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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Flirty Focus Strapless Rib Knit Tube Crop Top
Attract all the attention when you're in this flirty tube crop top all summer long! Featuring a strapless neckline and a form-hugging fit, this top will accentuate your figure in all the right ways. The hanky-cropped hem adds a playful touch to the rib knit fabric. Complete the look in a denim skort.
Fit & Features
- Rib-knit stretchy fabric
- Strapless neckline
- Hanky cropped hem
- Runs true to size
Style Number/Barcode: 06002-1884
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pop The Cork Platform Heels
The perfect platform block heels for daytime celebrations! These shoes are designed to elevate your look with sleek faux leather straps and cork material for a unique style.
Fit & Features
- Block heel
- Almond toe
- Faux leather toe and adjustable ankle strap, buckle closure
- Platform sole
- Cork material
- Runs true to size
Style Number/Barcode: 07401-5283
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Follow The Sun Lace-Up Tropical Midi Dress
Follow the sun to your next destination in this tropical midi dress! This bodycon dress flatters your figure with a square neckline, spaghetti straps, and a lace-up back. The side ruched seam and slit add a touch of chic to the midi-length hem. Complete the look in sunglasses and sandals!
Fit & Features
- Tropical print, stretchy knit fabric, bust lining
- Square neckline
- Spaghetti straps
- Lace-up back
- Bodycon silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5745
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clueless Vibes Denim Belted Mini Skirt
Serving throwback prep with a spicy upgrade. This denim houndstooth mini skirt brings the drama with a statement belt and a mini silhouette made to steal glances.
Fit & Features
- Houndstooth pattern, denim cotton-blend fabric, no stretch
- Mid-rise belted waist
- Bodycon mini-length silhouette
- Front button and hidden zipper closure
- Back pockets, belt loop accents
- Runs true to size
Style Number/Barcode: 06601-000007
Category Name: Vacation Looks
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Bloom Strapless Floral Smocked Tube Top
Bare your shoulders in this cute strapless floral tube top this summer! Made from floral-printed eyelet fabric, this top adds a touch of charm to any outfit. The strapless neckline and fitted crop hem flatter your figure, while the stretchy smocked bodice ensures a comfortable fit. Complete the look in a trendy skirt for any occasion!
Fit & Features
- Floral printed eyelet fabric, stretchy knit lining
- Strapless neckline
- Stretchy smocked bodice
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5366
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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No You Hang Up Tube Mini Dress
Get ready to wow in this tube mini dress for your next date! This dress is designed with an alluring twist bust with a keyhole cutout that shows some skin, while the form-hugging A-line silhouette accentuates your curves.
Fit & Features
- Texture knit stretchy fabric
- Strapless tube sweetheart neckline
- Twist bust, keyhole cutout
- Form-hugging, A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000018
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Style Button Ruffled Striped Linen Skater Dress
Catch everyone's attention with your cute style in this striped skater dress perfect for casual summer plans! Made with striped linen fabric, this dress is perfect for any occasion. Featuring a scoop neckline with a bust tie and adjustable spaghetti straps, this dress is both stylish and comfortable. The button down front and ruffled trim add a fun touch, while the skater silhouette and short-length hem create a flattering look. Complete the look with hoop earrings and trendy sandals.
Fit & Features
- Striped print linen-blend fabric lined with woven, no stretch
- Scoop neckline with bust tie
- Adjustable spaghetti straps
- Button down front and ruffle trim
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5731
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Slay Halter Cowl Neck Ribbed Knit Maxi Dress
This sleek halter cowl neck maxi dress is a simple chic style that will make your casual outfits slay! Made with a lightweight stretchy ribbed knit fabric, it features a sleeveless draped cowl neckline with tie-back halter spaghetti straps, an alluring open back with a lower tie-back strap, and a form-hugging maxi-length silhouette to flaunt your stunning figure. Pair with slip-on sandals for a relaxing weekend getaway.
Fit & Features
- Stretchy ribbed knit fabric, partial front knit lining
- Cowl neckline, halter spaghetti straps
- Open back, tie-back strap
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5685
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Day Puff Sleeve Cut Out Denim Romper
Indulge in the dreamy vibes of this denim romper for casual bridal showers, birthdays, or graduation parties! The V-neckline and cutout sides add a touch of allure, while the form-hugging fit accentuates your curves. Made from soft denim fabric, the short-length hem offers a flirty and comfortable style. Complete the in wedge sandals.
Fit & Features
- Denim fabric, minimal stretch
- Back zipper and hook-eye closure
- Cutout sides
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0372
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romantic Effect Halter Tie Back Floral Satin Top
Indulge in the ultimate romantic effect in this halter tie-back floral satin top! Featuring a flattering V-neckline and delicate halter spaghetti straps, this top turns heads with its open tie-back closure. The fitted pointed hem and beautiful floral design on luxurious satin fabric make it a must-have for your wardrobe. Complete the look in high-rise jeans and mules.
Fit & Features
- Floral design, satin woven fabric
- Spaghetti straps
- Open tie-back closure
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2382
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemain Charm Halter Open Back Tie Dye Maxi Dress
Meet the bohemian charm of this tie dye maxi dress for summer soirees and parties! Featuring a halter cowl neckline and an alluring open back with tie closure, this dress exudes sensuality. The side ruched seams and form-hugging fit accentuate your curves, while the front slit and sheer maxi-length hem add a chic touch! Complete the look with earrings and a clutch.
Fit & Features
- Tie dye print, stretchy mesh fabric, sewn-in knit lining
- Halter cowl neckline
- Open back with tie closure
- Form-hugging fit
- Front slit
- Runs true to size
Style Number/Barcode: 05101-3445
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stripes of The Day Tie Side Romper
Show your stripes of the day on this trendy romper! It features a sleeveless, v-neck, adjustable spaghetti straps, surplice bodice, and an elasticized waist with side tie detail. Complete the look in chunky heels for the perf summer vibe.
Fit & Features
- Sleeveless, v-neck, adjustable spaghetti straps
- Surplice bodice
- Elasticized waist, side tie detail
- Striped print
- Woven lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06403-0182
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Total Appeal One-Shoulder Bodycon Mini Dress
This one-shoulder mini dress features a unique asymmetrical neckline and is made from super soft, stretchy knit material. The bodycon silhouette perfectly highlights your curves for date nights or parties.
Fit & Features
- Soft, stretchy knit material
- One-shoulder neckline
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3553
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get The Look Crochet High-Rise Pants
Curate effortless vibes in these crochet high-rise pants, perfect for pairing with the matching top for a cute look!
Fit & Features
- Embroidered crochet fabric, sewn-in panty knit lining
- High-rise waist, side zipper and hook-eye closure
- Sheer design
- Runs true to size
Shop The Matching Top: Get The Look Crochet Halter Crop Top
Style Number/Barcode: 06402-000005
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Babe In Stripes Strapless Cutout Ribbed Knit Midi Dress
Be a bold babe in this striped knit midi dress perfect for styling over your swimsuit or wearing alone. Featuring a strapless neckline and cutout bodice, this bodycon dress will hug your curves in all the right places. The stretchy ribbed knit fabric and midi-length hem add comfort and style, while the striped pattern adds a fun twist. Complete the look with sandals and sunnies!
Fit & Features
- Striped pattern
- Stretchy ribbed knit fabric
- Strapless neckline
- Cutout bodice
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1939
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Enchanting A-Line Floral Chiffon Midi Dress
Have everyone under your spell in this floral chiffon midi dress as a stunning wedding guest or to attend a garden party! Featuring a square neckline with a bust tie, elasticized shoulder straps, and an A-line silhouette, this dress flatters any figure. The front slit and midi-length hem add a touch of sophistication. Complete the look in block heels and earrings!
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Elasticized shoulder straps
- Square neckline, bust tie
- Back zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3304
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take A Bow Print Canvas Tote Bag
Carry your essentials in this sweet canvas tote bag. This charming tote features an eye-catching bow print design that adds a touch of feminine flair to any outfit and a spacious interior for your everyday essentials!
Fit & Features
- Top handles
- Bow print design
- Spacious interior
- Canvas material
Style Number/Barcode: 07203-000025
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stun The Scene V-Neck Lace Mesh Crop Top
Your attraction will be undeniable in this scenic print mesh crop top perfect for adding a romantic look! It features a flirty V-neckline adorned with delicate lace trim and ribbon, spaghetti straps, a babydoll silhouette that flatters, and a flowy cropped hem. Complete the look in a denim skirt and sandals for any casual plans!
Fit & Features
- Scenic print, sheer mesh fabric, moderate stretch
- Spaghetti straps
- V-neckline, lace trim and ribbon
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 06001-5391
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miami Nights Sleeveless Tropical Slit Maxi Dress
Turn up the heat in Miami in this tropical maxi dress on vacay! The square neckline and spaghetti straps accentuate your curves in a form-hugging fit while the high side slit adds a touch of sassy sophistication. Let the tropical print and maxi-length hem transport you to a paradise getaway! Complete the look in sandals.
Fit & Features
- Tropical print, knit fabric, stretchy short lining
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5624
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In My Element V-Neck Bow Ruffled Floral Romper
Time to show your playful side in this sleeveless ditsy floral romper for spring-to-summer fun! With a surplice V-neckline, adjustable spaghetti straps, and an open crisscross back, you'll turn heads. The front bow tie waist and ruffled short-length hem add a touch of fun to the ditsy floral print woven fabric. Complete the look in stiletto mules and earrings!
Fit & Features
- Ditsy floral print woven fabric, partial knit lining, minimal stretch
- Surplice V-neckline
- Adjustable spaghetti straps, open back, cross-back strap design
- Back zipper with hook and eye closure
- High waist seam, tie-front bow
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06403-0379
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachy Perfection Strappy Straw Block Heels
These straw heels are the definition of beachy perfection! They feature a square toe with dual straps, an adjustable ankle strap with buckle closure to secure the style, and a trendy circular block heel. Complete the look with a cute tote bag for a beach trip!
Fit & Features
- 2.5" Circular block heel
- Square toe
- Dual straps
- Adjustable ankle strap with buckle closure
- Straw material
- Faux leather padded insole
- Runs true to size
Style Number/Barcode: 07401-4863
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish In Stripes Strapless Wide Leg Knit Jumpsuit
Spend your days looking stylish in this striped jumpsuit perfect for layering over your swimsuit or wearing on its own. The jumpsuit features a strapless neckline and an adjustable drawstring waist that cinches, leading to the flattering wide-leg silhouette. Complete the look with chic sunglasses.
Fit & Features
- Striped pattern, knit fabric, moderate stretch
- Strapless neckline
- Adjustable drawstring waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2539
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oasis Babe Floral Wrap Tie Sarong
Perfect for poolside lounging or beachfront dining, this sarong adds instant babe status to your vacation wardrobe. This mesh sarong can be styled as a swimsuit cover-up or a stylish skirt with its adjustable tie design, with a vibrant floral print that captures tropical vibes.
Fit & Features
- Mesh fabric, floral print, stretchy
- Wrap tie adjustable waist
- Sheer design
Style Number/Barcode: 07105-000015
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In For The Frills Mid-Rise Eyelet Ruffle Shorts
Romp around in these adorable eyelet ruffle shorts for weekend brunch or a festival! Designed with a smocked mid-rise waist and flirty lace trim.
Fit & Features
- Eyelet lace chiffon fabric
- Stretchy knit shorts lining
- Smocked mid-rise waist
- Ruffled silhouette
- Runs true to size
Style Number/Barcode: 06403-1110
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free