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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STYLE SPOTLIGHT

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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.

Vacay Views Floral Midi Dress
Soak in those stunning vacay views in this chic floral midi dress! It features a sleeveless bodice, a wrap-front V-neckline, spaghetti straps, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some skin. The smooth and stretchy knit fabric features an all-over tropical floral print. Complete the look with strappy heels.

Fit & Features
- Sleeveless bodice, wrap-front V-neckline
- Spaghetti straps
- Fitted midi-length silhouette, asymmetrical hem
- Form-hugging fit
- Tropical floral print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4441

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Soul Swirls Mesh Cover Up
Unveil your retro soul in this swirl print cover-up featuring long sleeves, a v-neckline, bodycon fit, and a center front drawstring so you can customize the fit. Complete the look in a string bikini set and sunglasses.

Fit & Features
- Long sleeves
- V-neckline
- Bodycon fit
- Center front adjustable drawstring
- Bodycon fit, mini-length hem
- Sheer stretchy mesh swirl print fabric
- Fits true to size
Style Number/Barcode: 06001-4307

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Perfect For Paradise Midi Dress
This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length asymmetrical hem
- Form-fitting silhouette
- Tropical floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4474

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Alluring One-Piece Swimsuit
So alluring, this one-piece swimsuit will give you that sexy poolside look. It features a one-shoulder neckline with a thin tank strap, a padded bust, daring sheer mesh inserts in a wrap design to create a chic silhouette, and a semi-cheeky fit. Style this swimsuit with a flowy duster.

Fit & Features
- One-shoulder neckline, thin tank shoulder strap
- Removable padding
- Sheer mesh inserts in a wrap design
- Semi-cheeky fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0284

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glam Tassels Rhinestone Belt
Glam and glitzy, create the perfect shine with this tassel belt featuring rhinestone drops, a layered design, and a lobster clasp closure. Complete the look in a glitter bikini set for a pool party.

Fit & Features
- Rhinestone drop tassels
- Layered design
- Lobster clasp closure
Style Number/Barcode: 07301-0431

Category Name: Vacation Looks

Price: $6.97 $23.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Casual Glam Espadrille Sandals
Bring the casual glam to your summer looks with these embellished sandals. They feature an open round toe, dual rhinestone adorned straps, an espadrille trim, and a flat sole with contrast stitching. Style with a flowy midi dress and a layered necklace.

Fit & Features
- Open round toe
- Dual rhinestone embellished straps
- Espadrille trim
- Flat sole, contrast stitching
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1069

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Making Waves Linen Tie Front Top
All eyes on you strolling the beach in this linen tube top on vacay! It features a strapless, sleeveless, square neck with a flirty tie-front and a smocked back panel on a cropped hem. Complete the look in the matching bottoms.

Shop Matching Bottoms: Making Waves Linen High Rise Shorts

Fit & Features
- Strapless, sleeveless, square neck
- Tie-front detail
- Smocked back panel
- Cropped hem
- Linen woven fabric, double-lined, no stretch
- Runs true to size
Style Number/Barcode: 06003-1558

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Gorgeous Floral Romper
Showcase an effortlessly gorgeous look in this breezy floral printed romper! It features a sleeveless V-neckline, adjustable spaghetti straps, a sheer crochet waist design, and flowy shorts. The semi-sheer chiffon fabric includes a knit lining. Style this romper with chic mules.

Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Back zipper, hook and eye closure
- Sheer crochet waist design
- Flowy shorts
- All-over floral print
- Semi-sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0207

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Slip Into Something Floral Mesh Maxi Dress
The dress you “accidentally” wear to steal the spotlight. This floral mesh maxi drapes you in a soft cowl neckline with a low back and curve-hugging fit that’s ready for cocktails at sunset!

Fit & Features
- Floral print, mesh fabric, soft and stretchy knit lining
- Cowl halter neckline with tie straps
- Low cut back
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000341

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Glam Gauze Knit Mini Dress
Keep it glam and carefree with a mini dress that gives off that effortless vibe! The dress features a sleeveless V-neckline with crochet trim, adjustable spaghetti straps that cross at the back, an unlined crochet lace waist, an open back with ties, and a mini length silhouette with tiered ruffles. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules.

Fit & Features
- Sleeveless V-neckline, crochet trim
- Adjustable spaghetti straps, cross-back
- Unlined crochet lace waist
- Open back with ties
- Tiered ruffles, mini-length silhouette
- Lined gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1098

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Breeze Halter Bodysuit
Breezy and blissful. awaken paradise in this halter bodysuit featuring a sleeveless bodice, tie closure, and an o-ring inset atop a form-fitting silhouette, dual snap-button closure, and a thong bottom. Complete your island vacay look in a midi skirt.

Fit & Features
- Sleeveless, halter, tie closure
- O-ring inset
- Form-fitting
- Dual snap-button closure, thong bottom
- Tropical print, knit-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4133

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Life's Sweet Puff Sleeve Tie Top
Life is so much sweeter with this cute puff sleeve top! It features a sweetheart neckline with a cinched bust, cropped hem, and an open back with tie closure. Complete the look in a flirty mini skirt for a day out with the girls.

Fit & Features
- Short puff sleeves, elastic cinched hems
- Sweetheart neckline
- Cinched bust
- Cropped hem
- Open-back, tie closure
- Lined woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1835

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
The Essential Basic Tube Top
This essential basic tube top is the perfect base to create an insta-worthy outfit of the day! This top features a strapless, sleeveless, square neckline and a fitted crop hem on cotton-lined fabric. Complete the look in trendy best-selling bottoms and heels.

Fit & Features
- Strapless, sleeveless
- Square neckline
- Cropped hem
- Lined cotton fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1264

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Vibes Bandeau Bikini Top
This bikini top is a total vibe for summer! Enjoy the sunshine in this sleek swim top featuring a convertible strap design so you can style it multiple ways and removable padding for support and shaping. Complete the look in the matching bikini bottoms and sunglasses.

Shop Matching Bikini Bottoms: Summer Vibes Cheeky Bikini Bottoms

Fit & Features
- Convertible tie design
- Removable padding for support and shaping
- Runs true to size
Style Number/Barcode: 07104-0695

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pretty Clear PVC Cork Wedges
It's pretty clear these wedges belong in your closet! They feature an almond toe, a wide PVC strap, and a cork platform sole. Complete the look in a cute matching set for a vacation.

Fit & Features
- Almond toe
- Wide PVC strap
- Cork platform sole
- Runs true to size
Style Number/Barcode: 07406-0317

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Daze Halter Sweater Dress
Bring the summer vibes with this bright and trendy halter sweater dress. It features a sleeveless scoop neckline, halter spaghetti straps, an open back with a tie-back design, and a midi-length, curve-hugging silhouette. The lightweight sweater knit fabric showcases an all-over multi-hued chevron pattern. Complete the look with espadrille sandals.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless scoop neckline
- Halter spaghetti straps, tie at the back of the neck
- Open back, tie-back strap design
- Midi-length, form-fitting silhouette, scalloped hem
- Multi-hued chevron pattern
- Unlined sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1312

Category Name: Vacation Looks

Price: $12.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
She's Ready For Brunch Crop Top
The answer is always yes to brunch! Have the cutest look of your squad in this adorable ditsy floral printed top. It features a sleeveless subtle sweetheart neckline, adjustable spaghetti straps, ruched detailing at the bust, and a cropped fit with a tie-back design. Complete the outfit with the matching mini skirt and your fave mules.

Shop Matching Bottoms: She's Ready For Brunch Mini Skirt

Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Ruching at the bust
- Back zipper closure
- Cropped, form-hugging fit, tie-back design
- Ditsy floral print, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1754

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Jetset Getaway Tropical Midi Dress
Wanna get away? Jetset off to paradise with this tropical floral dress in your lineup! It features a sleeveless scoop neck, spaghetti straps, a cross-back strap design with a tie closure, a form-fitting silhouette, a side ruched seam, and an asymmetrical midi hem with a side slit. Complete the look in lace-up heels.

Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Open-back, cross-back strap design, tie closure
- Form-fitting silhouette
- Side ruched seam
- Asymmetrical midi-length hem, side slit
- Tropical floral print, stretchy knit-lined fabric
- Runs true to size
Style Number/Barcode: 05102-4373

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunset Cruise Floral Midi Dress
You'll be ready for a sunset cruise on the water in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, side ruched detailing, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some leg. The dress features an all-over tropical floral print. Complete the look with strappy sandals.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back strap design
- Side ruching
- Midi-length, form-fitting silhouette, asymmetrical hem
- Tropical floral print
- Stretchy knit fabric, partial lining at the bust
- Runs true to size
Style Number/Barcode: 05102-4375

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunday Strolls Floral Tie Front Top
Take a stylish stroll to brunch in this floral tie-front top featuring adorable short puff sleeves, a plunge V-neckline, and a cropped hem. Complete the look in a denim mini skirt.

Fit & Features
- Short puff sleeves, elasticized hems
- Plunge V-neckline
- Tie-front detail
- Cropped hem
- Floral print
- Lightweight woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1322

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Last Night Of Vacay Lace-Up Top
Go out with a sizzle in this tropical crop top on your vacay! It features a sleeveless, mock neck, and a sexy front cutout with lace-up closure. Complete the look in the matching skirt.

Shop Matching Skirt: Last Night Of Vacay Lace-Up Skirt

Fit & Features
- Sleeveless, mock neck
- Front cutout with lace-up closure
- Cropped hem
- Tropical print lined-knit fabric
- Runs true to size
Style Number/Barcode: 06001-3990

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Last Night Of Vacay Lace-Up Skirt
Go out with a sizzle in this tropical mini skirt on your vacay! It features a high-rise waist, bodycon silhouette, and a side cutout with lace-up detail. Complete the look in the matching top.

Shop Matching Top: Last Night Of Vacay Lace-Up Top

Fit & Features
- High-rise waist
- Side cutout with lace-up
- Bodycon silhouette
- Mini-length hem
- Tropical print lined-knit fabric
- Runs true to size
Style Number/Barcode: 06501-0590

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Here Comes The Sun Strapless Ruffled Mini Dress
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The short tube dress features ruched sides and a ruffled hem, adding a playful touch to the bodycon silhouette.

Fit & Features
- Double-lined brushed knit fabric, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Bodycon silhouette
- Mini-length tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000242

Category Name: Vacation Looks

Price: $32.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Rhine Drops Layered Lariat Choker
It's raining rhine! Add a glam touch to your formal wear with this layered lariat choker featuring a three-row design, rhinestone drops, and dainty chain links with a lobster clasp closure. Complete the look in sleek heels.

Fit & Features
- Layered three-row design
- Rhinestone drops
- Dainty chainlinks
- Lobster clasp closure
Style Number/Barcode: 07002-1144

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials