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.

Just Like Magic Chrome Sandals
Add sparkle and glow to everyday or dressy look in these chrome sandals featuring a square toe, rhinestone embellished strap, and a slide-on/off styling. Perfect for styling with a classic little black dress.

Fit & Features
- Square toe
- Rhinestone embellished band
- Slide-on/off styling
- Chrome footbed
- Runs true to size
Style Number/Barcode: 07404-1008

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Staple Oversized Sunglasses
Block the rays with these trendy staple sunglasses featuring an oversized, metal square frame, gradient colored lens, rubber nose supports, and a sleek design. Complete your outfit with a cute crossbody bag.

Fit & Features
- Oversized metal square frame
- Gradient colored lens
- Rubber nose supports
- Sleek design
- 100% UV protection
Style Number/Barcode: 07008-0945

Category Name: Vacation Looks

Price: $3.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Mix It Up Twist Cutout Bodysuit
Mix up your closet in vibrant color! This sleeveless bodysuit features spaghetti straps, a color block design, and a V-neck with a twisted bust atop a sultry cutout bodice. Complete the look in denim shorts and strappy mules.

Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Twisted bust, cutout bodice
- Thong bottom, dual snap button closure
- Color block design
- Form-fitting
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4305

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunkissed Florals Twist Crop Top
Let the sunshine on this flirty floral crop top perf for a brunch with the girls! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, twist accent bodice, and a back smocked panel with zipper closure. Complete the look in the matching bottoms.

Shop Matching Bottoms: Sunkissed Florals A-Line Skirt

Fit & Features
- Sleeveless, sweetheart neck, adjustable spaghetti straps
- Twist accent bodice
- Cropped hem
- Back smocked panel, zipper closure
- Floral print, lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1824

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Go With The Flow Halter Jumpsuit
You love an effortless, carefree look, so this lightweight jumpsuit is perfect for your weekend plans. It features a sleeveless halter neckline, a center keyhole cutout, a backless design, a high waist seam, a form-hugging fit, and flared pant legs. Style with a layered charm necklace.

Fit & Features
- Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
- Center keyhole cutout
- Open back
- High waist seam
- Form-hugging fit, flared pant legs
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-1023

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On Edge High Rise Fray Denim Shorts
Keep your style on edge in these high-rise denim shorts! They feature a flattering high-rise waist, distressed accents, and a frayed cutoff hem on vintage-inspired dark wash denim with a color fade effect. Complete the look in a graphic top and sandals.

Fit & Features
- High-rise waist
- Distressed accents
- Frayed cutoff hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Dark wash denim, color fade effect, no stretch
- Fits true to size
Style Number/Barcode: 06603-0236

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Destination Vacay Tropical Floral Mini Dress
Jet set to your destination vacay in this tropical floral print mini dress, perfect for sunset happy hour. Designed with a square neck, adjustable spaghetti straps, and a short fitted silhouette, style with gold hoops and slide-on sandals.

Fit & Features
- Scuba knit fabric, stretchy knit lining
- Tropical floral print
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper closure
- Mini-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-6077

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Illusion Mesh Straw Hat
Bring the drama with a hat that is anything but basic! The hat features an illusion mesh body and a wide brim. Complete your look with a midi dress and sunnies that will have you brunch ready!

Fit & Features
- Illusion mesh body
- Wide brim
Style Number/Barcode: 07302-0583

Category Name: Vacation Looks

Price: $7.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Fab Oversized Sunglasses
Style up your summer looks with these trendy fab oversized shades! The sunglasses feature a plastic square-shaped frame with thin arms and tinted lenses. Complete your outfits with a mini shoulder bag.

Fit & Features
- Oversized plastic square-shaped frame
- Thin arms
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0930

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Zoey Sleeveless Chiffon Party Dress
Special Occasion

You'll look oh-so-darling in the Zoey chiffon party dress! She features a sleeveless square neckline, adjustable spaghetti straps, an open back with a lace-up strappy design, a fitted high waistband, and a short party skirt with a flared-out silhouette. The lined chiffon fabric features an all-over floral burnout pattern for a pretty look. Perfect for a semi-formal wedding, complete your guest outfit with chic heels.

Fit & Features
- Sleeveless square neckline
- Adhesive bra recommended
- Adjustable spaghetti straps
- Open back, lace-up strappy design, tie closure
- High waistband, short party skirt, fit and flare silhouette
- Lined chiffon fabric, floral burnout pattern
- Runs true to size
Style Number/Barcode: 05001-1002

Category Name: Vacation Looks

Price: $19.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Retreat Mesh Mini Dress
Look like you're ready to jet-set off to an island retreat in this mesh mini dress! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, curve-hugging fit. The lined mesh fabric features an all-over tropical palm leaf print. Complete your look with espadrille wedges.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching down the side seams
- Mini-length, form-fitting silhouette
- Tropical palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4534

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Summer Style Floral Romper
Showcase a sweet summer style in this flirtatious floral romper. It features a strapless square neckline, a stretchy smocked bodice, a high waist with a tie-front belt, flowy shorts, and an all-over dainty floral print pattern. Complete the look with espadrille sandals.

Fit & Features
- Strapless square neckline
- Stretchy smocked bodice
- High waist, tie-front belt
- Flowy mid-thigh length shorts
- Floral print
- Lightweight woven fabric
- Runs true to size
Style Number/Barcode: 06403-0179

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feeling Butterflies Huggies Set
Swoon for this whimsical huggie earrings set! It features a variety of six sets each with dainty rhinestone designs with a post-back closure. Complete the look in a charming linen sundress for an outdoor party.

Fit & Features
- Six-pack variety set
- Dainty rhinestone designs
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1280

Category Name: Vacation Looks

Price: $4.00 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunkissed Florals A-Line Skirt
Let the sunshine on this flirty floral skirt perf for brunch with the girls! It features an elasticized high-rise waist, a tiered flowy a-line silhouette, and a short-length hem. Complete the look in the matching top.

Shop Matching Top: Sunkissed Florals Twist Crop Top

Fit & Features
- High-rise elasticized waist
- Tiered flowy a-line silhouette
- Short-length hem
- Floral print, lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0124

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ready Set Vacay Gauze Maxi Dress
Pack this flowy lightweight maxi dress in your carry-on as you jet set off on vacay! It features a sleeveless V-neckline, halter spaghetti straps, a smocked high waist with chic cutouts leading to an open strappy back, and a floor-length maxi silhouette with a side slit and a relaxed fit. Style with espadrille sandals.

Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie at the back of the neck
- Smocked high waist, cutouts leading to open back
- Strappy back design
- Maxi-length silhouette, side slit
- Woven gauze fabric, mini skirt knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4497

Category Name: Vacation Looks

Price: $22.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Palisades Paisley High Rise Pants
Look pretty in these paisley pants for a retro vibe! It features a high-rise elasticized waistband, pleat detailing, and wide-leg silhouette crepe woven fabric. Complete the look in the matching top.

Shop Matching Top: Palisades Paisley Tie-Front Top

Fit & Features
- High-rise elasticized waistband
- Pleat detailing
- Wide-leg silhouette
- Paisley print
- Crepe woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-0461

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Blushing Tropics Button-Up Top
Make all the cheeks blush when you step out in this tropic chiffon top! Featuring long sleeves with button cuffs, a collared neckline, a button-down front, and a flowy silhouette. Complete the look in the matching top.

Shop Matching Top: Blushing Tropics Bandeau Top

Fit & Features
- Long sleeves, button cuffs
- Collared neckline
- Button-down front
- Flowy silhouette
- Floral tropic print
- Chiffon fabric
- Runs true to size
Style Number/Barcode: 06003-1659

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Beauty Printed Midi Skirt
Bring that trendy bohemian style to your summer look with this lightweight woven midi skirt. It features a high-rise fitted waist, a side knot detail leading to a wrap-front design, a midi-length, flowy fit, and an all-over boho-inspired multi-print pattern. Complete the outfit with a neutral bodysuit.

Fit & Features
- High-rise waist, back zipper closure
- Side knot detail
- Wrap-front design, front slit
- Midi-length, flowy silhouette
- Multi-print pattern
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0131

Category Name: Vacation Looks

Price: $14.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunflower State Chiffon Corset Top
It's full bloom ahead! Create a sweet look in this chiffon floral corset top featuring adorable puff sleeves, a ruched sweetheart neck, hook-eye front closures, and a cropped hem. Complete the look in denim shorts.

Fit & Features
- Puff sleeves
- Ruched sweetheart neck
- Front hook-eye closures
- Cropped hem, back smocked panel
- Sunflower print
- Partially sheer texture chiffon fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1641

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropic Like It's Hot Halter Midi Dress
It's vacay season and this halter midi dress is here for it! Featuring a sleeveless, high neckline with a tie closure, cutout bodice with a cinch accent, and a bodycon midi-length hem. Composed of a nylon-blend knit fabric with a moderate stretch. Finish the look with trendy mules.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless, high halter neckline, tie closure
- Cutout bodice, cinch accent
- Bodycon silhouette
- Midi-length hem
- Nylon-blend knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1305

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Here To Play Halter Skater Romper
Perfect for day or night play, this cute romper combines comfort with head-turning appeal. This flirty, figure-flattering piece features a daring plunge neckline and playful skater silhouette that moves with you.

Fit & Features
- Smooth knit, stretchy fabric
- Plunge halter neckline, tie closure
- Flowy skater silhouette
- Short hem
- Runs true to size
Style Number/Barcode: 06503-000060

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Optical Illusion Checkered Crop Top
This crop top is no illusion, it's really that cute! Featuring cap sleeves, a crew neck, swirl checkered print, and a trendy open-back with tie closure. Complete the look in distressed denim shorts for a cool concert fit.

Fit & Features
- Cap sleeves
- Crew neck
- Swirl checkered print
- Cropped hem
- Open-back, tie closure
- Fits true to size
Style Number/Barcode: 06001-4281

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Vibe Ruched Bodysuit
You'll look like such a vibe in this trendy ruched bodysuit! It features a sleeveless one-shoulder neckline with a single spaghetti strap, a bold waist cutout, and a form-hugging fit. Style with faux leather pants and hoop earrings.

Fit & Features
- Sleeveless one-shoulder neckline, single spaghetti strap
- Waist cutout
- Ruched detailing
- Form-hugging fit
- Dual snap button closure, thong bottom
- Sleek knit lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4245

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Worth It Linen Tube Top
This linen tube top is worth taking on your next weekend adventure! It features a sleeveless, bodice, a convertible design so you can style it multiple ways, and a cropped hem. Complete the look in the matching bottoms.

Shop Matching Bottoms: Worth It Linen Wide Leg Pants

Fit & Features
- Sleeveless bodice
- Convertible design
- Multiple ways to style
- Cropped hem
- Linen fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06003-1601

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials