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.

Good Times Marble Halter Dress
Let the good times flow in this marble print mini dress perfect for vacation and sipping mojitos! It features a sleeveless, halter neckline with a ruched drawstring and tie closure, a cutout bodice, and a form-hugging fit on the knit-lined fabric. Complete your fab look with lucite mules.

Fit & Features
- Halter neckline, ruched drawstring, tie closure
- Cutout bodice
- Form-hugging fit
- Mini-length hem
- Marble print knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4531

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Resort Ready Palm Print Mini Dress
You'll be ready for your getaway at the resort with this tropical mini dress in your arsenal! It features a sleeveless square neck, sleek spaghetti straps, a palm print, and a curve-hugging silhouette. Complete your vacay look in espadrille wedges.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Palm print
- Soft brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4681

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sangria Please Striped Wide Leg Pants
Can't you imagine wearing this striped halter top while sipping on a sangria? Set the tone for vacay-ready in these striped pants featuring a high-rise waist, paper bag style, and a wide-leg silhouette. Complete the look in the matching top.

Shop The Matching Top: Sangria Please Striped Halter Top

Fit & Features
- High-rise elasticied waist
- Paperbag style
- Wide leg silhouette
- Striped pattern
- Gauze woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0613

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Slash Of Style Cutout Crop Top
Stand out from the crowd in this elevated basic crop top featuring cap sleeves, a crew neck, and trendy cutout accents, and a fitted hem. Complete the look in distressed jeans for a casual fit.

Fit & Features
- Cap sleeves
- Crew neck
- Cutout accents
- Fitted crop hem
- Brushed knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4378

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Set Sail Tie-Front Crop Top
Get ready to set sail on a sunset cruise in this breezy crop top. It features half-length kimono-style sleeves, a V-neckline, a tie-front design, and a cropped, relaxed fit. Style this top with high-rise shorts.

Fit & Features
- Half-length kimono-style sleeves
- V-neckline
- Tie-front
- Cropped, relaxed fit
- Woven gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1187

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Social Lite Linen Envelope Skort
A social lite such as yourself needs this trendy linen skort for looking fab on the go! It features a high-rise waist with a front side button closure and an envelope-style overlay on texture linen-blend fabric. Complete the look in a boho floral top and heels.

Fit & Features
- High-rise waist, back elastic band
- Front side button closure
- Envelope-style overlay
- Shorts lining
- Texture linen-blend fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0193

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Press Pause Paper Bag Woven Shorts
Press pause and admire how stylish you'll be in these woven shorts featuring a trendy, paper bag high-rise waist, tie-front belt, pleat detailing, a four-button up closure, side pockets, and a form-fitting silhouette. Complete the look in a basic tank top and espadrille wedges.

Fit & Features
- Paper bag high-rise waist
- Tie-front belt
- Pleat detailing
- Four button-up closure, side pockets
- Form-fitting silhouette
- Woven Tencel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0192

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Perfectly Distressed Oversized Denim Jacket
This trendy denim jacket is perfectly distressed for that cute and casual vibe! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, destructed details, and an oversized fit. Layer this jacket over a mini dress and complete the look with your fave mules.

Fit & Features
- Collared neckline
- Long sleeves, single-button details
- Button-down front
- Buttoned chest pockets, side pockets at the waist
- Distressed detailing
- Light wash denim fabric, no stretch
- Oversized fit
Style Number/Barcode: 06203-0453

Category Name: Vacation Looks

Price: $17.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Out Of Office Gradient Oversized Sunglasses
These sunnies say “catch me on a yacht”—even if it’s just brunch. With oversized gradient lenses and glam hardware, these sunglasses are made for low-effort luxe and spontaneous selfies.

Fit & Features
- Rimless square-shaped oversized design
- Metal chain-link detail on the arms
- Flexible nose pads
- Gradient-tinted lenses
Style Number/Barcode: 07008-000058

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: PINK

Available Size: NS
I've Got Needs Scoop Neck Crop Top
This cute, versatile crop top is ready to fulfill all of your outfit needs! It features a sleeveless, scoop neck, tank straps, crafted from stretchy rib-knit lined fabric. Complete the look in denim shorts and sneakers.

Fit & Features
- Sleeveless, scoop neck
- Tank straps
- Cropped hem
- Rib-knit lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1235

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Carefree Vibes Chic Satin Kimono
Showcase carefree vibes this summer season in this chic satin kimono. It features half-length kimono-style sleeves, an open front, a flowy, relaxed fit, side slit accents, and fringe detailing at the hem. Style over a basic bodysuit and cutoff denim shorts.

Fit & Features
- Half-length kimono-style sleeves
- Open front
- Flowy, relaxed fit
- Side slits
- Fringe detailing at the hem
- Smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1397

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep It Chic And Sleek Sunglasses
Keep your summer look chic and sleek with these on-trend shades! The sunglasses feature hexagon-shaped lenses with a gold metal trim, thin arms, and tinted lenses. Style with hoop earrings.

Fit & Features
- Hexagon-shaped lenses
- Gold metal trim
- Thin arms
- Nose pads
- Tinted lenses
Style Number/Barcode: 07008-0958

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Abstract Art Satin Wide Leg Pants
Abstract art you can wear! Slay an art gallery opening in these fierce satin pants featuring a high-rise elasticized waistband, front pleating, and a wide-leg silhouette. Complete the look in the matching top.

