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.

Festive Medallion Flare Pants
Get ready for the festival season in these boho flare pants featuring a high-rise elasticized waist, form-fitting silhouette, and a unique medallion border print on brushed knit fabric with plenty of stretch. Complete the look in a chic panama hat.

Fit & Features
- High-rise elasticized waist
- Form-fitting silhouette
- Flared hem
- Medallion borderprint
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-0851

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Paisley Babe Flare Pants
These paisley flare pants are total babe status! They feature a high-rise elasticized waist and a form-fitting silhouette on brushed knit fabric with a moderate stretch. Complete the look in a flirty tie-front top.

Fit & Features
- High-rise elasticized waist
- Form-fitting silhouette
- Flared hem
- Paisley print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-0844

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Reese High Rise Denim Shorts By Windsor Denim
Laidback and chill, you'll the Reese high-rise denim shorts by Windsor denim! They feature a vintage-inspired silhouette with a trendy roll cuffed hem on medium wash denim fabric. Complete the look in a corset top and sandals.

Fit & Features
- High-rise waist
- Vintage-inspired silhouette
- Roll cuffed hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim fabric, no stretch
- Fits true to size
Style Number/Barcode: 06603-0259

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Cutest Vibe Ditsy Floral Romper
Showcase the cutest vibe this summer season in this ditsy floral printed romper. It features short fitted cap sleeves, a V-neckline, center ruching with an adjustable drawstring, a high waist seam with a front cutout, and flowy shorts. Style this romper with a classic denim jacket and espadrille sandals.

Fit & Features
- Short cap sleeves
- V-neckline
- Center ruched detailing, adjustable drawstring
- High waist seam, front cutout
- Flowy shorts
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06503-0979

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Swept Away Floral Ruffled Maxi Dress
Get swept up in a pretty maxi dress that brings the romance! The dress features a sleeveless sweetheart neckline, tie-up spaghetti straps, tiered ruffles, a floral print, and a maxi-length silhouette. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals and butterfly earrings.

Fit & Features
- Sleeveless sweetheart neckline
- Tie-up spaghetti straps
- Tiered ruffles
- Floral print
- Maxi length silhouette
- Lined lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1101

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet And Chic Paper Bag Shorts
Sweet and chic, these dressy paper bag shorts will elevate your everyday looks. They feature a high-rise waist, a tie-front belt, front pockets, and a relaxed fit. Style with a basic bodysuit or a cute cropped blouse.

Fit & Features
- High-rise elasticized paper bag waist
- Tie-front belt
- Front pockets, single faux back pocket
- Relaxed fit
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0204

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
She's Fab Oversized Sunglasses
Keep your summer look on point with these fab oversized shades! The sunglasses feature a square-shaped thin metal frame with cool ombre lenses. Style with a sleek crossbody purse.

Fit & Features
- Square-shaped thin metal frame
- Ombre lenses
- 100% UV protection
Style Number/Barcode: 07008-0955

Category Name: Vacation Looks

Price: $3.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Minimalistic Glam Huggie Three Pack
Love that minimalistic look? Add these glam huggie earrings to your daily lineup. They feature a set of three pairs two with rhinestone insets and post-back closure and one large solid hoop with omega-back closure. Complete the look in a chic casual dress with a blazer.

Fit & Features
- Three pack set
- Two rhinestone small hoops
- Post-back closure
- One large solid hoop
- Omega-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-1225

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dancing Queen CZ Stone Belly Chain
Dance all night queen! Elevate your swimwear in this belly stone featuring CZ stone charms and an adjustable lobster clasp closure. Complete the look in a boho bikini set.

Fit & Features
- CZ stone charms
- Adjustable lobster clasp closure
- Dainty chain link
Style Number/Barcode: 07002-1203

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
New Frames Cat Eye Sunglasses
Everyone will be checking you in these sunglasses! They feature a sleek metal frame with cat-eye accents, gradient lens, and rubber nose supports for comfortable wear. Complete the look in a trendy sweater dress.

Fit & Features
- Sleek metal frame
- Cat-eye accents
- Gradient lens
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-0933

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Daydream Layered Charm Anklet
Create a tantalizing look with this layered charm anklet featuring a three-row design with rhinestones and coin charms with a lobster clasp closure. Complete the look in a flowy kimono and mini dress.

Fit & Features
- Three-row design
- Rhinestones and coin charms
- Lobster clasp closure
Style Number/Barcode: 07003-0329

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Set the Bar Linen Cutout Mini Dress
This flare mini dress sets the bar high! Showcase your daring side in this sleeveless dress featuring a plunge v-neck on the front and back, a smocked bodice, and side elasticized bar cutouts that lead to a flirty mini-length hem. Complete the look in wedges and dainty earrings.

Fit & Features
- Sleeveless, dual plunge v-neck
- Smocked bodice
- Side elasticized bar cutouts
- Flare mini-length hem
- Linen gauze fabric
- Runs true to size
Style Number/Barcode: 05102-4831

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
One Take V-Neck Ruffle Skater Romper
One take in this skater romper and you'll be so obsessed! With a flirty tie back design and flattering skater silhouette, this romper will be your favorite style for brunch to parties!

