Vacation Looks
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.
Now Trending
STYLE SPOTLIGHT
Get Eye-Catching Sandals For Women
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.
-
Gorgeous Sparkle Layered Necklace
Showcase a gorgeous sparkle with this embellished layered necklace. It features a three-row layered design. The shortest layer features a chain-link design with thin clear glass stones at the center, and the two longer layers feature mini rhinestone embellishments. Style this necklace with simple stud earrings.
Fit & Features
- Three-row layered design
- Shortest layer features a chain-link design, thin clear glass stones at the center
- Two longer layers feature mini rhinestone embellishments
- Adjustable chain, lobster clasp closure
Style Number/Barcode: 07002-1273
Category Name: Vacation Looks
Price: $5.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cozy Mood Striped Knit Sweater
You'll be in a totally cozy mood in this adorable striped knit sweater! It features a crew neckline, long dolman-style sleeves, distressed detailing at the hems, and a mid-length, relaxed fit. The thick knit fabric has minimal stretch. Style with dark wash denim and ankle boots.
Fit & Features
- Crew neckline
- Long dolman-style sleeves
- Distressing at the hems
- Mid-length, relaxed fit
- Striped pattern
- Knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1597
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Fresh And Chic Crossbody Purse
This sleek faux leather crossbody purse will make your everyday 'fits fresh and chic. It features a rectangular shape with a curved design at the bottom, a fold-over with snap-button closure, and a chain-link and faux leather shoulder strap. Style with hoop earrings.
Fit & Features
- Rectangular shape, bottom curved design
- Fold-over with snap-button closure
- Chain-link and faux leather shoulder strap
- Spacious and lined interior
- Faux leather material
Style Number/Barcode: 07203-1065
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Everyday Glam Rhinestone Ring Set
This trendy rhinestone ring set is perfect for that everyday glam vibe! The pack features six rings including one statement ring and five thin dainty rings, all with rhinestone embellishments. Style this set with sleek hoop earrings.
Fit & Features
- Six-pack metal ring set
- One statement ring
- Five thin band rings
- Rhinestone embellishments
Style Number/Barcode: 07004-0303
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
90s Chick Boyfriend Denim Jacket
Take it back to a 90s chick look with this boyfriend denim jacket featuring long sleeves with button cuffs and drop shoulder seams, a collar neckline, button-down closures, front flap pockets, and a cropped hem with a cinched elastic back band. Perfect for styling with high-rise jeans.
Fit & Features
- Long sleeves, button cuffs, drop shoulder seams
- Collar neckline
- Button-down closures
- Front flap pockets
- Cropped hem, cinched elastic back band
- Medium-wash denim fabric
- Runs true to size
Style Number/Barcode: 06203-0449
Category Name: Vacation Looks
Price: $17.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Posh And Pleated Long Sleeve Crop Top
Posh and pleated, this long sleeve crop top is a fall must-have. It features a deep V-neckline, long peasant sleeves, a cinched front design with a drawstring, and a cropped, form-hugging fit. The trendy pleated knit fabric offers a moderate stretch. Style with faux leather pants and heels.
Fit & Features
- V-neckline
- Long peasant sleeves
- Cinched front, drawstring
- Cropped hem
- Pleated detailed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4524
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
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