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.

Functional Style Denim Cargo Joggers
Functional fashion in a stylish utility design, these denim cargo joggers secure your must-haves while keeping your look edgy and cute! They feature a high-rise waist with a detachable good vibes keychain, a six-pocket styling, a jogger leg silhouette, and elasticized cuffs. Style with combat booties for a casual hang!

Fit & Features
- High-rise waist, detachable "Good Vibes" keychain
- Front button and hidden zipper closure
- Six-pocket styling, belt loops
- Jogger leg silhouette
- Elasticized cuffs
- Non-stretch denim fabric
- Runs true to size
Style Number/Barcode: 06302-0709

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Simple Life Crew Tank Midi Dress
All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.

Fit & Features
- Sleeveless crew neckline
- Wide tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4772

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fall Florals Mesh Crop Bustier
This fall calls for this sweet floral mesh bustier you'll adore styling with your fave denim! It features an off-the-shoulder neckline with short sleeve cuffs, a ruched bust with padded cups, and a hidden front hook and eye closures leading to the cropped hem. Complete the look in new jeans for a pumpkin patch!

Fit & Features
- Off-the-shoulder neckline
- Ruched bust, padded cups
- Short sleeve cuffs
- Hidden front hook and eye closures
- Cropped hem
- Floral mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4412

Category Name: Vacation Looks

Price: $7.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortless Everyday Ribbed Knit Midi Dress
Effortlessly chic for every day, this ribbed knit midi dress is a must-have for fall. It features a V-neckline, a combination of front spaghetti straps and long fitted sleeves, and a midi-length, curve-hugging silhouette. Style with ankle booties for coffee dates this season.

Fit & Features
- V-neckline
- Front spaghetti straps, long fitted sleeves
- Midi-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4975

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Autumn Chill Faux Wool Vest
Layer on this faux wool vest for a fashionably-chic look this autumn season. It features a sleeveless bodice, a lapel collar, an open front, hidden side pockets, and a relaxed fit. Style over a basic bodysuit and dress pants paired with ankle booties.

Fit & Features
- Sleeveless bodice
- Lapel collar
- Open front
- Hidden side pockets
- Relaxed silhouette
- Faux wool fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0334

Category Name: Vacation Looks

Price: $18.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Shimmer Slouch Stiletto Boots
Shimmer and shine with every step in these slouch stiletto boots featuring a pointy toe, all-over rhinestone embellishments, under-the-knee length, and a side zipper closure on faux suede material. Complete the look in a sassy mini dress.

Fit & Features
- Slouched design
- Pointy toe
- Stiletto heel
- Rhinestone embellishments
- Under-the-knee length
- Side zipper closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0847

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek And Stylish Moves Belted Pants
Step out and stun in these sleek and stylish pants! They feature a high-rise belted waist, front pockets, a skinny-leg silhouette, and a chic snake-embossed pattern. Pair with the matching crop top and clear heels.

Shop Matching Top: Sleek And Stylish Moves Crop Top

Fit & Features
- High-rise belted waist
- Hidden front zipper and button closure
- Front pockets
- Skinny-leg fitted silhouette
- Snake-embossed pattern
- Faux leather fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-0442

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sleek And Stylish Moves Crop Top
Step out and stun in this sleek and stylish crop top! It features a sleeveless square neckline, thin tank shoulder straps, a cropped, form-hugging fit, and a chic snake-embossed pattern. Pair with the matching belted pants and clear heels.

Shop Matching Bottoms: Sleek And Stylish Moves Belted Pants

Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Back zipper, hook and eye closure
- Cropped hem, form-hugging fit
- Snake-embossed pattern
- Faux leather fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06003-1715

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
New Rules High Rise Boyfriend Jeans
Set the style scene for the new season in these high-rise boyfriend jeans you're sure to be wearing on rotation! They feature a trendy asymmetrical waist and a boyfriend-leg design on vintage-inspired medium-wash denim with color fading. Complete the look in a corset top and mules.

Fit & Features
- High-rise asymmetrical waist
- Boyfriend leg design
- Front buttons and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim, color fading
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0398

Category Name: Vacation Looks

Price: $20.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Under The Sun Straw Buckle Slide Sandals
A pair of straw buckle strap sandals you'll reach for every sun shining day!

Fit & Features
- Round toe
- Dual straw buckle straps
- Comfortable footbed
- Traction bottom
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1290

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Side Ties Turtleneck Sweater Top
Your new favorite sweater top for wearing on those brisk autumn days! The sleeveless tank top features a turtleneck, cutout sides with tie closures, and a cropped hem on rib-knit fabric. Complete the look in flare pants and heels.

Fit & Features
- Sleeveless
- Turtleneck
- Cutout sides with tie closures
- Cropped hem
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1121

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Set A Trend Crepe Slit Midi Skirt
Set a trend by walking in wearing this crepe midi skirt for your weekend plans! It features a sleek high-rise waist, form-hugging fit and a sultry side slit perfect for styling with chic stiletto heels.

Fit & Features
- High-rise waist
- Form-hugging fit
- Side slit
- Midi-length
- Crepe fabric
- Fits true to size
Style Number/Barcode: 06501-0725

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Taylor High Rise Skinny Crop Jeans By Windsor Denim
Achieve an hourglass appearance in the Taylor High Rise Jeans by Windsor Denim! Put your curves on display in her flattering high-rise waist, skinny-leg design with a raw hem and light distressed accents. The jeans are composed of a Lycra-cotton blend denim fabric with stretch and shape retention. Complete the look in a chic top and heels.

Fit & Features
- High-rise waist
- Light distressed accents
- Skinny-leg design, raw crop hem
- Front button and hidden zipper closure
- 5-pocket styling, belt loops
- Lycra-cotton blend denim, minimal stretch
- Fits true to size
Style Number/Barcode: 06602-0338

Category Name: Vacation Looks

Price: $18.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chain My Mind Side Slit Midi Dress
This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.

Fit & Features
- Sleeveless square neck
- Chain link adjustable spaghetti straps
- Bodycon silhouette
- Side slit
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4800

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Catch My Glam Rhine Layer Necklace
Add this glam necklace to elevate your outfit! It features a four-layered design, one snake chain, one rhinestone chain, and one chain link with clear stone charms and a lobster clasp closure. Complete the look in a sleek midi dress for wine night.

Fit & Features
- Four-layered design
- One snake chain
- One rhinestone chain
- One chain link with clear stone charms
- Lobster clasp closure
Style Number/Barcode: 07002-1280

Category Name: Vacation Looks

Price: $2.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling Fierce Leopard Midi Skirt
Your wardrobe can't be tamed with the addition of this leopard midi skirt ready for a night on the prowl! Show your wild side in this high-rise skirt featuring a back zipper closure, a curve-hugging silhouette, and a high-cut front slit, composed of crepe chiffon-lined woven fabric. Complete the look in a twist crop top and strappy heels.

Fit & Features
- High-rise waist
- Back zipper closure
- Curve-hugging silhouette
- High-cut front slit, midi-length hem
- Leopard print
- Crepe chiffon fabric, lined, no stretch
- Fits true to size
Style Number/Barcode: 06401-0467

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Take A Trip Sweater Halter Dress
Taking a trip somewhere fab? You're gonna need this sweater halter dress perfect for looking chic on the go! It features a sleeveless bodice, cross straps with neck-tie closure, a bodycon silhouette, and a mini-length hem. Complete the look in linear earrings.

Shop More Styles: The Sweater Collection

Fit & Features
- Sleeveless halter neck
- Cross straps, neck-tie closure
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1605

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Head Over Heels Cutout Jumpsuit
Watch everyone fall head over heels for you in this cutout jumpsuit perfect for your next wine night! It features a sleeveless halter neckline, a cutout bust and waist accent, a partial open-back, and a flared hem. Complete the look in earrings.

Fit & Features
- Sleeveless halter neckline
- Cutout bust and waist accent
- Partial open-back
- Flared hem
- Knit fabric
- Fits true to size
Style Number/Barcode: 06502-1446

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major It-Girl Satin Midi Skirt
Bring the it-girl energy to your everyday look with this on-trend midi skirt. It features a high-rise waist, a V-wired front accent with ruched detailing, straps to lace up around the waist, a midi-length hem, a curve-hugging silhouette, and a high side slit. Style with a crop top and mules.

Fit & Features
- High-rise waist, V-wired front accent, ruching
- Thin straps to lace up around the waist
- Midi-length hem, fitted bodycon silhouette
- High side slit
- Smooth satin-knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06401-0492

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Minimalistic Sultry Midi Dress
Chanel a sultry minimalistic wardrobe for fall in this staple crepe midi dress featuring a sleek sleeveless V-neckline, bungee spaghetti straps, a curve-hugging silhouette, and a front slit accent. Complete the look in low-heeled mules and a chic hat.

Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Curve-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4782

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Your Favorite Crop Denim Shacket
Effortlessly laid back and cool, your favorite crop denim shacket to layer over your cutest daily fits! It features long sleeves with button cuffs and trendy distressed accents, a collar neckline, snap button-down closures, flap pockets, and a relaxed, curved hemline. Complete the look in a cute casual dress.

Fit & Features
- Collar neckline
- Long sleeves, button cuffs, distressed accents
- Snap button-down closures
- Flap pockets
- Relaxed fit, curve crop hemline
- Light wash non-stretch denim
- Runs true to size
Style Number/Barcode: 06203-0475

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Trio Three Pack Anklets
The perfect trio of anklets to adorn your semi-formal wear! This three-pack set features one snake chain anklet, one rhinestone charm anklet, and a multi-chain link anklet each with a lobster clasp closure. Complete the look in stiletto heels.

Fit & Features
- Three-pack anklet set
- One snake chain anklet
- One rhinestone charm anklet
- One multi-chain link anklet
- Each has a lobster clasp closure
Style Number/Barcode: 07003-0326

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
One Sided Cutout Back Bodysuit
Charm the crowd in this one-shoulder bodysuit featuring a long sleeve, form-fitting bodice, and a sultry cutout back. Complete the look in boyfriend jeans for dinner with friends.

Fit & Features
- One-shoulder neckline
- Long sleeve
- Form-fitting bodice
- Cutout back design
- Thong bottom, snap button closures
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06001-4410

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Bow Charm Cat Eye Sunglasses
The dainty bow detail on these sunglasses adds a soft-girl twist to this fierce cat eye shape—perfect for brunch 'fits, content days, or any moment you wanna look cute and unbothered.

Fit & Features
- Sleek cat eye frames
- Bow charm
- TInted lenses
- 100% UV protection
Style Number/Barcode: 07008-000057

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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