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.

Trendy Glitz Rhinestone O-Ring Chain Belt
This rhinestone O-ring chain belt will give your looks that trendy glitz! It features a bold O-ring linked design embellished with sparkling rhinestones for pretty glamour. Includes a back adjustable chain with a lobster clasp closure. Layer this belt over a mini dress, a blazer, a mini skirt, or dress pants!

Fit & Features
- Large O-ring linked design
- Front rhinestone embellishments
- Back adjustable chain, lobster clasp closure
Style Number/Barcode: 07301-0697

Category Name: Vacation Looks

Price: $4.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tied In Cozy Chenille Tie-Waist Robe
Tie yourself up in this cozy chenille robe perfect for lounging around! The robe features long sleeves, an open-front design, a tie-waist belt, front pockets for keeping your hands warm, and a mid-length hem on ultra-soft chenille knit fabric. Complete the look in the matching pajama top and bottoms for a chill night!

Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top

Shop Matching Pajama Bottoms: Fuzzy Feels Chenille High-Rise Jogger Pajamas

Fit & Features
- Long sleeves
- Open-front design
- Tie-waist belt, front pockets
- Mid-length hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0942

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hello Cutie Chenille Crop Pajama Top
Look and feel like a cutie in this chenille pajama top! The tank top features a sleeveless square neckline, tank-style straps, and a cropped hem on ultra-soft and cozy knit chenille fabric. Complete the look in the matching pajama bottoms and robe for the perfect lounge sesh!

Shop Matching Pajama Bottoms: Fuzzy Feels Chenille High-Rise Jogger Pajamas

Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe

Fit & Features
- Sleeveless square neckline
- Tank-style straps
- Cropped hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0938

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feeling The Vibe High-Rise Chenille Joggers
Feel the cozy vibes in these chenille joggers perfect for lounging on the weekend! The jogger pants feature a high-rise elastic drawstring waist, a skinny jogger-style leg, and are crafted from ultra-soft and stretchy chenille rib knit fabric. Complete the look in the matching pajama top and cardigan for the perfect lounge sesh!

Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top

Shop Matching Cardigan: Cuddle Time Chenille Crop Cardigan

Fit & Features
- High-rise elastic drawstring waist
- Skinny jogger-style leg
- Ultra-soft chenille rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0947

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Autumn Chill Crochet Wide-Leg Pants
You'll love styling these crochet knit pants on chill autumn days! They feature a flattering high-rise elasticized waistband, a wide-leg silhouette, and ribbed cuffs. Complete the look in a basic top, cozy jacket, and slippers!

Fit & Features
- High-rise elasticized waistband
- Wide-leg silhouette
- Ribbed cuffs
- Crochet knit fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06502-2392

Category Name: Vacation Looks

Price: $5.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Frolic In Floral Tie Midi Dress
Frolic all over town in this floral midi dress perfect for an afternoon tea with the girls! It features a sleeveless V-neck, spaghetti straps, a knot tie bust, a curve-hugging silhouette, and a flirty front slit. The dress is designed with a ditsy floral bud print on stretchy knit fabric. Complete the look in trendy wedge sandals.

Fit & Features
- Sleeveless V-neck
- Spaghetti straps
- Knot tie bust
- Curve-hugging silhouette
- Front slit, midi-length hem
- Ditsy floral bud print, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4865

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stop And Flare Smocked Skater Dress
Stroll on by making everyone stop and stare at you in this flirty skater dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a cutout bust accent, a stretchy smocked bodice, and a flattering skater short-length hem. Complete the look in statement sandals for a brunch or day date!

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Cutout bust accent
- Stretchy smocked bodice
- Skater silhouette, short-length hem
- Cotton fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5337

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Something Special Lace Satin Tie Skater Dress
Look and feel like something special in this lace skater dress and enter your romance era! The dress features a sweetheart neckline with a satin ribbon tie, an underwire bust for support, adjustable satin spaghetti straps, and a satin ribbon tie waist that leads to the flattering skater silhouette and ruffled short-length hem. Complete the look in sparkly sandals for a day date or party!

Fit & Features
- Sleeveless sweetheart neckline, satin ribbon tie
- Underwire bust, adjustable satin spaghetti straps
- Back zipper and hook-eye closure
- Satin ribbon tie waist
- Skater silhouette, ruffled short-length hem
- Delicate sheer lace, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5336

Category Name: Vacation Looks

Price: $9.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Caught On-Trend Basic V-Neck Midi Dress
Get caught on trend always in this basic midi dress for casual slays! It features cap sleeves, a V-neckline, a flattering bodycon silhouette, and a midi-length hem on soft modal knit fabric with a stretchy mesh lining. Complete the look with a ring set and heels.

