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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Playfully Perfect High Rise Slit Mini Denim Skirt
This mini denim skirt is playfully perfect for every casual social plan on your radar! With a high-rise waist and curve-enhancing seams along the bodycon silhouette, this skirt flatters your figure. Plus, the dual front slits add a flirty touch while the mini-length hem keeps things playful. Complete the look in a cute tee and sneakers.
Fit & Features
- Medium-wash denim fabric, no stretch
- High-rise waist
- Bodycon silhouette
- Five-pocket styling, front button closure
- Hidden zipper closure
- Runs true to size
Style Number/Barcode: 06601-0197
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Under The Sun Tropical Flower Hair Comb
Enjoy the island under the sun adorning your tresses with this beautiful tropical flower hair comb! Complete the look in a matching set and sandals.
Fit & Features
- Tropical flower hair comb
Style Number/Barcode: 07006-0469
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fun Favorite High Rise Distressed Denim Shorts
Grab your bestie and throw on these denim shorts for a fun summer adventure! Made from a medium wash fabric with a cool vintage-inspired color fading, these jean shorts will be essential all season. They feature a flattering high-rise waist, distressed accents for a major trend factor, and an edgy cut-off hem. Complete the look in a cute crop top and sandals!
Fit & Features
- Medium wash denim, color fading effect
- High rise waist
- Distressed accents, cut off hem
- Front button and hidden zipper closure
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-0395
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top
Sweet and flirty, this flutter-sleeve floral tie-front top will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The top features a V-neckline with a tie-front design, short flutter sleeves for a feminine touch, and a cropped hem with a relaxed fit. Style with the matching mini skirt for a day date!
Shop Matching Bottoms: Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt
Fit & Features
- Ditsy floral printed knit fabric, moderate stretch
- V-neckline with tie-front design
- Short flutter sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06202-0464
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Look Ruffled Cutout Woven Maxi Dress
Create a breezy-chic look with this woven maxi dress that will prove to be a summer staple! Designed with a lightweight woven fabric accented with ruffled trims, the long dress features a sleeveless square neckline with a keyhole cutout and tie-front detail, adjustable spaghetti straps for a customized fit, and dual cutouts at the stretchy smocked waist that lead to an open lower back. The tiered flowy A-line silhouette will give you an effortlessly pretty look. Style with strappy sandals.
Fit & Features
- Woven fabric, ruffled trims, short knit stretchy lining
- Square neckline, keyhole cutout with tie-front
- Adjustable spaghetti straps
- Stretchy smocked waist
- Dual cutouts leading to open lower back
- Tiered flowy A-line fit
- Runs true to size
Style Number/Barcode: 05102-5729
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Dreams Halter V-Neck Boho Chiffon Maxi Dress
Summer dreams are made of this boho chiffon maxi dress perfect for your vacation or weekend getaway! The halter V-neckline and spaghetti strap tassel ties provide an effortlessly chic touch, while the stretchy smocked bodice and hidden side pockets offer convenience. The flowy ruffled silhouette adds a touch of romance! Complete the look in sandals and a bracelet.
Fit & Features
- Bohemian print, chiffon fabric with woven lining, no stretch
- Halter V-neckline
- Spaghetti strap tassel ties
- Stretchy smocked bodice
- Hidden side pockets
- Flowy ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5777
Category Name: Vacation Looks
Price: $6.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feel The Vibes Halter V-Neck Crop Top
Get ready to feel the vibes of this elevated basic halter V-neck crop top! It's perfect for styling with any bottoms.
Fit & Features
- Smooth knit, cotton-blend, stretchy fabric
- Halter V-neck
- Crop hem
- Runs true to size
Style Number/Barcode: 06002-000206
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: GREEN, TEAL, LIME, BROWN-2, OLIVE
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Spring Breeze Sweetheart Tie Eyelet Crop Top
Spring into the new season in this eyelet crop top for vacations or weekend fun! Featuring a playful sweetheart neckline and delicate spaghetti straps, this top will keep you feeling cool and confident. The tie front adds a touch of charm, while the cropped hem and eyelet lace fabric offer a romantic and airy look. Complete the look with the matching bottoms.
Shop Matching Bottoms: Spring Breeze Ruffled Eyelet Maxi Skirt
Fit & Features
- Eyelet lace fabric, slight stretch
- Spaghetti straps
- Tie front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5282
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On Trend Layered Bead Necklace
Achieve an on trend look with this layered necklace featuring colored beads that give your outfit a refreshing update! Complete the look with sandals.
Fit & Features
- Layered design
- Colored beads
- Lobster clasp closure
Style Number/Barcode: 07002-1861
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hey Shorty High-Rise Cut Off Denim Shorts
Hey, shorty looking cute in these high-rise denim shorts! Perfect for any spring or summer plans, these shorts fit just the way you want and flatter from every angle. The high-rise waist and form-hugging fit hug your figure, while the distressed accents and cut-off hem add a touch of edgy style. Complete the look in a flirty crop top.
Fit & Features
- Denim fabric with stretch
- High-rise waist, hidden front button and zipper closure
- Distressed accents, five-pocket styling
- Cut off hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0378
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Vacay High Slit Tropical Mesh Midi Dress
Dare to allure on your next vacay in this sultry high slit tropical midi dress! The airy-lined mesh fabric is detailed with a bold all-over tropical palm leaf print to bring those dreamy destination vibes to your look. The mid-length dress features a sleeveless square neckline with pleating, spaghetti straps that lead to an open cross-back strappy design, a high-cut side slit to show off some leg, and a slim-fit silhouette to flaunt your figure. Style with hoop earrings and sandals for a beachy-chic outfit.
Fit & Features
- Tropical print
- Stretchy mesh fabric with knit lining
- Square neckline
- Spaghetti straps, open cross-back strappy design
- High side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5688
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wanderlust Mode Wide-Leg Pants
Crush your style game in these wide-leg pants. With a smooth knit and flared hem, these pants bring effortless chic to your every move. Perfect for your next adventure!
Shop Matching Top: Wanderlust Mode Cutout Tube Top
Fit & Features
- Smooth knit fabrication with stretchy knit lining
- Mid-rise waist
- Straight-leg fit
- Flared wide-leg hem
- Pants in size small have an 11" front rise with a 28" inseam
- Runs true to size
Style Number/Barcode: 06502-2569
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stars Align Filigree Earrings
The stars have aligned and these earrings belong in your jewelry box. They feature a metal filigree design and a rubber-back stopper for a secure fit. Complete the look in a sleek bodycon dress.
Fit & Features
- Metal filigree design
- Rubber-back stopper
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1264
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Fun Cuffed Denim Mini Skirt
Forever classic with a fun touch, this denim mini skirt boasts a flattering bodycon fit and a unique cuffed hem. Pair with a cute top for a farmer's market!
Fit & Features
- Denim fabric
- High-rise waist, belt loops
- Front button and hidden zipper closure
- Dual front and back pockets
- Mini-length cuffed hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06601-000002
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple And Chic Ponte Knit Mini Skort
Simple and chic, this ponte knit mini skort will elevate your casual looks. It features a mid-rise waist, a mini-length overlay with a double slit design, and hidden shorts for coverage.
Fit & Features
- Ponte knit fabric, moderate stretch
- Mid-rise waist
- Mini-length overlay
- Double slit side design
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000066
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: BLACK, OFF, WHITE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Spring Vibes Daisy Studded Jelly Tote Bag
This adorable jelly tote bag is the perfect accessory for your fab spring festivities! Made with a trendy jelly material, this tote features a small rectangular design with adorable daisy-studded accents. Includes two top handle straps and a removable long chain-link shoulder strap. Style with a flowy skater dress and heels for weekend brunch!
Fit & Features
- Jelly material
- Small rectangular design
- Small daisy-studded accents
- Dual top handle straps
- Foldover with snap-button closure
- Removable chain-link shoulder strap, lobster clasps
Style Number/Barcode: 07203-1983
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Time For Vacay High Rise Tropical Palazzo Pants
These tropical palazzo pants are ready for your next vacay! Features a high-rise waist and wide-leg silhouette for a flattering fit. The palm print on knit fabric adds a touch of paradise to any outfit. Complete the look with the matching top.
Shop Matching Top: Time For Vacay Tie Front Tropical Crop Top
Fit & Features
- Palm print, stretchy knit fabric
- High rise waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2482
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Bound Cutout Tropical Mesh Midi Dress
You'll be ready for your trip with this tropical mesh midi dress! This dress features a square neckline, spaghetti straps, and a bodycon fit for a flattering silhouette. The side cutout drawstring adds a touch of fun while the side slit and midi-length offer a sultry feel. Complete the look in trendy sandals.
Fit & Features
- Tropical palm leaf print
- Mesh fabric, stretchy knit lining
- Spaghetti straps
- Square neckline
- Side cutout drawstring
- Bodycon fit, side slit
- Runs true to size
Style Number/Barcode: 05102-5710
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chasing Sunshine Crochet Wedges
These crochet wedge mules serve beachy vibes with an elevated twist, perfect for brunch, shower celebrations, or dinners al fresco.
Fit & Features
- Square toe
- Wide strap
- Wedge sole
- Crochet material
- Runs true to size
Style Number/Barcode: 07406-000028
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Muse Watercolor Tie-Front Crop Top
Showcase your iconic style like the chic muse you are in this printed tie-front crop top! Crafted from a breezy woven fabric, it is detailed with a gorgeous watercolor print for a mesmerizing look. The top features a sleeveless V-neckline with a tie-front design at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a fitted cropped hem. Style with the matching midi skirt and espadrille wedges for a sunset dinner!
Shop Matching Bottoms: Chic Muse Watercolor Wrap-Slit Midi Skirt
Fit & Features
- Watercolor print
- Woven fabric
- V-neckline, tie-front
- Adjustable spaghetti straps
- Stretchy smocked back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2518
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Fling Heart-Shaped Sunglasses
Flirt up a storm in these adorable heart-shaped sunglasses perfect for the summer season! Featuring the cutest heart-shaped design with tinted lenses, these shades have a sleek thin metal frame with thin arms, a thin metal nose bridge, and rubber nose pads for support. Style with hoop earrings for a music festival!
Fit & Features
- Heart-shaped design
- Tinted lenses
- Thin metal frame and arms
- Thin metal nose bridge
- Rubber nose pads
- 100% UV protection
Style Number/Barcode: 07008-1048
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Gaze Chain Trim Cat Eye Sunglasses
Slip on these cat eye sunglasses knowing you're the cutest babe around! The chain trim arms add a touch of edge while the tinted lenses help protect your eyes from the sun.
Fit & Features
- Chain trim arms
- Cat eye shaped frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1134
Category Name: Vacation Looks
Price: $2.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool Girl Chic Strapless Abstract Mesh Mini Dress
Keep your going-out look cool girl chic with this sultry strapless abstract mesh mini dress. The airy sheer mesh fabric showcases a trendy abstract print and includes a full-length soft knit lining for coverage. The strapless straight-across neckline features an elastic band for a stretchy and secure fit, while the bodycon silhouette will flaunt your stunning curves. Style this short dress with a layered necklace and lace-up heels for drinks with the girls!
Fit & Features
- Stretchy sheer mesh fabric with soft knit lining
- Abstract print
- Strapless straight elasticized neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5558
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Reputation Halter Cutout Ribbed Knit Midi Dress
It's easy to keep up with your stylish reputation with this ribbed knit midi dress! Perfect for vacation or weekend plans, this midi dress boasts a trendy halter neckline with tie straps, sultry side, and back cutouts that flaunt some skin, and a bodycon silhouette adorned with a front slit. Complete the look with sunglasses and a cute purse!
Fit & Features
- Ribbed knit fabric, moderate stretch
- Halter neckline with tie straps
- Cutout side and back
- Front slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2000
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale