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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Western Charm Cactus Drop Earrings
Show off a cute western charm with these cactus drop earrings! They feature a textured circular post with a hanging cactus charm with an engraved boho-inspired design. Include a post-back closure. Style with a flowy summer dress and cowboy boots!
Fit & Features
- Textured circular post
- Hanging cactus charm, engraved boho-inspired design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1645
Category Name: Vacation Looks
Price: $3.96 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Remy High-Rise Acid-Wash Denim Shorts by Windsor Denim
Create a bold festival-inspired look with the Remy acid-wash denim shorts by Windsor Denim! They feature a high-rise waist, a frayed cut-off hem, and a form-hugging fit. The trendy acid-wash denim fabric offers a moderate stretch. Style with a crop top and cowboy boots!
Fit & Features
- High-rise waist
- Frayed cut-off hem
- Front button, hidden zipper closure
- Five-pocket and belt loop design
- Acid-wash denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0324
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Hour Tie-Front Linen Vest
Perfect for every day, you'll love the minimal vibes of this linen vest! The sleeveless lapel collar and tie-front closure add a modern aesthetic to any outfit, while the cropped hem finishes the chic look. Style with the matching pants.
Shop Matching Bottoms: Golden Hour High-Rise Cargo Wide-Leg Linen Pants
Fit & Features
- Linen blend fabric, no stretch
- Lapel collar neckline
- Tie-front closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1724
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish And Edgy Cropped Denim Jacket
Layer on this cool cropped denim jacket for a stylish and edgy look. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, distressed detailing, and a cropped, frayed hem. Pair this jean jacket over your fave casual romper and complete the look with booties.
Fit & Features
- Collared neckline
- Long sleeves, single-button details
- Complete button-down front
- Buttoned chest pockets
- Denim fabric, distressed detailing
- Cropped, frayed hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06203-0226
Category Name: Vacation Looks
Price: $16.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Treasure Linen Wide-Leg Pants
Everyone will be asking where you found these trendy linen wide-leg pants! You'll love the high-rise waist offering a flattering fit, while the wide-leg silhouette gives off that effortlessly chic vibe. The waist is accented with pleating, dual front pockets, and a back zipper closure for a secure fit. Complete the look with the matching corset top!
Shop Matching Top: Trendy Treasure Strapless Linen Corset Top
Fit & Features
- Linen-blend woven fabric, stretchy knit lining
- High waist
- Wide-leg silhouette
- Pleating, back zipper and hook-eye closure
- Dual front pockets
- Back zipper
- Runs true to size
Style Number/Barcode: 06302-0814
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Splashin' Around Eyelet Ruffle Swim Shorts
Splish-splash-looking flirty in these eyelet ruffle swim shorts perfect for pool parties, beach days, and vacations!
Fit & Features
- Eyelet fabric
- High-rise elasticized waist
- Ruffle trim
- Runs true to size
Style Number/Barcode: 07105-000001
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daytime Cheer Fit And Flare Ruffle Floral Dress
Spread daytime cheer in this fit and flare floral dress! Made from soft chiffon fabric, this dress is adorned with a ditsy floral print for a whimsical touch. This playful dress features a sweetheart neckline with ruffle trim, adjustable spaghetti straps, and a charming keyhole bust tie. The stretchy smocked waist and tiered ruffled hem create a flattering fit and flare silhouette. Complete the look with a cute purse and sandals!
Fit & Features
- Ditsy floral print, chiffon fabric, stretchy knit lining
- Ruffle trim sweetheart neckline
- Adjustable spaghetti straps
- Stretchy smocked waist
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05102-5447
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Style Icon Cutout Bodycon Midi Dress
This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Tank strap
- Asymmetric waist cutout
- Midi-length hem
- Bodycon silhouette
- Stretchy ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-5201
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Lovin' Crochet Knit Mini Dress
You'll love the summer vibes this crochet knit mini dress brings to your happy hour look. Designed with a strapless neckline and sultry side slit, the bodycon fit will flaunt your stunning curves.
Fit & Features
- Sheer crochet knit fabric with knit lining, moderate stretch
- Strapless straight-across neckline
- Ruched side seam, adjustable drawstring, side slit
- Mini-length asymmetric hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000046
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic And Elevated Trouser Shorts
Refresh your wardrobe with these chic and elevated trouser shorts! They feature a high-rise waist, a front button closure, front pleated detailing, and a fitted silhouette. The smooth crepe fabric includes a woven lining. Style with the matching blazer.
Shop Matching Ivory Blazer: Chic And Elevated Woven Blazer
Shop Matching Pink Blazer: Bold Moves Woven Blazer
Shop Matching Turquoise Blazer: Bold Moves Woven Blazer
Fit & Features
- High-rise waist
- Front button, hidden button and zipper closure
- Front pleating
- Front pockets
- Fitted
- Crepe fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06403-0263
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacay Mood Strapless Tropical Knit Jumpsuit
This eye-catching tropical knit jumpsuit will put you in the mood for a beachy vacay! Designed with a stretchy knit fabric with a multi-colored tropical print pattern, this jumpsuit will bring the bold allure to your dreamy getaway. It features a strapless straight-across neckline, a fitted high waist for a snatched look, and a relaxed wide-leg silhouette. Style with chunky gold hoops and strappy sandals.
Fit & Features
- Stretchy knit fabric, bust lining
- Tropical print
- Strapless straight neckline
- Fitted high waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2454
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Way She Moves Striped Bra Top
This striped bra top has entered the girl's vacay chat! Boasting a sexy plunge neckline and cutout back, you'll be the hit of the trip. Pair with the matching skirt to complete the look!
Shop Matching Bottoms: Way She Moves Striped Midi Skirt
Fit & Features
- Striped print, scalloped trim, stretchy knit fabric
- Plunge V-neckline
- Wide shoulder straps
- Cutout back with tie closure
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-2258
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Sweetheart Mesh Mini Dress
You'll be such a stunning sweetheart in this gorgeous mesh mini dress! Featuring a flattering ruffled padded sweetheart neckline with an off-the-shoulder design and a curve-hugging fit with all-over ruched detailing, this dress is perf for your next date night with bae. Pair with some clear lucite heels for that it-girl look.
Fit & Features
- Off-the-shoulder neckline, short sleeve cuffs
- Sweetheart neck, built-in padded bust
- Ruffle trim detailing, all-over ruching
- Back zipper and hook and eye closure
- Short, form-hugging fit
- Sheer mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1539
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coolest Look Aviator Metal Sunglasses
Make any outfit cool in these aviator sunglasses! They feature a sleek metal frame, smoke-tinted lense to help protect your eyes, and rubber nose supports and arms for comfort. Complete the look in trendy sandals.
Fit & Features
- Aviator sunglasses
- Sleek metal frames
- Smoke-tinted lense
- Rubber nose supports and arms
Style Number/Barcode: 07008-1101
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Spicy Scoop Neck Mini Dress
Sweet and spicy, this mini dress is exactly what your next club night needs! It features a sleeveless scoop neckline, dual spaghetti straps, a strappy back design, and side ruched seams to accentuate your curves along the short bodycon silhouette. Complete the look in eye-catching stiletto heels.
Fit & Features
- Sleeveless scoop neckline
- Dual spaghetti straps
- Strappy back design
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4804
Category Name: Vacation Looks
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Striped Shirt Skater Dress
Step out in this perfectly striped shirt dress to look cute for picnics in the park, family gatherings, or graduations! It features long sleeves with buttoned cuffs, a collar v-neckline, a corset-seam illusion waist, a cutout lace-up back design, and a short skater silhouette. Complete the look with teardrop earrings.
Fit & Features
- Long sleeves, buttoned cuffs
- Collar v-neckline
- Corset-seam illusion waist
- Cutout lace-up back design
- Skater silhouette, short-length hem
- Striped print, poplin non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 05102-5048
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Sight Strapless Ruffled Eyelet Mini Dress
You'll be the sweetest sight in this strapless eyelet mini dress as the lovely bride-to-be or birthday girl! The strapless neckline and flexible boning provide a comfortable and flattering fit, while the tiered ruffled mini-length hem adds a playful touch. Complete the look with earrings and strappy block heels.
Fit & Features
- Eyelet woven fabric, sewn-in knit lining
- Strapless neckline
- Back zipper and hook-eye closure
- Flexible boning inserts
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3042
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Girl Halter Open Back Tropical Mini Dress
Getaway to paradise in this tropical mini dress! Featuring a sultry cowl halter neckline and an open back with dual spaghetti strap ties, this dress will show plenty of skin on vacay while the bodycon silhouette and mini-length hem flatter your figure. Complete the look with doorknocker earrings and heels.
Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Halter cowl neckline
- Open back with dual spaghetti strap ties
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5795
Category Name: Vacation Looks
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flutter Away Layered Skater Dress
Flutter away in a twirl-worthy skater dress! The dress features a sleeveless wrap V-neckline, adjustable spaghetti straps, and a tiered skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with mules and dainty rings.
Fit & Features
- Sleeveless V-neckline, wrap-front design
- Adjustable spaghetti straps
- Back zipper, hook and eye closure
- Tiered skater skirt
- Chiffon fabric, knit lining, minimal stretch
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-1458
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just One Night Ruched Midi Dress
Make your night out a fab one with a dress that stuns! The dress features a sleeveless cowl neckline, spaghetti straps, curve-defining ruche detail, and a high-side slit for a display of leg along the midi-length hem. The dress is composed of a smooth knit fabric that offers a moderate stretch. Complete the look with mules.
Fit & Features
- Sleeveless cowl neckline, sticky bra recommended
- Spaghetti straps
- Ruching, high side slit
- Midi length hem
- Form-hugging fit
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1107
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce Summer Vibes Rhinestone Fishnet Mini Dress
Layer on this fab rhinestone fishnet mini dress over short dresses, bodysuits, or swimsuits to give off fierce summer vibes! It features a crew neckline, short sleeves, a mini-length hem, a form-hugging fit, and all-over sparkling iridescent rhinestone embellishments on the sheer unlined fishnet fabric. Complete the look with sleek hoop earrings.
Fit & Features
- Crew neckline
- Short sleeves
- Mini-length hem
- Form-hugging fit
- Mini iridescent rhinestone embellishments
- Sheer unlined fishnet fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4766
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Essential Ribbed Knit Midi Dress
This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Form-hugging fit
- Side slit, midi-length hem
- Double-lined rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4961
Category Name: Vacation Looks
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Babe Halter V-Neck Corset Crop Top
You'll be the cutest babe in this room in this sleeveless corset crop top! Featuring a flattering halter V-neckline, supportive underwire bust, and hidden front hook and eye fasteners, with figure-enhancing flexible boning while the cropped hem adds a touch of playfulness. Complete the look with the matching bottoms.
Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants
Fit & Features
- Woven fabric, sewn-in knit lining, no stretch
- Halter V-neckline
- Underwire bust
- Hidden front hook and eye fasteners
- Flexible boning
- Back zipper and hook-eye closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2542
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Vibe Ruched Knit Tube Top
Show off the cutest vibe in this trendy tube top with ruching down the sides for a flattering silhouette. Perf for styling with your fave pair of denim!
Fit & Features
- Cotton knit fabric, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000205
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: RED, WHITE, BLACK
Available Size: S, M, L