Fit & Features
- Cap sleeves
- V-neckline
- Bodycon silhouette
- Midi-length hem
- Soft modal knit fabric, stretchy mesh lining
- Runs true to size
Style Number/Barcode: 05102-5306

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Serious Chills Velour Cargo Joggers
Sit back and chill or go on a coffee run in these trendy velour joggers! It features a flattering mid-rise elasticized waist with hidden side pockets for keeping your hands warm, a relaxed fit, cargo flap pockets, and elasticized cuffs. The ultra-soft velour fabric has a moderate stretch. Complete the look with the matching jacket and your favorite sneakers!

Shop Matching Jacket: Serious Chills Velour Zip Up Hoodie Jacket

Fit & Features
- Mid-rise elasticized waist
- Hidden side hip pockets
- Cargo flap pockets, velcro closures
- Relaxed fit
- Elasticized cuffs
- Soft velour fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0973

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Colorful Sensation Abstract Print Maxi Dress
Be the colorful sensation in whatever room you walk into wearing this abstract print midi dress! It features a sleeveless square neckline, spaghetti straps, a bodycon silhouette, and an adjustable ruched drawstring atop a sultry slit. Complete the look with a chic handbag for an art gallery opening or sunset cocktails!

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Adjustable ruched drawstring, high slit
- Maxi-length hem
- Abstract print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5279

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Artsy Dreamer One Shoulder Abstract Maxi Dress
Dreaming of an artsy wardorbe? Look no further than this abstract print maxi dress perfect for an art show or gallery opening! It features a sleeveless one-shoulder neckline, tank strap, a bodycon silhouette, and a side ruched seam atop a sultry high slit to show some skin. Complete the look with a rhinestone bracelet and heels.

Fit & Features
- Sleeveless one-shoulder neckline, tank strap
- Bodycon silhouette
- Side ruched seam, high side slit
- Maxi-length hem
- Abstract print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5258

Category Name: Vacation Looks

Price: $5.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Shine All Way Metallic Woven Skater Dress
Shine all way to and from the party in this breezy skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a stretchy smocked waist, and a flattering skater silhouette with a ruffled short-length hem. The dress is crafted from an airy woven fabric with shimmering metallic threads and has a stretchy knit lining. Complete the look in stiletto heels.

Fit & Features
- Sleeveless V-neck
- Adjustable spaghetti straps
- Stretchy smocked waist
- Skater silhouette
- Ruffled short-length hem
- Metallic threads, airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5405

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Timeless Staple Mid-Rise Button Denim Skort
All buttoned up, this mid-rise denim skort is a true timeless staple.

Fit & Features
- Medium wash denim fabric
- Mid-rise waist
- Button-up front closures
- Form-hugging fit, shorts bottom
- Mini-length hem
- Back pockets, belt loop accents
- Runs true to size
Style Number/Barcode: 06603-0486

Category Name: Vacation Looks

Price: $7.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stunning Standout Marble Print Satin Midi Dress
You'll be a stunning standout in this silky-satin marble print midi dress! It features a sleeveless sweetheart neckline with a sultry bust seam outline, adjustable spaghetti straps, waist cutouts on each side that lead to an open lower back, and a midi-length hem with a flowy A-line silhouette. The sleek satin-woven fabric features a multi-colored marble print pattern for an eye-catching vibe. Complete your look for happy hour with stilettos.

Fit & Features
- Sleeveless sweetheart neckline, bust seam outline
- Adjustable spaghetti straps, stretchy smocked back panel
- Dual waist cutouts, lead to an open lower back
- High waist, hidden side zipper, hook and eye closure
- Midi-length hem, flowy A-line silhouette
- Marble print, silky satin-woven fabric, top knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2892

Category Name: Vacation Looks

Price: $44.90

Availability: Out of Stock
Product Badge:
- Sale
Carpe Denim Platform Block Heels
Seize the day in these majorly trendy denim platform heels! They feature an almond toe, crisscross straps, a chunky platform sole and block heel, and an adjustable ankle strap with buckle closure. Complete the look with a chic mini handbag for a party.

Fit & Features
- Almond toe
- Crisscross straps
- Chunky platform sole and block heel
- Adjustable ankle strap, buckle closure
- Denim material
- Runs true to size
Style Number/Barcode: 07401-4516

Category Name: Vacation Looks

Price: $12.96 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ray Of Beauty Ruffled Short Skater Dress
You'll be a bright ray of beauty in this adorable ruffled short skater dress! It features a V-neckline with a cute tie-front design, a front keyhole cutout, short puff sleeves with a ruffled trim, a high-rise stretchy smocked waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight sheer chiffon fabric includes a partial woven lining. Style with hoop earrings and clear mules for a day date!

Fit & Features
- V-neckline, tie-front design, front keyhole cutout
- Short puff sleeves, ruffled trim
- High-rise stretchy smocked waist
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Sheer chiffon fabric, partial woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5392

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Picking Daisies Chiffon Strappy Skater Dress
The perfect dress you'll want to pluck from the garden! This dreamy skater dress features adorable puff short sleeves, a square neckline, and pleated bust, a cutout strappy front and back with ties, and a short-length hem on daisy printed chiffon fabric. Complete the look in cute sandals for a family party!

Fit & Features
- Puff short sleeves
- Square neckline, pleated bust
- Cutout strappy front and back, tie closure
- Back hidden zipper and hook-eye closure
- Skater-silhouette, short-length hem
- Dainty printed chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5389

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Forever Basic Crew Neck Slit Midi Dress
Forever your basic midi dress with head-turning detail! It features classic cap sleeves, a crew neckline, a flirty cutout back accent, a flattering bodycon silhouette, and a midi-length hem with a high front slit. The soft brushed knit fabric has plenty of stretch. Complete the look with a glam ring set for a family party or casual date!

Fit & Features
- Cap sleeves
- Crew neckline
- Cutout back accent
- Bodycon silhouette
- Midi-length hem, high front slit
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5334

Category Name: Vacation Looks

Price: $5.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Contemporary Art Hoop Earrings
Elevate your contemporary style with these artsy hoop earrings for the perfect finishing touch! They feature a sleek metal hoop frame with a U-shaped dip and horizontal lines from side to side. Complete the look with a sleek choker necklace for brunch or a theatre show!

Fit & Fetaures
- Sleek metal frame
- Hoop design
- U-shaped dip
- Horizontal lines from side-to-side
- Fish hook-clasp closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1670

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Work Or Play Ruffle Strap Button Skater Dress
Work or play, this cotton skater dress is a charming choice for a stroll downtown or a coffee date! It features a sleeveless V-neckline, adorable ruffled straps, a stretchy smocked bodice, a button-down front, and a flattering short-length hem. Complete the look in strappy heels.

Fit & Features
- Sleeveless V-neckline
- Ruffled straps
- Stretchy smocked bodice
- Button-down front
- Skater silhouette, short-length hem
- Lightweight cotton fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5369

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sheer Elegance Mesh Tie Front Kimono
Layer on sheer elegance to your look with this mesh kimono perfect for a beach day or weekend escape! It features three-quarter length sleeves, a V-neckline, tie-front closure, and a cropped hem on sheer mesh fabric. Complete the look in chunky sandals.

Fit & Features
- Three-quarter length sleeves
- V-neckline
- Tie-front closure
- Cropped hem
- Sheer mesh fabric
- Runs true to size
Style Number/Barcode: 06202-0311

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Divine Darling Square Neck Ruffle Mini Dress
Breeze in looking so darling in this sleeveless mini dress for a day date or dinner party! It features a square neckline, adjustable spaghetti straps, an eye-catching tie-back closure, and a flattering wrap hem with ruffle trim. The dress is composed of an airy woven fabric with a stretchy knit lining. Complete the look with strappy block heels.

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tie-back closure
- Wrap mini-length hem, ruffle trim
- Airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2860

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Chill Crew Neck Knit Dress
You'll feel effortlessly chill in this basic midi dress perfect for looking cute on the go! It features short sleeves, a crew neck, a bodycon silhouette, a side slit accent, and a knee-length hem. The dress is composed of a soft hacci rib knit fabric with plenty of stretch. Style with trendy flat sandals for grabbing coffee!

Fit & Features
- Short sleeves
- Crew neck
- Bodycon silhouette
- Side slit accent
- Knee-length hem
- Hacci rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5190

Category Name: Vacation Looks

Price: $9.97 $20.90

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