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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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.

Country Glow Rhinestone Panama Hat
Glow up the night in the countryside in this Panama hat featuring a circle rhinestone trim, and a wide brim, and is composed of faux wool material. Complete the look in cute cowgirl boots.

Fit & Features
- Rhinestone trim
- Wide brim
- Panama style
- Faux wool material
Style Number/Barcode: 07302-1340

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Getaway Girlie Halter Bead Crochet Mini Dress
Your next getaway calls for this crochet mini dress! This dress has a stunning halter bead neckline that adds a touch of boho, a cutout accent, and a flattering bodycon silhouette.

Fit & Features
- Crochet lined fabric
- Halter beaded neckline, spaghetti strap ties
- Padded bra cups
- Back zipper hook-eye closure, lower ruched seam
- Cutout front accent
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6116

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cozy Cable Knit Tie-Front Mini Dress
Bring all the cozy vibes this season in this adorable cable knit mini dress! It features a V-neck and back with wrap designs, long balloon sleeves with tapered hems, a high waist with a tie-front accent, and a short, form-hugging fit. Style with knee-high boots.

Fit & Features
- V-neck and back, wrap design
- Long balloon sleeves, tapered hems
- High waist seam, tie-front
- Mini-length hem, form-hugging fit
- Cable knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4842

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Color Me Pretty Ombre Midi Dress
Give your closet some pretty color with this ombre knit midi dress perfect for dressing up! The dress features a sleeveless scoop neck, sleek spaghetti straps, an open lace-up back with tie closure, a bodycon silhouette, and an asymmetrical side slit cutout to showcase some chic strappy heels.

Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Open lace-up back, tie closure
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Ombre lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4825

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fur Baby Pom Knit Beanie
Cozy up this fall to winter in this faux fur pom beanie featuring a swirl knit design and a cuffed hem on cozy fabric. Complete the look in a denim jacket and booties.

Fit & Features
- Faux fur pom
- Swirl knit design
- Cuffed hem
- Cozy and soft fabric
Style Number/Barcode: 07302-1320

Category Name: Vacation Looks

Price: $1.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Quilted Verdict Crossbody Bag
The verdict of this patent leather crossbody bag is that you must have it! The bag features an adjustable chain link strap, front turn-lock closure, a spacious interior, and a quilted design on patent faux leather material. Complete the look in a strappy crop top.

Fit & Features
- Adjustable chain link strap
- Front turn-lock closure
- Spacious interior
- Quilted design
- Patent faux leather material
Style Number/Barcode: 07203-0997

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glisten Girl Rhinestone Pom Beanie
Glisten, girl, wherever you go in this rhinestone beanie featuring a faux fur tonal pom, ribbed-knit design, and a cuffed hem. Complete the look in a cozy jacket.

Fit & Features
- Rhinestone embellishments
- Faux fur tonal pom
- Ribbed-knit design
- Cuffed hem
Style Number/Barcode: 07302-0950

Category Name: Vacation Looks

Price: $6.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Draw Attention One-Shoulder Midi Dress
You'll draw all the attention to you in this one-shoulder midi dress perfect for a casual lunch with friends! The dress features a single long sleeve, an adjustable drawstring waist cutout, a side ruched seam, and a form-hugging fit. Complete the look in chic lattice booties.

Fit & Features
- One-shoulder neckline
- Single long sleeve
- Adjustable drawstring waist cutout
- Side ruched seam
- Form-hugging, midi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4803

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty In Ombre Rib Knit Sweater
Color yourself in this pretty ombre rib knit sweater featuring long sleeves, ribbed cuffs and crew neck, and an oversized silhouette. Complete the look in straight-leg jeans for a casual coffee date!

Fit & Features
- Long sleeves
- Ribbed cuffs and crew neck
- Oversized silhouette
- Ombre pattern
- Rib-knit design
- Fits true to size
Style Number/Barcode: 06005-1565

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chill In The Air Zip Puffer Jacket
Bundle up in this stylish crop puffer jacket to brace the chilly air! It features long sleeves with elasticized cuffs, a collar neckline, zipper closure, and elasticized hem. The jacket is composed of iridescent nylon-woven fabric with insulation to help keep you warm and protected from the elements. Complete the look in cool lug booties.

Fit & Features
- Long sleeves with elasticized cuffs
- Collar neckline
- Zipper closure
- Elasticized crop hem
- Iridescent nylon-woven fabric
- Insulated and lined
- Fits true to size
Style Number/Barcode: 06201-0348

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Plaid's My Favorite Woven Skirt
It's the season for cozy layers and your favorite print! This plaid woven skirt features a high-rise waist, back zipper closure, bodycon silhouette, and a mini-length hem. Complete the look with the matching shacket.

Shop The Matching Shacket: Plaid's My Favorite Woven Shacket

Fit & Features
- High-rise waist
- Back zipper closure
- Bodycon silhouette
- Mini-length hem
- Plaid pattern, woven fabric
- Fits true to size
Style Number/Barcode: 06401-0460

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coffee Date Chic Plaid Scarf
This adorably chic plaid scarf is perfect for your fall coffee dates! It features a large oblong design, a soft brushed knit fabrication with fringe detailing, and an all-over plaid print pattern. Style with hoop earrings and a crossbody purse.

Fit & Features
- Large oblong design
- Brushed knit fabrication, no stretch
- Fringe detailing
- Plaid print
Style Number/Barcode: 07305-0422

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Autumn Air Turtleneck Knit Sweater
Brace the autumn air in this cozy and cute turtleneck knit sweater featuring long sleeves with drop shoulder seams and a relaxed silhouette. Complete the look in new jeans and booties for a fall festival!

Fit & Features
- Long sleeves with drop shoulder seams
- Turtleneck
- Relaxed silhouette
- Ribbed knit design
- Fits true to size
Style Number/Barcode: 06005-1544

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bundle Up Plaid Blanket Scarf
Bundle up in this classic plaid scarf that is perfect for the fall and winter seasons! It features a large blanket design with an all-over fringe hem and a chic plaid pattern. Style with a belted trench coat and booties.

Fit & Features
- Large blanket design
- Soft knit fabrication, no stretch
- Fringe hem
- Plaid pattern
Style Number/Barcode: 07305-0424

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cuddle Weather Plaid Blanket Scarf
Cuddle up with this adorable plaid blanket scarf! It features a soft knit fabrication with trendy fringe detailing and an all-over plaid print pattern. Style with a sweater dress and knee-high boots.

Fit & Features
- Large blanket design
- Knit fabrication, no stretch
- Fringe detailing
- Plaid print
Style Number/Barcode: 07305-0429

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Totally Crushing A-Line Mini Dress
A crush-worthy strapless mini dress you'll love styling for every occasion! You'll love the flattering A-line fit of this short tube dress, while the ruffled mini hem adds a touch of playful charm.

Fit & Features
- Smooth knit stretchy fabric
- Strapless neckline
- A-line silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000112

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cold Weather Glam Faux Fur Gloves
Enter into the cold season in a glamorous style with these rhinestone gloves featuring faux fur cuffs and lining, with a smooth faux suede exterior. Complete the look in an oversized blazer.

Fit & Features
- Rhinestone embellishments
- Faux fur cuffs and lining
- Smooth faux suede exterior
Style Number/Barcode: 07304-0028

Category Name: Vacation Looks

Price: $4.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Western Chic Faux Leather Cowboy Hat
Top off your fall looks with this faux leather cowboy hat that brings those western chic vibes! It features a band accent, a curved brim, and a smooth PU material. Style with knee-high boots.

Fit & Features
- Band detail
- Curved brim
- PU material
Style Number/Barcode: 07302-1351

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Be Dazzled Rhine Over The Knee Boots
These rhinestone over-the-knee boots will dazzle you! They feature an almond toe, block heel, side zipper closure, and a high shaft with an adjustable drawstring so you can customize the fit. Complete your glam look in a sleek LBD for date night or a concert!

Fit & Features
- Almond toe
- Block heel
- Side zipper closure
- Over the knee length
- Adjustable drawstring
- Rhinestone embellishments
- Runs true to size
Style Number/Barcode: 07402-0816

Category Name: Vacation Looks

Price: $12.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Futuristic Faux Leather Mini Skirt
Chanel an out-of-this-world style in this faux leather mini skirt featuring a sleek high-rise waist, back zipper closure, side pleated seam, bodycon fit, and an asymmetrical wrap hem. Complete the look in a beaded bustier.

Fit & Features
- High-rise waist
- Back zipper closure
- Side pleated seam
- Bodycon silhouette
- Asymmetrical wrap mini hem
- Faux leather fabric, lining, minimal stretch
- Fits true to size
Style Number/Barcode: 06401-0494

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual Slay Wide-Leg Cargo Pants
Showcase a casual slay in these trendy cargo pants! They feature a high-rise waist, front snap-button, zipper closure, four-pocket styling, and a wide-leg silhouette, composed of a smooth non-stretch woven fabric—style with a crop top and sneakers for an effortless everyday look.

Fit & Features
- High-rise waist, elasticized back
- Dual front snap-buttons and hidden zipper closure
- Belt loop accents
- Side pockets, cargo-style flap pockets
- Wide-leg silhouette
- Smooth woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0683

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ahead Of The Herd Cow Print Jacket
You'll be ahead of the herd in this stylish cow print jacket featuring long sleeves, a collar neckline, flap pockets, open-front design, trucker-style, cropped hem on faux fur fabric. Complete the look in chunky booties.

Fit & Features
- Long sleeves
- Collar neckline
- Flap pockets
- Trucker style
- Cropped hem
- Faux fur fabric, cow print
- Fits true to size
Style Number/Barcode: 06201-0305

Category Name: Vacation Looks

Price: $12.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
West Side Geo Trim Boater Hat
Kick your style up a notch in this western-inspired boater hat. It features a unique geo trim, a wide brim, and faux wool material. Complete the look in a crop top and boyfriend jeans.

Fit & Features
- Geo trim
- Wide brim
- Classic boater style
- Faux wool material
Style Number/Barcode: 07302-0514

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
City Bound Panama Hat
Top off your chic look for a trip to the city with this faux wool panama hat. It features a structured top, a faux leather puffy braided trim, and a wide flat brim. Style with a crossbody purse.

Fit & Features
- Structured top
- Faux leather puffy braided trim
- Wide flat brim
- Faux wool material
Style Number/Barcode: 07302-1349

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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