Shop Matching Top: Abstract Art Satin Convertible Top

Fit & Features
- High-rise elasticized waistband
- Front pleating
- Wide-leg silhouette
- Abstract print, satin fabric
- Runs true to size
Style Number/Barcode: 06402-0414

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Simply Elevated One-Shoulder Bodysuit
This simply elevated sleeveless bodysuit will bring the chic vibes to your casual look. It features a one-shoulder neckline with a single tank shoulder strap, a side cutout at the waist with an adjustable drawstring, a thong bottom, and a form-hugging fit. Style with high-rise jeans.

Fit & Features
- Sleeveless one-shoulder neckline
- Tank shoulder strap
- Side cutout at the waist, adjustable drawstring
- Thong bottom, dual snap button closure
- Form-hugging fit
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4400

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Under The Palms Halter Skater Dress
Get ready to relax under the palms in this adorable printed skater dress. It features a sleeveless V-neckline with halter straps, side cutouts leading to a strappy banded back design, a smocked high waist, and a flowy skater skirt silhouette. The lightweight gauze fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie at the back of the neck
- Side cutouts, strappy banded back design, tie closure
- Smocked high waist, flowy skater skirt
- Tropical palm leaf print
- Gauze fabric, knit skirt lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4499

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paradise Cove Slit Maxi Skirt
Enter paradise cove in true vacay style! This tropical maxi skirt features a high-rise waist, front high-cut slit, and a trendy palm print on stretchy lined fabric. Complete the look in the matching top and sunglasses.

Shop Matching Top: Paradise Cove Cowl Neck Crop Top

Fit & Features
- High rise waist
- Front high-cut slit
- Maxi-length hem
- Tropical palm-print
- Stretchy lined knit fabric
- Runs true to size
Style Number/Barcode: 06501-0659

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Paradise Cove Cowl Neck Crop Top
Enter paradise cove in true vacay style! This tropical tank top features a sleeveless, cowl neck, sleek bungee spaghetti straps, cropped hem, and a trendy palm print on stretchy lined fabric. Complete the look in the matching bottoms and sunglasses.

Shop Matching Bottoms: Paradise Cove Slit Maxi Skirt

Fit & Features
- Sleeveless, cowl neck, bungee spaghetti straps
- Cropped hem
- Tropical palm-print
- Stretchy lined knit fabric
- Runs true to size
Style Number/Barcode: 06001-4262

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Elise Destructed Denim Mini Skirt by Windsor Denim
The Elise destructed denim skirt will elevate all of your casual 'fits. The cute mini skirt by Windsor Denim features a high-rise waist, subtle distressing, a short, form-hugging fit, and a trendy frayed hem. The dark wash denim fabric offers a moderate stretch. Style with a crop top and mules.

Fit & Features
- High-rise waist
- Subtle distressing
- Five-pocket and belt loop design, front button, hidden zipper closure
- Mini-length, form-hugging fit
- Frayed hem
- Dark wash denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0059

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sultry Spice Cutout Maxi Dress
Sultry and spicy! Make jaws drop in this sleeveless maxi dress featuring a one-shoulder neckline, waist cutout details and a form-fitting silhouette with a high-cut side slit for a show of skin. Composed of stretchy slinky knit fabric. Finish the look in lucite mules.

Fit & Features
- Sleeveless, one-shoulder neckline
- Waist cutout details
- Form-fitting silhouette
- High-cut side slit
- Maxi-length hem
- Slinky knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4528

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Take Me On A Getaway Midi Dress
Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.

Fit & Features
- Sleeveless halter neckline, thin straps that tie at the back of the neck
- Front ruching, adjustable drawstring
- Front waist cutout
- Midi-length, form-fitting silhouette, side slit
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1414

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Beachy Vibes Maxi Sweater Dress
Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back, cross-back strap design
- Fitted, maxi-length silhouette, side slit
- Sweater knit fabric, crochet detailing, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1421

Category Name: Vacation Looks

Price: $17.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Passport To Paradise Midi Dress
The island may be breathtaking but you'll also be a sultry view in this sleeveless midi dress featuring a square neck, spaghetti straps, a cutout bodice, asymmetrical hem, and a side ruched drawstring that lets you customize the fit. Complete the look in a straw floppy hat.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Cutout bodice
- Side ruched drawstring
- Form-fitting
- Asymmetrical midi hem
- Slinky knit lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4620

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Babe Sleeveless Bodycon Slit Mini Dress
A sleeveless knit mini dress boasts a flattering square neckline, a bodycon fit, and a flirty front slit. Perfect for layering or styling alone.

Fit & Features
- Knit fabric, moderate stretch
- Square neckline
- Shoulder straps
- Front slit
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 06005-2002

Category Name: Vacation Looks

Price: $32.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Leafy Greens Ruffle Skater Romper
Wear your greens! Steal the show on vacay in this palm leaf print romper featuring a sleeveless, square neck, spaghetti straps, open back with tie closure, and a ruffled skater-style skirt with shorts lining. Complete the look in strappy heels.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open back with tie closure
- Ruffled skater-style skirt
- Shorts lining
- Palm leaf print
- Brushed knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-0992

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks

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Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials