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.

Flutter And Fly Butterfly Earrings
Flutter and fly into these chic earrings featuring rhinestone butterfly charms along the dainty chain links and a post-back closure. Complete the look in a flirty skater dress.

Fit & Features
- Rhinestone butterfly charms
- Dainty chain links
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1343

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Fling Twist Slit Maxi Skirt
So much for a summer fling! With this maxi skirt, you're sure to fall for it over and over again. It features a high-rise waist with a twist accent, a front high-cut slit, and a form-fitting silhouette on lined knit fabric. Complete your look with the matching top.

Shop Matching Top: Summer Fling Twist Front Crop Top

Fit & Features
- High-rise waist with twist accent
- Front high-cut slit
- Form-fitting silhouette
- Maxi-length hem
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0673

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tequila And Friends Graphic Tee
Haven't you heard? You in this graphic tee plus friends equals one great night! It features short sleeves, a crew neck, a front script that reads, "Tequila And Friends Make A Great Blend", and a cropped hem. Complete the look in sleek skinny pants and heels.

Fit & Features
- Short sleeves
- Crew neck
- Front graphic with "Tequila And Friends Make A Great Blend"
- Cropped hem
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06002-1398

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Two Moods Sweater Knit Halter Top
Why blend in when you can stand out in this sweater halter top featuring a sleeveless, two-toned bodice, tie-back neck closure, a partial open-back, and a cropped hem on stretchy rib-knit fabric. Complete the look in boyfriend jeans.

Fit & Features
- Sleeveless, halter neck
- Tie-back neck closure
- Two-toned bodice
- Partial open-back
- Cropped hem
- Sweater rib-knit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1492

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summertime Glam Slide-On Sandals
Bring that glam vibe you love to your casual summertime look! These slide-on sandals feature a round toe, a dual banded strap design with braided woven detailing in a trendy metallic hue, and a flat sole. Style with your fave summer dress and sleek hoops.

Fit & Features
- Slide-on fit
- Round toe
- Dual banded strap design, braided woven detailing, metallic hue
- Flat sole, faux leather material
- Runs true to size
Style Number/Barcode: 07404-1073

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Give A Twirl Linen Skater Dress
Have your twirl-worthy moment in this linen skater dress perfect for casual parties! It features three-quarter-length puff sleeves with ruffled hems, a square neckline, a babydoll-style seam, a flirty open-back with an elasticized lattice strap, and a short-length hem with a flared-out skater silhouette. Complete the look in this skater dress with strappy stiletto heels.

Fit & Features
- Three-quarter-length puff sleeves, ruffled elastic cinched hems
- Square neckline
- Babydoll style seam
- Open-back, elasticized lattice strap
- Short skater silhouette
- Plaid linen fabric, lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4717

Category Name: Vacation Looks

Price: $5.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On An Adventure Corduroy Utility Romper
This corduroy romper will inspire your next adventure! It features short sleeves, a collared neckline, front zipper closure and flap pockets, an adjustable belted waist with belt loop accents, back pockets, and a form-fitting silhouette. Complete the look in cool sunglasses and thigh-high boots.

Fit & Features
- Short sleeves
- Collared neckline
- Front zipper closure and flap pockets
- Adjustable belted waist, belt loop accents, back pockets
- Form-fitting silhouette
- Corduroy fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06303-0168

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Country Chic Faux Suede Romper
Look chic in the countryside in this faux suede romper showcasing a flirty silhouette with a front twist accent, sleeveless v-neckline, spaghetti straps, and flowy shorts. Complete the look with a straw hat for wine tasting.

Fit & Features
- Sleeveless, v-neckline
- Spaghetti straps
- Front twist accent
- Flowy shorts
- Faux suede fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-1004

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Finders Keepers Chiffon Romper
Lucky you to have found this chiffon romper for keeps! It features a sleeveless, square neck, spaghetti straps, an open tie-back design, high waist seam, and a ruffled overlay with shorts lining. Complete your trendy look in espadrille wedges.

Fit & Features
- Sleeveless, square neck
- Spaghetti straps
- Open tie-back design
- High waist seam
- Ruffled overlay, shorts lining
- Airy chiffon lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06403-0243

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bloom Baby Floral Halter Cutout Mini Dress
Soft, flirty, and ready for golden hour—this halter mini dress is a little bit sweet, a little bit daring. Flowy ruffles and a smocked waist keep the vibe effortlessly pretty for sunset dinners or dressy events!

Fit & Features
- Floral print, chiffon woven fabric, woven lining
- Sweetheart twist halter neckline, tie straps
- Cutout bust accent
- Stretchy, smocked, fitted bodice
- Drop waist seam
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000243

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Night Out Crepe Romper
Have a chic night out in this alluring crepe romper! It features a sleeveless square neckline, spaghetti straps, an open back with a tie-back design, a front waist cutout, and fitted shorts with an envelope skirt overlay. Style with strappy mules and a sleek clutch.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open-back, tie-back design
- Front waist cutout
- Fitted shorts, envelope skirt overlay
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1010

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Just A Slice Cutout Crop Top
You know you'd like to have a slice of this cami crop top! It features a sleeveless, v-neck, spaghetti straps, and cut-out accents along the front on brushed knit fabric with a moderate stretch. Perfect for layering under a sheer top for an eye-catching look.

Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Cut-out accents along the front
- Cropped hem
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4360

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Dress Code Mesh Marble Crop Top
The dress code this season calls for this mesh marble crop top paired with your fave bottoms! It features long sleeves, a square neck, and dual tie-front closures that add eye-catching detail. Complete the look in wide-leg pants and heels.

Fit & Features
- Long fitted sleeves
- Square neck
- Dual tie-front closures
- Cropped hem
- Marble print
- Sheer mesh fabric, front knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4348

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mary Tie-Waist Mini Skirt by Windsor Denim
Create adorable everyday looks with the Mary mini skirt by Windsor Denim! It features a high-rise waist, a trendy tie-front belt, a mini-length frayed hem, and a form-hugging fit. The denim fabric offers minimal stretch. Style with a fitted bodysuit and strappy mules.

Fit & Features
- High-rise waist
- Tie-front belt
- Mini-length frayed hem
- Form-hugging fit
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06601-0060

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Everyday Essential Racerback Tank Top
This soft brushed knit tank top is an everyday essential you can dress up or down! It features a sleeveless scoop neckline, tank shoulder straps with a racerback design, and a mid-length, form-hugging fit. Style with your fave pair of denim and slides for a cute and casual look.

Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps, racerback design
- Mid-length, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1184

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Leo Jersey Graphic Tee
Let this graphic tee do the talking! It features classic cap sleeves, a crew neck, a front script that reads, "Leo Give Me Space & Attention", and a cropped hem on smooth jersey knit fabric. Complete the look in a sleek mini skirt for a birthday celebration.

Fit & Features
- Cap sleeves
- Crew neck
- Front script reads, "Leo Give Me Space & Attention"
- Cropped hem
- Smooth jersey-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1404

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Rare Marble Pattern Midi Dress
Why blend in when you can stand out! Strut into the party in this marble midi dress featuring a trendy, sleeveless, square neck, bungee spaghetti straps, and a bodycon silhouette. Complete the look in doorknocker earrings.

Fit & Features
- Sleeveless, square neck
- Bungee spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Marble pattern
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4723

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Out Of Office Ruched Mini Dress
Log off and get ready for a relaxing getaway in this ruched knit mini dress. It features a sleeveless cowl neckline, spaghetti straps, ruching down one side leading to an adjustable drawstring, and a mini-length, asymmetrical hem. The smooth knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals and your favorite shades.

Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- High waist seam
- Ruching down one side seam, adjustable drawstring
- Short, curve-hugging, bodycon silhouette, asymmetrical hem
- Stretchy knit fabric, tropical palm leaf print
- Runs true to size
Style Number/Barcode: 05102-4691

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sparks Fly V-Neck Crop Top
Sparkle and shine in this glam yet subtle crop top featuring short sleeves, a V-neck with rhinestone bar accents, and a fitted hem on rib-knit fabric. Complete the look in a sleek mini skirt for a dinner date.

Fit & Features
- Short sleeves
- V-neck
- Rhinestone bar accents
- Crop fitted hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1342

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Made To Be Seen PU Halter Crop Top
This PU crop top is made to be seen! Step out in this edgy-chic top featuring a sleeveless, halter plunge neckline, lace-up corset-style bodice, partial open-back, and zipper closure. Complete the look in 90's-inspired jeans for a girl's night.

Fit & Features
- Sleeveless, halter plunge neckline
- Lace-up, corset-style bodice
- Cropped hem
- Partial open-back
- Zipper closure
- PU fabrication
- Fits true to size
Style Number/Barcode: 06003-1789

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Rockstar Life Graphic Crop Top
Have the times of your life in this graphic crop top featuring an edgy, one-shoulder neckline with dual chain-link straps, front graphic detail with "Born To Be A Rockstar" script along the fitted, crop hem. Complete your cool look with new sunglasses.

Fit & Features
- Sleeveless, one-shoulder neckline
- Dual chain-link straps
- Front graphic detail with "Born To Be A Rockstar" script
- Fitted crop hem
- Cotton fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1363

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Jazz Night Twist Front Crop Top
Enter the room of the rhythm and blues! All eyes on you in this saucy crop top featuring a sleeveless, sweetheart neck, adjustable spaghetti straps, and a twisted bust, on pleated-lined fabric. Complete the look in the matching bottoms.

Shop Matching Bottoms: Jazz Night High Rise Pants

Fit & Features
- Sleeveless, sweetheart neck
- Adjustable spaghetti straps
- Twisted bust
- Cropped hem
- Pleated-lined fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4527

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
New Fling Crepe Strapless Jumpsuit
Bold meets femme in the crepe strapless jumpsuit perfect for showcasing a new look this season! It features a tube-style bodice, pleated neckline, high-waist seam, form-hugging, and a straight-leg silhouette. Complete the look in a chic necklace for a party.

Fit & Features
- Sleeveless, strapless
- Tube-style bodice, pleated neckline, flexible boning
- High-waist seam, back zipper closure
- Form-hugging
- Straight-leg silhouette
- Crepe fabrication, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-1631

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Fantasy Strapless Cutout Maxi Dress
Easy to wear, impossible to forget! Make your entrance in this floral maxi dress designed with a flirty cutout and form-hugging fit that accentuates your figure.

Fit & Features
- Floral print, mesh-lined fabric
- Strapless neckline
- Cutout bodice
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000079

Category Name: Vacation Looks

Price: $9.97 $39.90

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