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.

Off Duty Muse Abstract Print Cutout Jumpsuit
This abstract print jumpsuit is giving effortless icon with a touch of drama. The cutout details and slinky mesh feel made-for-you, perfect for late-night plans or a statement day 'fit.

Fit & Features
- Mesh fabric, high stretch
- Abstract print
- Sleeveless cowl neckline
- Halter tie-back spaghetti straps, metal O-ring accents, partially open back
- Waist cutout, metal O-ring accent
- Curve-hugging fit, flared hem
- Runs true to size
Style Number/Barcode: 06502-000053

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: L
Product Badge:
- Sale
Set To Amaze Mock Neck Abstract Mini Dress
Everyone will admire your amazing self in this abstract mini dress all over town! Made with a unique abstract print on airy lined mesh fabric, this dress is sure to turn heads. The sleeveless design and mock neckline add a chic touch, while the ruched side seams, bodycon fit, and mini-length hem show off your curves. Complete the look with earrings.

Fit & Features
- Abstract print
- Sheer mesh fabric with knit lining, plenty of stretch
- Mock neckline
- Ruching
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5783

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cutest Babe Wide Leg Linen Trouser Pants
No work and all play are the vibes of these linen trouser pants perfect for casual days out to catching your flight out of town! These must-have linen pants feature a flattering high-rise waist, convenient side pockets to keep your phone or hands warm, and a wide-leg silhouette. Complete the look in the matching cropped vest or corset and sandals.

Shop Matching Tops:
Cutest Babe Halter V-Neck Corset Crop Top
Cutest Babe Strapless Linen Bustier
Cutest Babe Button Up Linen Vest

Fit & Features
- Linen-blend woven fabric
- High-rise waist
- Front button and hidden zipper closure
- Side pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0811

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Out Of Town Strapless Floral Crepe Mini Dress
The perfect floral crepe mini dress to take with you out of town! Boasting a strapless neckline, this mini-length dress has a trendy contrast foldover design and a bodycon silhouette that flatters your curves. Complete the look in sandals and sunnies!

Fit & Features
- Floral print, crepe fabric lined with stretchy knit
- Contrast foldover design
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3364

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweeten Me Up Flutter Sleeve Tie Front Crop Top
Sweeten your every day in this adorable flutter sleeve crop top on any casual occasion! Featuring playful flutter short sleeves, a trendy tie front design, and a cute ruffled crop hem, this top is perfect for adding a touch of fun to any outfit. Complete the look in jeans and block heels.

Fit & Features
- Woven fabric, no stretch
- Flutter short sleeves
- Tie front design
- Ruffled crop hem
- Runs true to size
Style Number/Barcode: 06204-1825

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Poolside Flirt Eyelet String Bikini Bottoms
Sit flirty and pretty in this eyelet string bikini bottom at a pool party or on vacation! Pair with the matching bikini top.

Fit & Features
- Eyelet lined fabric
- Low-rise waist
- Dual string spaghetti ties
- Cheeky coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Shop The Matching Bikini Top: Poolside Flirt String Bikini Top
Style Number/Barcode: 07105-0866

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paradise Pick V-Neck Cutout Tropical Maxi Dress
Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.

Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline, keyhole
- Cutout back
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5692

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Points Of Interest Triangle Print Strap Flat Sandals
Step out in style in these faux leather flat sandals. These sandals feature a round toe and a woven strap with a quirky triangle print, perfect for adding a touch of fun to your outfit while the faux leather flat sole ensures all-day comfort. Complete the look with a trendy handbag.

Fit & Features
- Round toe
- Faux leather flat sole
- Woven strap with triangle print
- Runs true to size
Style Number/Barcode: 07404-1221

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Summer Nights Boho Halter Satin Crop Top
Sunny days and sultry nights call for this boho satin crop top! The halter neckline and spaghetti strap tie provide a secure and comfortable fit, while the open back and lower tie closure add a touch of daring. With its pointed crop hem, this top is perfect for pairing with your favorite high-waisted bottoms.

Fit & Features
- Boho print, satin fabric, stretchy knit lining
- Halter neckline with spaghetti strap tie
- Open back with lower tie closure
- Pointed crop length hem
- Runs true to size
Style Number/Barcode: 06003-2558

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always A Vibe Basic Knit Tank Top
This basic tank top is always a vibe! With a sleek square neckline and form-hugging fit, this top is essential for creating cute fits'.

Fit & Features
- Stretchy knit fabric
- Square neckline
- Wide shoulder straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000027

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
50s Icon Halter Plunge Neck Skater Romper
Chanel a popular 50s iconic look in this halter plunge skater romper perfect for themed parties or summer holidays! With a flattering halter neckline and charming tie closure, this romper will create a stunning silhouette. The skater shape and short hem add to its playful appeal. Complete the look with hoop earrings.

Fit & Features
- Smooth cotton-blend knit fabric, moderate stretch
- Halter plunge neckline, tie closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06503-1138

Category Name: Vacation Looks

Price: $44.90

Availability: In Stock

Available Color: BLACK, BROWN

Available Size: XS, S, M, L
All Time Favorite Strappy Metallic Flat Sandals
Discover your new favorite pair of metallic sandals! They feature a chic square toe and a strappy design that will elevate any outfit. And with their flat sole and metallic faux leather material, they provide a chic and comfortable style. Complete the look with a tote purse.

Fit & Features
- Square toe
- Flat sole
- Strappy design
- Metallic faux leather material
- Runs true to size
Style Number/Barcode: 07404-1084

Category Name: Vacation Looks

Price: $8.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish In The Chill Puffer Jacket
Keep stylish through the chill in this quilted puffer jacket featuring long sleeves with buttoned cuffs, a collar neckline, snap-button down front closures, flap pockets, and a cropped hem. The jacket is designed with thin insulation to help keep you comfortable and protected from the elements. Style over a long sleeve top with woven joggers.

Fit & Features
- Long sleeves, buttoned cuffs, collar neckline
- Snap-button down front closures
- Flap pockets
- Cropped hem
- Quilted thin puffer woven fabric
- Insulated and lined
- Fits true to size
Style Number/Barcode: 06201-0317

Category Name: Vacation Looks

Price: $17.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Distressed High Waist Cut-Off Denim Shorts
These trendy distressed high waist cut-off denim shorts are a summer closet staple! Made with a stretchy cotton-blend denim fabric, they feature a flattering high-rise waist, a fitted silhouette, distressed detailing, and a frayed cut-off hem for an edgy vibe. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jean shorts with a crop top and sneakers.

Fit & Features
- Cotton-blend denim fabric, moderate stretch
- High waist
- Fitted
- Distressing, frayed cut-off hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Runs true to size
Style Number/Barcode: 06603-0377

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Serve Looks Square Sunglasses
Serve nothing but cute looks in these square sunglasses for UV protection and stylish flair!

Fit & Features
- Square frames
- Tinted colored lenses
- 100% UV protection
Style Number/Barcode: 07008-000015

Category Name: Vacation Looks

Price: $9.90

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Babe Strapless Lace-Up Striped Crop Top
Level up your summer 'fits like the bold babe you are with this strapless lace-up crop top! Made with a striped ribbed knit fabric, it offers plenty of stretch. The tube top features a strapless straight-across neckline, a trendy lace-up front with an alluring cutout design and tie closure, and a cropped hem with a form-hugging fit for that snatched look. Style with wide-leg pants for a chic vibe.

Fit & Features
- Stretchy striped ribbed knit fabric
- Strapless straight neckline
- Lace-up front with tie closure
- Cropped
- Fitted
- Runs true to size
Style Number/Barcode: 06002-1867

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beauty On Vacay Cutout Abstract Maxi Dress
From seaside dinners to dancing under the moonlight, this abstract print maxi dress will have you looking like a beauty on the island! It features delicate spaghetti straps, a sweetheart neckline with an O-ring bust insert, a cutout bodice to reveal some skin, and a flattering bodycon silhouette and maxi-length hem. Complete the look with strappy wedges.

Fit & Features
- Abstract print, knit fabric, short knit lining
- Spaghetti straps
- Sweetheart neckline
- O-ring bust insert, cutout
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5584

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep It Light High Rise Linen Palazzo Pants
Keep it light and effortless in these high-rise linen palazzo pants for a day spent under the sun! With a high-rise waist and side pockets, these pants offer both a flattering fit and convenience. The palazzo wide-leg silhouette keeps you comfortable, while the linen fabric elevates the look. Style with the matching top.

Shop Matching Top: Keep It Light Sleeveless Linen Corset Top

Fit & Features
- Linen woven fabric, no stretch
- High-rise waist, stretchy smocked back waistband
- Pockets
- Palazzo wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0815

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Never Blend In Butterfly Chain Necklace
Never blend in but stand out in this butterfly chain necklace secured with a lobster clasp closure. Complete the look in high heels for a dressy occasion.

Fit & Features
- Butterfly charms
- Chain link
- Lobster clasp closure
Style Number/Barcode: 07002-1864

Category Name: Vacation Looks

Price: $3.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Staple Ribbed Knit Bandeau Top
This casual ribbed knit bandeau top is a staple style to have in your closet. Pair with your fave high-rise bottoms or layered under cute tops!

Fit & Features
- Stretchy ribbed knit fabric
- Strapless straight neckline
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07109-000001

Category Name: Vacation Looks

Price: $6.97 $12.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK, WHITE

Available Size: M/L, S/M
Product Badge:
- Sale
Next Chapter High-Rise Carpenter Denim Shorts
Write your next stylish chapter in these high-rise denim shorts! With a high-rise waist and form-hugging fit, these shorts accentuate your curves while providing comfort. Plus, the bottom side strap and mini pocket add a unique touch to the medium-wash denim fabric. Complete the look in a graphic tee for casual plans!

Fit & Features
- Medium wash denim, slight stretch
- High rise waist
- Form-hugging fit
- Bottom side strap and mini pocket accent
- Front button and hidden zipper closure
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-0368

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breezy Energy Tie Front Long Sleeve Linen Top
This linen crop top boasts breezy energy for effortless summer styling! Featuring stylish bell sleeves and a trendy tie-front design, this top will elevate your fashion game. The cropped hem adds a modern touch. Complete the look in a denim mini skirt and sandals.

Fit & Features
- Linen blend fabric, no stretch
- Bell long sleeves
- Tie-front design
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1760

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Watch Me Bloom Off-The-Shoulder Floral Midi Dress
Be the talk of any garden party in this floral midi dress! The off-the-shoulder neckline exudes femininity, while the cutout waist shows some skin. The flowy midi-length silhouette and front slit offer a trendy allure. Complete the look in lace-up heels and earrings.

Fit & Features
- Floral print, woven fabric with lining, no stretch
- Off-the-shoulder neckline
- Cutout waist
- Front slit
- Flowy midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3414

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hot Cowgirl Summer Trucker Hat
Embody the country vibes in this trucker hat all season! It features a classic curved wide brim, an embroidered script that reads "Hot Cowgirl Summer" and a mesh back with adjustable snap-back closures. Complete the look in a denim jumpsuit.

Fit & Features
- Curved wide brim
- Embroidered script reads "Hot Cowgirl Summer"
- Mesh back with adjustable snap-back closures
Style Number/Barcode: 07302-1649

Category Name: Vacation Looks

Price: $4.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials