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.

Sweet Intentions Floral Printed Duster
Show off your sweet side with a floral duster that is too stylish to resist! It features long fitted sleeves, a long, flowy length, and a sheer mesh fabric with an all-over blooming rose print. Layer this adorable duster over a basic bodysuit and your fave pair of denim.

Fit & Features
- Long fitted sleeves
- Long, flowy length
- Relaxed fit
- Sheer mesh fabric, moderate stretch
- Rose print
- Runs true to size
Style Number/Barcode: 06202-0255

Category Name: Vacation Looks

Price: $16.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
90's Babe Crop Tee
Throw it back to the 90's babe in this graphic crop tee! It features short sleeves, a crew neck, and a boxy silhouette with a raw hem. Complete the look in boyfriend jeans for chilling with friends.

Fit & Features
- Short sleeves, crew neck
- Graphic script reads, '90's Babe'
- Boxy silhouette, raw crop hem
- Cotton fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1061

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
One And Done Lattice Front Jumpsuit
A chic jumpsuit for everything on your social calendar! This sleeveless jumpsuit features adjustable spaghetti straps, a v-neckline with lattice, a fitted empire waist on a wide-leg silhouette. Complete the look in rhinestone hoops.

Fit & Features
- Adjustable spaghetti straps
- V-neckline, lattice front
- Fitted empire waist
- Wide-leg silhouette
- Back zipper closure
- Woven fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06402-0378

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ruched Hour Satin Bodycon Dress
Get ready for clubbing with the girls in this satin bodycon dress featuring a square neck, spaghetti straps, and a curve-defining side ruched seam along the mini-length hem. Complete the look in rhinestone heels and a clutch.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruched seam, bodycon silhouette
- Mini-length hem
- Satin-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4319

Category Name: Vacation Looks

Price: $6.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lights Out Halter Faux Wrap Dress
Create a lasting impression! This sultry halter dress is perfect for a night out with the girls. It features a plunging neckline, a faux wrap skirt, and ruched side seams to accentuate your curves on the short hem. Complete the look with a statement ring.

Fit & Features
- Plunge halter neckline, tie closure
- Faux wrap skirt
- Ruched side seams
- Bodycon fit, short hem
- Sleek knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4339

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Threads Cowl Neck Mini Dress
Flaunt your florals for all the compliments! This floral printed mini dress features a sleeveless cowl neck, sleek spaghetti straps, and a bodycon silhouette. Composed of a lined mesh fabric with a moderate stretch. Style with lace-up heels.

Fit & Features
- Sleeveless cowl neck
- Spaghetti straps
- Floral print pattern
- Bodycon mini-length silhouette
- Sheer mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1381

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweetheart Certified Halter Skater Dress
Look sweet as can be in this skater dress and turn heads at shower celebrations or parties. The flattering halter square neckline accentuates your shoulders while the playful skater silhouette creates a feminine flare that moves with you.

Fit & Features
- Poplin woven fabric, stretchy knit lining
- Square halter neckline, ponte knit bodice
- Back zipper hook-eye closure
- Skater silhouette, hidden side pockets
- Short length hem
- Runs true to size
Style Number/Barcode: 05101-000474

Category Name: Vacation Looks

Price: $46.90

Availability: In Stock

Available Color: BLACK

Available Size: S
Cross My Heart Rhinestone Choker Set
Add edgy-glam to your everyday style in this choker set featuring four delicate assorted chains with a rhinestone cross charm. Lobster clasp closure. Perfect for achieving a layered look with a low-cut blouse.

Fit & Features
- Four pack set
- Rhinestone cross charm
- Delicate assorted chain link styles
- Lobster clasp closure
Style Number/Barcode: 07002-1099

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Classic Crepe Fitted Skort
Classic and chic, this crepe skort is perfect to dress up or down. It features a high-rise waist, fitted shorts, and a front skirt overlay with a small slit. Style this skort with a pretty blouse and mules for an elevated look.

Fit & Features
- High-rise waist
- Back zipper closure
- Fitted shorts
- Front skirt overlay, mini-length, small slit
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0964

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Love The Look Lace-Up Mini Skirt
You'll fall in love with the chic look of this fitted mini skirt. It features a high-rise waist, a side lattice design with a sultry slit, and a short, curve-hugging fit. The smooth faux suede fabric offers a moderate stretch. Style this skirt with a bodysuit and mules.

Fit & Features
- High-rise waist
- Back zipper closure
- Side lattice design, tie detail
- Side slit
- Mini-length form-fitting silhouette
- Faux suede fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0391

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Lush Leopard Active Leggings
Slay your workout in this leopard-active legging for your next gym sesh! It features a flat, high-rise waistband, leopard print, skinny-leg design, and flatlock seams that provide comfortable wear. Composed of moisture wick fabric to keep you cool and dry. Style with the matching sports bra.

Shop The Matching Sports Bra: Lush Leopard Active Sports Bra

Fit & Features
- Flat high-rise waistband
- Leopard print
- Skinny-leg design
- Flatlock seams
- Moisture wick fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 07103-0769

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Serenade Me V-Neck Crop Top
A dreamy look awaits in this sleeveless top with a flattering V-neckline and fitted crop hem that flaunts your figure. Pair with the matching skirt to complete the look!

Fit & Features
- Double-lined smooth knit stretchy fabric
- V-neckline
- Wide shoulder straps
- Fitted crop hem
- Runs true to size
Shop The Matching Skirt: Serenade Me Bodycon Midi Skirt
Style Number/Barcode: 06001-000042

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lush Leopard Active Sports Bra
Slay your workout in this leopard active sports bra for your next gym sesh! It features a high neckline, removable padding for support and shaping, an elasticized hem, and a sleek racerback. Composed of moisture wick fabric to keep you cool and comfortable. Style with the matching leggings.

Shop The Matching Leggings: Lush Leopard Active Leggings

Fit & Features
- High neckline
- Removable padding
- Elasticized hem
- Racerback
- Leopard print
- Moisture wick fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 07107-0724

Category Name: Vacation Looks

Price: $7.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ready Or Not Scoop Neck Crop Top
Ready or not, this crop top will be your new fave essential! It features long fitted sleeves and a scoop neck on ribbed knit fabric with a moderate stretch. Complete the look in mom jeans and mules.

Fit & Features
- Long fitted sleeves
- Scoop neckline
- Cropped hem
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1256

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lily Girl Mesh Floral Ruched Skirt
Unveil this cute floral skirt for a wine night with the ladies! It features a high-rise waist, floral pattern, ruched side seams that accentuate your curves along the mini-length hem. Composed of mesh knit-lined fabric with a moderate stretch. Style with the matching top.

Shop The Matching Top: Lily Girl Mesh Floral Corset Top

Fit & Features
- High-rise waist
- Floral pattern
- Ruched side seams
- Mini hem
- Mesh-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0545

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Lily Girl Mesh Floral Corset Top
Unveil this cute floral crop top for a wine night with the ladies! It features long sleeves, a sweetheart neckline with hook-eye closures, and a cropped hem on mesh-lined fabric with a moderate stretch. Style with the matching skirt.

Shop The Matching Skirt: Lily Girl Mesh Floral Ruched Skirt

Fit & Features
- Long sleeves
- Sweetheart neckline
- Hook-eye front closures
- Cropped hem
- Mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-3784

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Country Roots Faux Wool Rhine Panama Hat
Dig up your country roots looking fab in this Panama hat featuring a rhinestone string, wide brim, and faux wool material. Complete the look in a cute long sleeve dress.

Fit & Features
- Rhinestone string
- Wide brim
- Faux wool material
Style Number/Barcode: 07302-0476

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Key To Style Crop Top
Unlock your stunning style with a top that is perf for creating your latest looks! The top features a crew neckline, a small keyhole at the bust, long sleeves, and a cropped hem. The top is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with high-waist jeans.

Fit & Features
- Crew neckline
- Keyhole at the bust
- Long sleeves
- Crop fitted hem
- Lined brushed knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4229

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Slithering Chic Snake Three Pack Ring Set
You're in for a slithering chic look with this ring set featuring rhinestone insets on geo and snake designs. Complete the look in a glam faux fur jacket.

Fit & Features
- Three pack set
- Rhinestone embellishments
- Geo and snake designs
Style Number/Barcode: 07004-0249

Category Name: Vacation Looks

Price: $5.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Winter Florals Ruched Bodycon Dress
Florals for winter? Absolutely! This bodycon dress features a sleeveless, bungee spaghetti strap on a scoop neck, ruched sides, and a fitted hem. Composed of soft-knit fabric with a moderate stretch. Perfect for styling with a moto jacket.

Fit & Features
- Sleeveless, bungee spaghetti straps
- Scoop neck
- Ruched sides, fitted hem
- Floral pattern throughout
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4445

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sophisticated Marble Fan Metal Earrings
Go for a sophisticated style in these dangly earrings featuring a marble stone accent, a fan metal bottom, and a rubber back stopper for a secure fit. Complete the look in an oversized blazer.

Fit & Features
- Marble stone accent
- Fan metal bottom
- Rubber back stopper
Style Number/Barcode: 07001-1243

Category Name: Vacation Looks

Price: $0.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Showstopper Cutout Ruffle Slit Maxi Dress
Serve major allure in this sleeveless maxi dress while on vacay or weekend getaway! The maxi dress delivers a sultry design with a twist plunge V-neckline, cutout bodice, and a high front slit with a ruffled trim.

Fit & Features
- Slinky knit fabric, short knit lining
- Plunge twist V-neckline
- Shoulder straps, one metal accent piece
- Cutout bodice
- High front slit with ruffle trim
- Bodycon maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-4070

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fan Dance Stone Accent Earrings
Show up to the party in these dangly earrings featuring a multi-pattern stone accent, a metal fan bottom with a back rubber stopper for a secure fit. Complete the look with a sleek clutch.

Fit & Features
- Multi-pattern stone accent
- Metal fan bottom
- Back rubber stopper
Style Number/Barcode: 07001-1244

Category Name: Vacation Looks

Price: $1.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Thinking About Knit Cutout Midi Dress
You've got knit on the mind, show off in a midi dress that stuns! The dress features a crew neckline, short sleeves, a knot accent at the center with dual cutouts at the waist, and a midi-length silhouette that is accented with a high side slit. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a clutch.

Fit & Features
- Crew neckline
- Short sleeves
- Twist knot accent
- Dual cutouts at the waist
- Midi-length silhouette, high side slit
- Cotton knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4261

Category Name: Vacation Looks

Price: $19.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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