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.

Breezy Weekend Vibes Floral Dress
Create an effortless weekend-ready look with this breezy floral printed midi dress. It features a sweetheart neckline, a ruched bust with a tie-front, short puff sleeves, a high waist seam, and a midi-length, A-line silhouette with a chic side slit. Style this dress with cute shades and strappy sandals.

Fit & Features
- Sweetheart neckline, ruched bust, tie-front
- Short puff sleeves, cinched hems
- High waist seam, back zipper, hook and eye closure
- Midi-length, A-line silhouette, side slit
- Small floral print
- Woven fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1598

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Story Chiffon Corset Top
Brighten up your closet with this fresh floral chiffon top for spring! It features long peasant sleeves, a ruffled off-the-shoulder neckline, and front hook-eye closures that lead to a cropped hem. Complete the look in high-rise jeans and sandals.

Fit & Features
- Long peasant sleeves
- Ruffled off-the-shoulder neckline
- Front hook-eye closures
- Cropped hem
- Floral chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1644

Category Name: Vacation Looks

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Fun Tie-Back Skater Romper
This flirty skater romper is all fun for your next dressy event! It features a sleeveless, square neck, spaghetti straps, a form-fitting design, and an open back with tie closure on the layered ruffle hem. Complete the look in sleek hoop earrings.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back with tie closure
- Layered ruffle hem
- Skater silhouette
- Form-fitting design
- Fits true to size
Style Number/Barcode: 06403-0202

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Out Of Town Long Sleeve Romper
Flying out of town? This long sleeve romper is sure to bring boho vibes to your vacay! It features long peasant sleeves, a plunge v-neckline, tie-back closure, an o-ring insert, and a cutout bodice that leads to flowy shorts. Complete the look in a chic panama hat.

Fit & Features
- Long peasant sleeves
- Plunge v-neckline
- Tie-back closure
- O-ring insert, cutout bodice
- Flowy shorts
- Gauze woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06303-0204

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cozy Day Cable Knit Skirt
Make your day a cozy one with a maxi skirt that is part chic, part comfy! The skirt features a cable knit pattern, an elastic high rise waist, a high side slit, and a maxi length hem. The skirt is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching crop top.

Shop Matching Crop Top: Cozy Day Cable Knit Crop Top

Fit & Features
- Elastic high-rise waist
- High side slit
- Maxi length hem
- Cable knit pattern
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0612

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cozy Day Cable Knit Crop Top
Make your day a cozy one with a crop top that is part chic, part comfy. The top features a sleeveless mock neck with frilly trim, a cable knit pattern, and a cropped hem. The top is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching maxi skirt.

Shop Matching Maxi Skirt: Cozy Day Cable Knit Skirt

Fit & Features
- Sleeveless mock neck
- Frilly trim
- Cable knit pattern
- Cropped hem
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4036

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless And Flowy Skater Dress
Create an effortless and flowy vibe in this breezy lace skater dress. It features a wrap-front V-neck and back design, short loose bell sleeves, a cinched and smocked high waist, and a short skater skirt with a fit and flare silhouette. The sheer lace fabric features a partial woven lining. Style this dress with strappy sandals.

Fit & Features
- Wrap-front V-neck and back
- Tie-back strap detail
- Short bell sleeves
- Cinched and smocked high waist
- Short skater skirt, fit and flare silhouette, front button-down design
- Sheer lace fabric, partial woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1475

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Greek Goddess Coin Swim Wrap
Create a goddess-worthy vibe in this mesh swim wrap featuring coin charms and a customizable self-tie closure. Complete the look in a sultry bikini set.

Fit & Features
- Sheer mesh
- Coin charms
- Customizable self-tie closure
- Soft and comfortable
Style Number/Barcode: 07305-0384

Category Name: Vacation Looks

Price: $7.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Outside The Lines Floral Print Crop Top
Style outside the lines and go for a bold chic look in this floral print crop top. Style with the matching skirt for a complete look.

Shop Matching Skirt: Outside The Lines Floral Print Maxi Skirt

Fit & Features
- Bold floral print, lined stretchy knit fabric
- Strapless
- Ultra crop-length hem
- Runs true to size
Style Number/Barcode: 06001-5658

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Getaway Vibes Caged Block Heel
Perf for your next getaway or every day, these heels are a must! The heels feature a closed-back, an adjustable ankle strap, a caged strap design, a peep-toe, a contrasting wood platform, and a block heel. Complete look with a tropical matching set and sunglasses.

Fit & Features
- Closed-back
- Adjustable ankle strap
- Faux leather caged strap design
- Peep toe
- Wood platform and block heel
- Runs true to size
Style Number/Barcode: 07401-3785

Category Name: Vacation Looks

Price: $12.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Reese High Rise Denim Shorts By Windsor Denim
Fall for the Reese high-rise denim shorts by Windsor Denim! She features a super high-rise waist, distressed accents, and a frayed cut-off hem on vintage medium wash denim with a color fade effect. Complete the look in a crop top and sandals.

Fit & Features
- Super high-rise waist
- Distressed accents
- Frayed cut-off hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Vintage medium wash denim, no stretch, color fading
- Runs true to size
Style Number/Barcode: 06603-0258

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Socialite Linen Babydoll Dress
The perfect linen babydoll dress for all of your social occasions is here! Featuring a sleeveless square neckline, adjustable spaghetti straps, a fitted bust, and a flared skater silhouette on a short-length hem. Complete the look in cute sandals and a straw bag.

Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Fitted bust, stretchy smocked back
- Flared skater silhouette
- Short-length hem
- Linen woven fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1536

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flaunt It Rhine Fringe Swim Wrap
Flaunt your glam while on vacay! Luxe up your swimwear in this rhinestone fringe wrap featuring a sheer mesh fabric with a customizable self-tie closure. Finish the look in sparkly slides.

Fit & Features
- Rhinestone fringe
- Sheer mesh fabric
- Customizable self-tie closure
Style Number/Barcode: 07305-0395

Category Name: Vacation Looks

Price: $5.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sparkle All Day Rhinestone Sandals
Sparkle all day in these rhinestone strap sandals featuring an almond toe, buckle closure, and a faux leather footbed. Complete the look in a cute sundress for a wine tasting.

Fit & Features
- Almond toe
- Rhinestone straps
- Ankle buckle closure
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07404-0996

Category Name: Vacation Looks

Price: $12.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Turn Up Halter Keyhole Mini Dress
Turn up the sultriness in this bodycon mini dress designed in a sleeveless, halter neck with tie-closure and a front hoop inset atop a keyhole cutout. Complete the look in dangly earrings for a mimosa brunch.

Fit & Features
- Sleeveless, halter with tie-closure
- Front hoop inset and keyhole cutout
- Bodycon silhouette
- Mini-length hem
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4570

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beach Stroll Linen Shorts
Take a stroll along the coast in these chic high waist linen shorts. They feature a fitted paper bag waist, a tie-front belt, front pockets, and a loose fit at the hem. Style with a basic bodysuit and strappy sandals.

Fit & Features
- High-rise fitted paper bag waist
- Tie-front belt
- Hidden front zipper, hook and bar, and button closures
- Front pockets
- Loose fit at the hem
- Lightweight linen-blend fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0188

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Take Me To Capri Square Neck Romper
Take this crepe romper on your trip to Capri! It features a sleeveless square neckline, spaghetti straps, a form-fitting bodice, and a flowy hem. Complete the look in dainty butterfly earrings.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Form-fitting bodice
- Flowy hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0980

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Desert Rose Tie Back Romper
Stand out from the crowd looking so gorg in this sleeveless romper featuring a square neckline, spaghetti straps, pleat details, and an open back with tie closure. Complete the look in PVC strap mules.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Pleat detail
- Flowy hem
- Open back with tie closure
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06503-0986

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Vacay Vibes Mesh Swim Wrap
Showcase major vacay vibes as you chill poolside in this airy mesh swim wrap! It features a high waist fit with a side tie design and a flowy floor-length silhouette. Style over your fave bikini and complete the look with oversized shades.

Fit & Features
- High waist fit
- Side tie design
- Flowy floor-length silhouette
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 07305-0412

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spring Picnic Lace-Up Espadrille Wedges
The perfect espadrille wedges for having the cutest picnic fit! They feature an almond toe, platform sole, and faux leather lace-up straps. Complete the look in a flirty skater dress.

Fit & Features
- Almond toe
- Platform espadrille sole
- Wedge style
- Faux leather lace-up straps
- Runs true to size
Style Number/Barcode: 07406-0298

Category Name: Vacation Looks

Price: $12.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Things Lace-Up Espadrille Wedges
Embrace all things spring! Sunnier days are ahead and these chic wedges are every girl's staple for creating fresh looks. They feature an almond toe, espadrille platform sole, and faux leather lace-up straps. Complete the look in a flowy sundress.

Fit & Features
- Almond toe
- Espadrille platform sole
- Wedge style
- Faux leather lace-up straps
- Runs true to size
Style Number/Barcode: 07406-0299

Category Name: Vacation Looks

Price: $12.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Tropic Strappy Back Midi Dress
Flaunt your figure on vacay girl! This floral tropic midi dress is perfect for a dinner with a view. Featuring a sleeveless V-neckline, spaghetti straps, a strappy open-back, a bodycon silhouette, and an asymmetrical hem. Complete the look in chic wedges.

Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Strappy open-back, tie closure
- Bodycon silhouette
- Asymmetrical midi-length hem
- Floral tropic print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4376

Category Name: Vacation Looks

Price: $19.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Laced in Daydreams Satin Halter Floral Mini Dress
This floral satin halter mini dress is sweet, flirty, and made for RSVP-ing yes, complete with dreamy lace details and a flattering A-line silhouette.

Fit & Features
- Floral print, woven satin fabric, bust lining
- Lace trim halter neckline, spaghetti strap tie
- A-line silhouette
- Lace trim front slit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000652

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cool Vibes Border Print Flare Pants
Effortlessly cool vibes all around! Style these flare pants for the perf desert festival fit. They feature a high-rise elasticized waist, form-fitting silhouette, and a flared hem on paisley border print knit fabric. Complete the look in a basic crop cami.

Fit & Features
- High-rise elasticized waistband
- Form-fitting silhouette
- Flared hem
- Paisley border print
- Stretch knit fabric
- Fits true to size
Style Number/Barcode: 06502-0871

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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