Fit & Features
- Knit fabric, moderate stretch
- Adjustable spaghetti straps
- Ruffle V-neckline
- Tie-back design
- Skater silhouette
- Ruffle layered short-length hem
- Runs true to size
Style Number/Barcode: 06503-1142

Category Name: Vacation Looks

Price: $46.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Geneviève Floral Chiffon Wrap Dress
Special Occasion

Wrap yourself in a floral dress that brings romance to your event! Geneviève features a darling floral print, a sleeveless V-neckline, and adjustable spaghetti straps that cross at the back. Her back features a lace-up strap design and an elastic stretch at the lower back that leads to a zipper closure. Her slim-fit waist leads to a flowy wrap silhouette that is accented with a high side slit. She is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with wedges and a clutch for the perfect wedding guest outfit.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, lace-up back
- Back zipper closure
- Floral print
- Wrap silhouette, high side slit
- Lined chiffon fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05002-1889

Category Name: Vacation Looks

Price: $19.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortless Style Moves Midi Dress
Make effortless style moves in this adorably-chic midi dress. It features a sleeveless square neckline with a ruffled trim, thin ruffled shoulder straps, a stretchy smocked bodice, a high waist, and a flowy, midi-length, A-line silhouette with a front slit. Complete the look with espadrille sandals.

Fit & Features
- Sleeveless square neckline, ruffled trim
- Thin ruffled shoulder straps
- Stretchy smocked bodice
- High waist seam, flowy A-line silhouette
- Midi-length hem, front slit
- Lightweight linen fabric, woven skirt lining
- Runs true to size
Style Number/Barcode: 05102-4347

Category Name: Vacation Looks

Price: $12.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Vibes Ditsy Floral Romper
Bring the sweet vibes to your everyday summer look with this adorable romper. It features a sleeveless square neckline, spaghetti straps, a fitted smocked bodice, flowy shorts, and an all-over ditsy floral print pattern. Style this romper with a jean jacket and slip-on sandals.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Smocked bodice, fitted high waist seam
- Flowy shorts
- Ditsy floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0978

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fresh And Flirty Floral Romper
Get a fresh and flirty summertime look with this adorable floral printed romper. It features a sleeveless V-neckline with a tie-front design, spaghetti straps, a front waist cutout, a fitted high waist seam, and flowy shorts with a cute ruffled hem. Style with a denim jacket and strappy sandals.

Fit & Features
- Sleeveless V-neckline, tie-front
- Spaghetti straps
- Front waist cutout
- Fitted high waist seam
- Flowy shorts, ruffled hem
- Floral print, lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0209

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Social Linen Fringe Mini Skirt
Make the plans. Get trendy with your look in this linen mini skirt featuring a high-rise waist, fringed hem, and a bodycon fit. Complete the look in the matching top.

Shop Matching Top: Social Linen Tie Strap Crop Top

Fit & Features
- High-rise waist
- Back zipper, hook and eye closure
- Fringed hem
- Bodycon fit
- Linen-lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0107

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Social Linen Tie Strap Crop Top
Make the plans. Get trendy with your look in this linen tie strap crop top featuring a sleeveless square neckline with adjustable spaghetti straps, fringed crop hem, and a side zipper closure. Complete the look in the matching bottoms.

Shop Matching Bottoms: Social Linen Fringe Mini Skirt

Fit & Features
- Sleeveless, square neck
- Adjustable tie spaghetti straps
- Fringed crop hem, smocked back
- Side zipper closure
- Linen-lined woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1625

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cheetah Daze One Shoulder Bikini Top
Add some spice to your swimwear with this cheetah bikini top featuring a one-shoulder neckline, asymmetrical strap with cutout detail, removable padding on lined fabric. Complete the look in the matching bikini bottoms.

Shop The Matching Bikini Bottoms: Cheetah Daze Cutout Bikini Bottoms

Fit & Features
- Sleeveless, one-shoulder neckline
- Asymmetrical strap, cutout detail
- Removable padding
- Cheetah print
- Lined fabric
- Runs true to size
Style Number/Barcode: 07104-0636

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pool Party High Waist Swim Bottoms
Get the cutest look for all your summer pool parties with these trendy high waist swim bottoms! They feature cutout details on the sides and a semi-cheeky fit. Style with the matching swim top and cool shades.

Shop Matching Top: Pool Party One-Shoulder Swim Top

Fit & Features
- High-rise waist
- Side cutouts
- Semi-cheeky fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0784

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pool Party One-Shoulder Swim Top
Get the cutest look for all your summer pool parties with this trendy one-shoulder swim top! It features an asymmetrical dual strap design with a front cutout detail and removable padding. Style with the matching swim bottoms and cool shades.

Shop Matching Bottoms: Pool Party High Waist Swim Bottoms

Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetrical dual strap design, spaghetti strap, tank strap
- Front cutout detail
- Removable padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0637

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Metallic Moment Bikini Top
Have your moment under the sun! Stun in this sultry bikini top featuring a deep V-neckline, shoulder straps, and a wide bust band. Complete the look in the matching bikini bottoms.

Shop Matching Bikini Bottoms: Metallic Moment Bikini Bottoms

Fit & Features
- Deep V-neckline, shoulder straps
- Wide bust band
- Metallic fabric
- Slip-on/off styling
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0630

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Charm Coin Drop Earrings
These charming boho earrings feature a filigree design, drop accent, and coin charm detailing. Complete the look in a sleek bustier for a night out.

Fit & Features
- Filigree design
- Drop accent
- Coin charm detailing
- Push closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1265

Category Name: Vacation Looks

Price: $3.97 $9.90

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