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.

Sun Dance Paisley Flare Pants
Dance all day in these boho flare pants featuring a high-rise elasticized waist, form-fitting silhouette, and a paisley multi-print design. Complete the look in a wrap crop top.

Fit & Features
- High-rise elasticized waist
- Form-fitting
- Flared hem
- Boho paisley print
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0920

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Beachy-Chic Bodycon Mini Dress
Showcase a beachy-chic vibe in this curve-hugging bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, form-fitting silhouette. The stretchy brushed knit fabric features an all-over tropical palm leaf print. Style this dress with espadrille sandals.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching down the side seams
- Mini-length, form-fitting, bodycon silhouette
- Tropical palm leaf print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4696

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Flower Lattice Back Dress
Look as pretty as the island flowers in this tropical maxi dress perfect for a luau dinner! It features a sleeveless, square neck, sleek spaghetti straps, an open back with lattice detailing, a sultry side slit, and a curve-hugging silhouette. Complete your vacay look in large hoop earrings.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back, lattice straps
- Side slit, curve-hugging silhouette
- Maxi-length hem
- Tropical floral print, knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4506

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Get That Glitzy Glow Bikini Top
Get that glitzy glow for your weekend getaway with this trendy bikini top! It features a basic triangle design with halter spaghetti straps, tie-back straps, and a lurex glitter mesh fabric with sheer mesh inserts. Complete the look with the matching bikini bottoms.

Shop Matching Bottoms: Get That Glitzy Glow Bikini Bottoms

Fit & Features
- Triangle design
- Halter spaghetti straps
- Tie-back spaghetti straps
- Lurex glitter mesh fabric, sheer mesh inserts
- No padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0697

Category Name: Vacation Looks

Price: $8.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In Line High Rise Striped Pants
These woven striped pants should be in line with your summer aesthetic! They feature a high-rise waist, side pockets for keeping your hands warm, and a wide-leg silhouette. Complete the look in the matching top.

Shop The Matching Top: In Line Tie-Front Striped Top

Fit & Features
- High-rise waist
- Side pockets
- Wide-leg silhouette
- Striped woven fabric
- Fits true to size
Style Number/Barcode: 06302-0621

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
In Line Tie-Front Striped Top
This woven striped top should be in line with your summer aesthetic! Featuring kimono-style short sleeves, a tie-front design, and a cropped hem. Complete the look in the matching pants.

Shop Matching Bottoms: In Line High Rise Striped Pants

Fit & Features
- Kimono-style short sleeves
- Tie-front design
- Cropped hem
- Striped woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1220

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sassy Retro Cat Eye Sunglasses
Sassy and retro! These oversized sunglasses feature cat-eye sleek metal frames, tinted gradient lenses, rubber most supports, and arms. Complete the look in a printed jumpsuit for a party.

Fit & Features
- Oversized style
- Cat-eye sleek metal frame
- Tinted gradient lenses
- Rubber nose supports and arms
- 100% UV protection
Style Number/Barcode: 07008-0952

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paradise Ready One-Shoulder Maxi Dress
This gorgeous tropical printed maxi dress will have you looking ready for a vacay off to paradise! It features a sleeveless one-shoulder neckline, a single bungee spaghetti strap, an asymmetrical waist cutout with a chic O-ring accent, and a curve-hugging, floor-length silhouette with a front slit. The stretchy knit fabric features an all-over palm leaf print. Complete your look with slip-on sandals and your fave shades.

Fit & Features
- Sleeveless one-shoulder neckline
- Single bungee spaghetti strap
- Asymmetrical waist cutout, O-ring accent
- Maxi-length hem, form-fitting silhouette, front slit
- Tropical palm leaf print
- Knit fabric, short knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4484

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Hopping Tropical Maxi Dress
Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.

Fit & Features
- Sleeveless, halter neck with tie
- Cutout bodice
- Open-back, tie closure
- Side slit
- Flowy maxi silhouette
- Tropical print, woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 05102-4500

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Away On Vacay Tropical Mini Dress
Going away on vacation? This tropical mini dress will definitely get you in the vacay mood! It features a sleeveless, scoop neck, spaghetti straps, a form-hugging silhouette, and a side ruched seam that leads to the asymmetrical slit hem. Complete the look in chic oversized sunnies.

Fit & Features
- Sleeveless, scoop neck
- Spaghetti straps
- Form-hugging silhouette
- Side ruched seam, asymmetrical slit hem
- Mini-length
- Tropical print, sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4682

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Desert Vacay Sleeveless Maxi Dress
Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.

Fit & Features
- Sleeveless plunging V-neck and back design
- Tank shoulder straps
- High-rise banded waist, side cutouts
- Maxi-length hem, flowy silhouette
- Front slit
- Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4504

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Summer Halter Maxi Dress
Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.

Fit & Features
- Sleeveless, halter neck, tie closure
- O-ring inset, cutout accent
- Bodycon silhouette
- Asymmetrical slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4467

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Effect Abstract Cowl Halter Crop Top
Printed to perfection in a flattering halter silhouette, this crop top boasts a sultry cowl neckline and an open back to show some skin! Pair with the matching pants.

Fit & Features
- Abstract print, stretchy knit fabric
- Cowl halter neckline, tie straps
- Open back
- Fitted crop hem
- Runs true to size
Shop The Matching Pants: Sultry Effect Abstract Wide-Leg Pants
Style Number/Barcode: 06001-000107

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Kaleidoscope Boho Tie-Front Top
Escape the city life for paradise with this boho crop top featuring a sleeveless, sweetheart neck, adjustable spaghetti straps, a tie-front detail, back smocked design, and a kaleidoscope print. Complete the look in the matching skirt.

Shop Matching Skirt: Kaleidoscope Boho Slit Maxi Skirt

Fit & Features
- Sleeveless, sweetheart neck
- Adjustable spaghetti straps
- Tie-front detail
- Back smocked design
- Kaleidoscope boho print
- Runs true to size
Style Number/Barcode: 06003-1556

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Playful Twist Halter Knit Romper
This halter romper comes with a playful twist! Featuring a sleeveless, keyhole halter neckline with cross straps, tie closure, a partial open-back, high-rise waist, and a flowy short hem. Complete the look in chic espadrille wedges.

Fit & Features
- Sleeveless, halter neckline, tie-closure
- Cross front straps, keyhole
- Partial open-back
- Flowy short hem
- Sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-0995

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Kaleidoscope Boho Slit Maxi Skirt
Escape the city life for paradise with this boho maxi skirt featuring a high-rise waist, front high-cut slit, and a kaleidoscope print. Complete the look in the matching top.

Shop Matching Top: Kaleidoscope Boho Tie-Front Top

Fit & Features
- High-rise waist
- Front high-cut slit
- Maxi-length hem
- Kaleidoscope boho print
- Runs true to size
Style Number/Barcode: 06301-0103

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Love It Lace-Up Crop Top
You'll love this lace-up crop top that is an elevated version of your fave basic tanks. It features a sleeveless square neckline, spaghetti straps, a lattice-front design, and a cropped, form-hugging fit. Style with high-rise denim and cute mules.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up front, tie closure
- Cropped fit
- Woven fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-1861

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortless And Chic Cropped Blouse
This effortless and chic cropped blouse is a stunning summer staple! It features a sweetheart neckline with a lace-up tie-front design, half-length bishop sleeves, ruched detailing, and a cropped fit. Style with high-rise denim.

Fit & Features
- Sweetheart neckline
- Lace-up tie-front design
- Half-length sheer bishop sleeves, elasticized hems
- Ruching
- Back zipper closure
- Cropped fit
- Sheer woven fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06003-1878

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ready For The Weekend Tube Top
You'll be ready for a relaxing weekend getaway with this cute cropped tube top. It features a strapless sweetheart neckline, a front lace-up design, and a majorly cropped hem. Complete the look with the matching flowy pants and strappy sandals.

Shop Matching Bottoms: Ready For The Weekend Flowy Pants

Fit & Features
- Strapless sweetheart neckline, no-slip strip
- Front lace-up design, tie closure
- Cropped, form-hugging fit
- Textured woven fabric, front lining, no stretch
- Runs true to size
Style Number/Barcode: 06003-1880

Category Name: Vacation Looks

Price: $21.90

Availability: Out of Stock
Product Badge:
- Sale
Time For The Weekend Denim Catsuit
This trendy denim catsuit will have you totally weekend-ready! It features a sleeveless halter neckline, side cutouts that lead to the back, a high-rise waist, and a form-hugging fit throughout the leg. Style this catsuit with strappy mules and chic shades.

Fit & Features
- Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
- Back zipper, hook and eye closure
- Side cutouts that lead to the back
- High-rise waist, back zipper, hook and eye closure
- Form-hugging fit
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0344

Category Name: Vacation Looks

Price: $10.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Gorgeous Getaway Sleeveless Maxi Dress
Get ready for a gorgeous getaway in this alluring sleeveless maxi dress! It features a V-neckline, spaghetti straps, a cross-back strap design, a fitted high waist seam, and a floor-length silhouette with a chic high front slit. The knit fabric features an all-over tropical palm leaf print. Style this dress with strappy sandals.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back strap design
- Fitted high waist seam
- Floor-length silhouette, high front slit
- Palm leaf print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-4362

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chloe High Rise Distressed Denim Shorts By Windsor Denim
Showcase your best assets in the Chloe high-rise denim shorts by Windsor Denim perfect for a warm-weather day! She features a flattering high-rise waist, trendy distressed accents along the front and back, a roll cuff raw hem, and is composed of premium light wash denim fabric with a form-hugging fit and moderate stretch. Complete the look in a crop top and mules.

Fit & Features
- High-rise waist
- Distressed accents along the front and back
- Roll cuff raw hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Light wash denim fabric, moderate stretch
- Form-hugging and fits true to size
Style Number/Barcode: 06603-0249

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
In The Shade Straw Floppy Hat
Shield your eyes from the sun's rays in this straw floppy hat perfect for styling with a gorgeous sundress! It features a rounded top with a large floppy brim. Complete the look with a pair of chic shades.

Fit & Features
- Rounded top
- Large floppy brim
- Straw material
Style Number/Barcode: 07302-1382

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Perfect Nubuck Strap Sandals
These flat sandals are so perfect for everyday style! They feature an almond toe, nubuck multi-strap design, faux leather footbed, and slide-on/off styling. Complete the look in a casual bodycon dress for a coffee date.

Fit & Features
- Almond toe
- Nubuck multi-strap design
- Faux leather footbed
- Slide-on/off styling
- Runs true to size
Style Number/Barcode: 07404-1009

Category Name: Vacation Looks

Price: $11.97 $16.90

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