smocked back
- Strapless tube neckline
- Pointed crop hem
- Runs true to size
Style Number/Barcode: 06003-000042
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Tropical Day Dream High-Rise Wide Leg Pants
Look like a tropical day dream in these high-rise pants while on vacation! The elasticized waistband ensures a comfortable fit, while the wide-leg silhouette and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching top and skirt.
Shop Matching Top: Tropical Day Dream Tie-Front Crop Top
Shop Matching Skirt: Tropical Day Dream High-Rise Wrap Mini SkirtFit & Features
- Tropical print, stretchy knit fabric
- High-rise elasticized waistband
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2469
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Classic High-Rise Destructed Cut-Off Denim Shorts
Create the cutest summer 'fits with this classic pair of destructed cut-off denim shorts! Detailed with trendy distressed detailing on the medium-wash denim fabric, these jean shorts are the perfect casual staple. They feature a flattering high-rise waist, a fitted cut-off hem, a traditional five-pocket and belt loop design, and a secure front button and hidden zipper closure. Style with a crop top and strappy sandals.
Fit & Features
- Distressed denim fabric, moderate stretch
- High waist
- Fitted cut-off hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Runs true to size
Style Number/Barcode: 06603-0389
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Flutter Sleeve Tie-Front Eyelet Crop Top
Capture hearts with this flirty flutter sleeve tie-front crop top! Designed with a lightweight woven fabric, it features a ruffled V-neckline with short flutter sleeves, a tie-front design for a stylishly cinched silhouette, a partial low back, and a cropped hem with an adorable eyelet trim. Complete the look with denim shorts and sandals.
Fit & Features
- Textured woven fabric, sewn-in knit lining
- Ruffled V-neckline
- Short flutter sleeves
- Tie-front cinched silhouette
- Partial low back
- Cropped hem with eyelet trim
- Runs true to size
Style Number/Barcode: 06003-2581
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Hello Summer Triangle Bikini Top
Say hello to summer in this trendy bikini top featuring triangle-shaped cups with removable padding and dual spaghetti strap ties that let you customize the style. Pair with the matching bikini bottoms for a pool party.
Shop Matching Bottoms: Hello Summer V-Cut Bikini Bottoms
Fit & Features
- Nylon-blend fabric, high stretch
- Triangle design
- Removable padding
- Dual tie-back halter straps
- Lower tie-back straps
- Runs true to size
Style Number/Barcode: 07104-000008
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Exotic Vibes Strapless Tie-Front Tropical Romper
You'll be looking exotic and beautiful in this tropical romper on vacation or by the pool! Featuring a flattering strapless sweetheart neckline and tie-front bust, this romper also offers a comfortable and stylish fit with its stretchy smocked back with cutout and a flowy short-length hem. Complete the look with a layered necklace and strappy sandals.
Fit & Features
- Tropical print, woven fabric lined with stretchy knit
- Strapless sweetheart neckline
- Tie-front bust
- Smocked back with cutout
- Flowy short-length hem
- Runs true to size
Style Number/Barcode: 06403-0427
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweet Talker Strappy Back Halter Skater Mini Dress
Sweeten any room with your vibe in this halter skater dress, which flaunts a strappy open back that turns heads with every wear!
Fit & Features
- Woven fabric, stretchy knit lining
- Halter V-neckline with spaghetti strap tie
- Open back with tie-back detail
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6029
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sway With The Palm Print Mesh Duster
Sway with the breeze in this palm print mesh duster to layer over your chic vacation or pool party look! The duster has fitted long sleeves and an open front design giving everyone a peek at your cute self, and a flowy longline hem. Complete the look in flat sandals and sunnies!
Fit & Features
- Palm print
- Stretchy sheer mesh fabric
- Long fitted sleeves
- Flowy longline hem
- Runs true to size
Style Number/Barcode: 06202-0445
Category Name: Vacation Looks
Price: $16.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sky Gazing Moon Star Chain Belt
Adorn yourself with celestial style with this moon star chain belt perfect for skygazers and dreamers! Featuring charming moon and star charms and a secure lobster clasp closure, this chain belt adds a touch of magic to any outfit. Complete the look in a trendy denim romper for a festival, concert, or night at the fair!
Fit & Features
- Moon and star charms
- Chain belt
- Lobster clasp closure
Style Number/Barcode: 07301-1109
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Safari Babe Zebra Rhinestone Faux Suede Cowboy Hat
Look and feel like a total safari babe in this zebra cowboy hat! This hat is made from soft faux suede and features a curved wide brim to help protect from the sun and an inner adjustable string for a snug fit. The rhinestone embellished trim and cord with adjustable toggle add a touch of glamorous detail. Complete the look in a flirty romper and boots for a jungle adventure!
Fit & Features
- Zebra print
- Curved wide brim
- Rhinestone embellished trim and cord with adjustable toggle
- Inner adjustable strings
- Faux suede material
Style Number/Barcode: 07302-1638
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale