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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Prep For Paradise Strapless Tropical Jumpsuit
Prep yourself for paradise starting with this tropical jumpsuit to pack in your luggage! Made from a smooth knit fabric showcasing a palm tropical print, this jumpsuit features a strapless neckline with side-ruched seams that accentuate, a flattering wide-leg silhouette. Complete the look with sunglasses and sandals!
Fit & Features
- Smooth knit fabric, tropical palm print, moderate stretch
- Strapless neckline
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2520
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Booked And Unbothered Leopard Oversized Sunglasses
These oversized sunglasses bring instant glam with a bold frame that was made for poolside posing and low-key paparazzi moments.
Fit & Features
- Oversized leopard frames with metal trim
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000009
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Vibes High Slit Striped Knit Maxi Dress
This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.
Fit & Features
- Striped ribbed knit fabric, short knit lining, moderate stretch
- Scoop neckline
- Spaghetti straps
- High side slits
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5778
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovely Look Cold Shoulder Bodycon Lace Mini Dress
Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.
Fit & Features
- Lace fabric lined with stretchy knit
- Cold shoulder V-neckline
- Flutter short sleeve cuffs, spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3423
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flow My Way Chiffon Lace Trim Skater Dress
Effortlessly flow into any occasion in this simply chic chiffon skater dress - the perfect style for bridal showers, graduates, and birthday girls! The dress features a cold shoulder V-neckline with a delicate scalloped lace trim, adjustable spaghetti straps, short-sleeve cuffs, and a flattering fit-and-flare short-length silhouette. The airy chiffon fabric includes a stretchy knit lining. Complete the look with a sleek choker and earrings.
Fit & Features
- Cold shoulder design, V-neckline, scalloped lace trim
- Adjustable spaghetti straps, short-sleeve cuffs
- Back zipper and hook-eye closure
- Fit-and-flare skater silhouette
- Short-length hem
- Airy chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2053
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Favorite Strapless Cutout Floral Maxi Dress
Create a stunning aurora in this floral maxi dress for summer cocktail hours! The strapless neckline and side cutout provide a flattering silhouette, while the form-hugging fit accentuates your curves, and the high side slit offers a show of leg. Complete the look in strappy stiletto heels.
Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Strapless neckline
- Side cutout
- Form-hugging fit
- High side slit
- Runs true to size
Style Number/Barcode: 05101-3278
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Yacht Babe Floral Swim Cover Up
Soak up the sun looking like a babe in this swim cover-up! Wrap yourself in the beauty of summer with this long cover-up with a gorgeous floral print and a maxi form-hugging silhouette.
Fit & Features
- Floral print, sheer mesh stretchy fabric
- Low-rise waist, side cutouts
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 07105-000014
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Glam Rhinestone Butterfly Spiral Strap Sandals
Create a perfectly glam vibe with these rhinestone butterfly strappy sandals! Designed with sleek faux leather, they feature an almond-shaped toe, a dual toe strap and trendy spiral strap design, mini rhinestone embellishments for that glitzy shine, and organza butterfly accents with rhinestone detailing. They include a flat sole with a padded insole for comfortable wear. Style with a summer party dress!
Fit & Features
- Faux leather upper
- Almond toe
- Dual toe strap and spiral strap design
- Mini rhinestones
- Sheer organza butterfly accents with rhinestones
- Flat sole, padded insole
- Runs true to size
Style Number/Barcode: 07406-0362
Category Name: Vacation Looks
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catching Looks Crochet Palazzo Pants
Serving body and beach energy all in one slay. These crochet palazzo pants feature a high-rise waist and sheer wide-leg silhouette, perf for sipping cocktails, catching sunsets, or just catching looks.
Shop Matching Top: Catching Looks Crochet Bandeau Tube Top
Fit & Features
- Sheer crochet fabric with panty lining
- High-rise waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-000008
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sun-Kissed Moments Triangle Bikini Top
You'll have sun-kissed moments in this trendy triangle bikini top featuring the cutest seashell charm at the center of the bust. Style with the matching bikini bottoms.
Shop Matching Bottoms: Sun-Kissed Moments Tie-Strap Bikini Bottoms
Fit & Features
- Nylon-blend fabric, high stretch
- Triangle-shaped cups
- Seashell metal charm
- Adjustable spaghetti straps
- Tie-back spaghetti straps, beaded details
- Runs true to size
Style Number/Barcode: 07104-000006
Category Name: Vacation Looks
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Muse Floral Maxi Dress
Beach date or rooftop night out? You’re covered. With a drapey neckline and bold floral print, this maxi gives you that effortless she’s glowing moment.
Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Cowl halter neckline
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000273
Category Name: Vacation Looks
Price: $7.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Adorable Puff Sleeve Cutout Crop Top
Simply adorable, this puff sleeve cutout crop top will effortlessly elevate your casual 'fits. The smooth knit fabric offers a lightweight feel and plenty of stretch. The top features a ruched V-neckline, short puff sleeves with elasticized hems, and a bold front cutout below the bust. The open lower back is accented with an adorable tie-back design. Style this fitted top with high-rise jeans and strappy mules.
Fit & Features
- Stretchy knit fabric, double-lined front
- Ruched V-neckline
- Short puff sleeves
- Front cutout
- Open lower back, tie-back design
- Cropped, fitted
- Runs true to size
Style Number/Barcode: 06001-5329
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stackable Style Seven Pack Ring Set
The perfect seven-pack ring set to achieve stackable style! This set features an assortment of various designs and styles with glitzy rhinestone embellishments that bring some sparkle to your look. Complete the look with a chic handbag for any occasion!
Fit & Features
- Seven-pack ring set
- Rhinestone embellishments
- Various designs and styles
Style Number/Barcode: 07004-0399
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crusin' The Tropics Lace-Up Tropical Mini Dress
Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.
Fit & Features
- Tropical palm print, stretchy knit fabric, sewn-in lining
- Spaghetti straps
- V-neckline
- Lace-up back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5549
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Whimsical Essence Ruffled Floral Maxi Skirt
Adorn your look with the whimsical beauty of this ruffled floral maxi skirt in a sleek high-rise waist and a flowy silhouette made for sashaying through flower fields!
Fit & Features
- Woven fabric, floral print
- High-rise waist
- High front ruffled slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-0210
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Outside The Lines Tie Back Slit Marble Maxi Dress
Color outside the lines and rock this chic marble print maxi dress for dressy showers or summer events! With a square neckline and spaghetti straps, this dress flatters your figure with a form-hugging fit. The tie-back design adds a touch of unique style while the front slit showcases your legs along the maxi-length hem. Complete the look with earrings and heels.
Fit & Features
- Marble print, smooth knit fabric with stretchy lining
- Spaghetti straps
- Square neckline
- Tie back design
- Form-hugging fit
- Front slit
- Runs true to size
Style Number/Barcode: 05101-3455
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Constant Sensation V-Neck Corset Satin Skater Dress
Always be a constant sensation when you step out in this satin skater dress at parties or soirees! With a flirty V-neckline, comfortable shoulder straps, and a flattering corset-seam bodice, this dress has a playful skater silhouette and a short-length hem. The abstract print adds a touch of fun to the satin fabric. Complete the look with bracelets and a clutch!
Fit & Features
- Abstract print, satin fabric, woven lining, no stretch
- V-neckline, shoulder straps
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3291
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine On My Mind Strapless Tropical Skater Dress
This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.
Fit & Features
- Tropical palm print, gauze woven fabric, bust lining
- Strapless neckline
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5744
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Silhouette Rosette Ruffled Knit Mini Dress
The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.
Fit & Features
- Ribbed knit fabric with knit lining, plenty of stretch
- Scoop neckline with rosette detail
- Spaghetti straps
- Tiered ruffled mini-length hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5846
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Turn Heads Fringe Hoop Earrings
Giving major movement every time you turn your head. These fringe hoop earrings bring flirty vibes and just the right amount of drama to your outfit lineup.
Fit & Features
- Metal material
- Large thin hoop design
- Textured fringe disc detailing
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000042
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Admiring Looks PVC Platform Mules
From casual outings to formal soirees, these platform mules are sure to receive admiring looks! Designed with clear PVC straps that offer a modern, barely-there look, these block heel mules add a chic edge to every look.
Fit & Features
- 3.5" Block heel
- Square toe
- Clear PVC straps
- Luxe fit cushioned insole
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000007
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Afternoons Corset A-Line Midi Dress
Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.
Fit & Features
- Woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- Sweetheart neckline
- Corset bodice, built-in padded underwire bust
- Back zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3309
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Undeniable Halter V-Neck Crop Top
All you need is your undeniable sass and this crop top for an adorable style! It features a sultry halter V-neckline and a fitted pointed crop hem that flatters your figure on mineral wash stretchy rib knit fabric. Complete the look in jeans and sandals.
Fit & Features
- Mineral wash stretchy rib knit fabric
- Halter V-neckline
- Pointed crop hem
- Runs true to size
Style Number/Barcode: 06002-1880
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress
Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.
Fit & Features
- Eyelet fabric lined with stretchy knit
- Sweetheart neckline
- Adjustable bust drawstring, cutout
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5430
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale