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.
HomeVacation Looks
Vacation Looks
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.
-
Effortless Blis Sleeveless Bodycon Knit Midi Dress
Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.
Fit & Features
- Unique knit fabric, stretchy knit lining
- Adjustable spaghetti straps
- Square neckline, bust tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5712
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dreamy Vacay Tropical Print Woven Romper
Look like you're ready to jet-set off to a dreamy vacay in this bold tropical print romper! The lightweight woven fabric is accented with an abstract tropical palm leaf print with bright hues perf for sunny days by the water. The romper features a sleeveless sweetheart neckline with a dainty eyelet lace trim, a ruched bust with a tie-front detail, thin tank straps that lead to a smocked back for added stretch, a fitted high waist, and flowy shorts for a relaxed look. Style with strappy sandals!
Fit & Features
- Abstract tropical print
- Woven fabric with top knit lining, eyelet lace trim
- Sweetheart neckline, ruched bust, tie-front detail
- Thin tank straps, stretchy smocked back, zipper with hook and eye closure
- Fitted high waist, flowy shorts
- Runs true to size
Style Number/Barcode: 06403-0462
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Babe Gingham Print Side Tie Bikini Bottoms
Channel that flirty babe style in these adorable gingham printed side tie bikini bottoms with a dainty eyelet trim. Pair with one of the matching bikini tops for a sweet and sassy look.
Shop Matching Tops: Flirty Babe Gingham Print Triangle Bikini Top, Flirty Babe Gingham Print Bandeau Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- Gingham print
- Eyelet trim
- High-cut design, side tie closures
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0865
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stunning Silhouette Bodycon Midi Dress
Show off a stunning silhouette in this sleek knit midi dress featuring a sleeveless square neck, ruching to flaunt your figure, and a hanky hem with a chic flared fit. Style with stilettos for cocktail hour!
Fit & Features
- Smooth knit fabric, high stretch, stretch knit lining
- Sleeveless square neckline
- Spaghetti straps
- Ruching
- Bodycon silhouette
- Midi-length hanky hem
- Runs true to size
Style Number/Barcode: 05101-4112
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: SAGE, HUNTER, LIGHT, MARSALA, BROWN
Available Size: XS, S, M, L, XL
-
Just A Girl Mid-Rise Striped Boxer Skort
You're just a girl who loves to look cute and casual, and this striped boxer skort is just the ticket! With a flattering mid-rise waist with button accents and a form-hugging fit, you'll love having this skort in the lineup.
Fit & Features
- Striped print, woven fabric
- Elasticized mid-rise waist, button accents
- Form-hugging fit
- Shorts lining
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06303-000024
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fall Favorite Turtleneck Braided Sleeve Sweater
Look no further for your new favorite turtleneck sweater this season! It features long sleeves with an eye-catching braided design, a cropped hem, and is crafted from a soft rib knit fabric perfect for keeping cozy and cute. Complete the look in a trendy pleated mini skirt for a coffee date and movie!
Fit & Features
- Long sleeves, braided design
- Turtleneck
- Cropped hem
- Soft rib knit fabric
- Runs true to size
Style Number/Barcode: 06005-1751
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Everyday Style Short Sleeve Ruched Mini Dress
Level up your everyday style with this simple yet chic mini dress! The lightweight smooth nylon fabric includes a knit lining and offers plenty of stretch for ultra-comfortable wear. Shaped with a classic scoop neckline and short sleeves, the mini-length dress features ruching down the side seams to flaunt your figure on the bodycon silhouette. Pair with a denim jacket and sneakers.
Fit & Features
- Smooth nylon fabric with knit lining, plenty of stretch
- Scoop neckline
- Short sleeves
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5669
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Charming Appeal Puff Sleeve Eyelet Knit Skater Dress
The sweet eyelet design and adorable details give this puff sleeve skater dress a charming appeal! Made with an airy sheer eyelet knit fabric with a partial knit lining, this short dress is perfect for your spring and summer weekend outings. It features a square neckline with chic ruching at the bust, sheer short puff sleeves with a dainty ruffled trim, a sheer corset-style bodice to create a cinched look, and a fit-and-flare skater silhouette for a flirty vibe. Complete your outfit with hoop earrings!
Fit & Features
- Sheer eyelet knit fabric, partial knit lining, plenty of stretch
- Square neckline with ruched bust
- Sheer short puff sleeves, ruffled trim, elastic cinched hems
- Sheer corset-style bodice, stretchy high waist seam
- Fit and flare skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5427
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Casual Stand Out Faux Leather Suede Sneakers
Are you looking to make your casual 'fits stand out? These sneakers feature a round toe and lace-up placket for the perfect fit. The faux suede pattern adds a touch of contrast while the rubber sole provides traction. Crafted from sleek faux leather, these sneakers are a must-have! Style with a trendy denim jumpsuit for weekend plans!
Fit & Features
- Round toe
- Lace-up placket
- Faux suede contrast pattern
- Rubber traction sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07407-0224
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Greetings From Mallorca Graphic Tee
A cute knit tee to pack with you on vacay! It boasts a front graphic with a script that reads "Greetings From Mallorca" and a fitted crop hem perfect for styling with high-rise bottoms.
Fit & Features
- Stretchy cotton-blend knit fabric
- Crew neckline
- Short sleeves
- Front graphic, script reads "Greetings From Mallorca"
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000038
Category Name: Vacation Looks
Price: $22.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Glam Squad Faux Leather Rhinestone Sneakers
Make any outfit shine in these fashion sneakers! With a round toe, rhinestone embellished lace-up placket and tongue, a platform rubber sole, and a sleek faux leather upper, these sneakers are perfect for stepping out with your glam squad. Complete the look in a smooth knit dress to elevate your style for day or night plans!
Fit & Features
- Round toe
- Rhinestone-embellished lace-up placket
- Rhinestone embellished tongue
- Platform rubber sole
- Faux leather upper
- Cushioned footbed
- Runs true to size
Style Number/Barcode: 07407-0218
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Jetset Babe One Shoulder Tropical Maxi Dress
Jetset off on vacation like a babe in this tropical maxi dress! With a flirty and flattering one-shoulder neckline, ruched seams, and a bodycon silhouette, you'll be turning heads. Plus, the side slit and maxi-length hem add a touch of allure. Complete the look in sandals and sunglasses.
Fit & Features
- Tropical palm leaf print, stretchy knit
- One shoulder neckline
- Bodycon silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5702
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Give Me Cozy Half-Zip Fuzzy Knit Crop Sweater
Cozy up in this fuzzy knit sweater for warm cuddles all day and a cute look! The sweater features slouchy long sleeves with ribbed cuffs, a half-zipper front closure, a foldover collar neckline, and a cropped rib hem. Style with high-rise jeans for school or casual weekend plans!
Fit & Features
- Slouchy long sleeves with ribbed cuffs
- Half-zipper front closure
- Foldover collar neckline
- Cropped rib hem
- Fuzzy knit sweater fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1757
Category Name: Vacation Looks
Price: $3.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt
Sweet and flirty, this floral ruched mini skirt will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The skirt features a high-rise elasticized waist, a ruched seam with an adjustable drawstring for a customized fit, a short front slit, and a bodycon silhouette. Style with the matching tie-front top for a day date!
Shop Matching Top: Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top
Fit & Features
- Ditsy floral printed knit fabric, moderate stretch
- High-rise elasticized waist
- Ruched seam with adjustable drawstring
- Short slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1005
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunny Escape Stiletto Mules
These raffia mule heels bring breezy, sun-soaked energy with breezy midi dresses or cute denim skirts perfect for any sun-soaked day.
Fit & Features
- Stiletto heel
- Square toe
- Braided strap
- Cushioned insole
- Raffia woven material
- Runs true to size
Style Number/Barcode: 07401-000533
Category Name: Vacation Looks
Price: $30.90
Availability: In Stock
Available Color: BEIGE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
-
Cozy Weather Faux Fur Bucket Hat
This adorable faux fur bucket hat is a cozy must-have for your cold-weather 'fits! It features a classic bucket hat design composed of an ultra-plush faux fur material with a smooth woven lining. Style with a sherpa-lined jacket for all the comfy vibes this season!
Fit & Features
- Classic bucket hat design
- Short brim
- Faux leather material
- Woven interior
Style Number/Barcode: 07302-1568
Category Name: Vacation Looks
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Classic bucket hat design
-
Cold Babe Faux Sherpa Block Heel Booties
Strut like a babe in these cozy faux leather booties! They feature a square-shaped toe, an inner zipper closure, a platform sole, a tall block heel, and a soft faux sherpa trim to help keep you warm on chilly days. Complete the look with a cozy jacket.
Fit & Features
- Square toe
- Inner zipper closure
- Platform sole
- Tall block heel
- Faux sherpa trim
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1681
Category Name: Vacation Looks
Price: $12.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Layer Up Sleeveless Puffer Vest With Pockets
Style up your look in this puffer vest for the chilly season ahead! Featuring a sleeveless design with a standing collar neckline, front zipper closure, and an elasticized cropped hem. Crafted with an insulated nylon woven fabric and hidden side pockets with snap-button closures for extra comfort and warmth. Complete the look in a basic long sleeve top and jeans for a coffee run and errands!
Fit & Features
- Sleeveless standing collar neckline
- Front zipper closure
- Hidden side pockets with snap-button closures
- Elasticized cropped hem
- Insulated nylon woven fabric for warmth
- Puffer design
- Runs true to size
Style Number/Barcode: 06201-0428
Category Name: Vacation Looks
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Casual And Chill Plaid Shacket
Keep it casual and chill with a shacket that brings those girl-next-door vibes. The shacket features a plaid print, a multi-button down front, two chest pockets, long sleeves with a single-button cuff, and a longline length with a rounded hem. The shacket is composed of a soft faux wool fabric that offers a relaxed fit with a minimal stretch. Complete the look with thigh-high boots.
Fit & Features
- Plaid print
- Collared neckline
- Long sleeves with button cuff
- Multi-button down front
- Two chest pockets
- Longline length, rounded hem
- Faux wool fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1657
Category Name: Vacation Looks
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Better Half Cable Knit One Shoulder Sweater Top
Wrap up in cozy style with this cable knit sweater top perfect for looking effortlessly cute in the chilly season! It features a one-shoulder neckline, a slouchy long sleeve with ribbed cuffs, a cropped hem, and a soft cable knit design. Complete the look in a faux leather mini skirt and boots for a coffee date.
Fit & Features
- One-shoulder neckline
- Slouchy long sleeve, ribbed cuffs
- Cropped hem
- Soft cable knit design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1746
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Golden Hour High-Rise Cargo Wide-Leg Linen Pants
Stroll in these linen wide-leg pants during golden hour on vacation or a weekend by the beach! Designed with a high-rise elasticized waistband and linen fabric, these pants are perfect for all-day wear along with convenient cargo flap pockets and a wide-leg silhouette, you'll feel effortlessly chic and ready for anything. Complete the look with the matching vest and sandals.
Shop Matching Vest: Golden Hour Tie-Front Linen Vest
Fit & Features
- Linen fabric lined with stretchy knit
- High-rise elasticized waistband
- Cargo flap pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0810
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Best Feeling Scoop Neck Cutout A-Line Midi Dress
There's nothing better than enjoying a sunny day in this scoop neck midi dress! With adjustable straps and a stretchy smocked bodice with a flirty cutout, this dress offers the perfect look for any occasion. The A-line silhouette and midi-length hem add a touch of playful style. Complete the look with dainty earrings and sandals.
Fit & Features
- Modal blend woven fabric with lining
- Adjustable spaghetti straps
- Scoop neckline
- Stretchy smocked bodice with cutout
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5718
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Effortless Chic Acrylic Bangle Bracelet
Effortless style you can slip right on. This acrylic bangle bracelet nails that chunky, laid-back look—perfect for stacking or rocking solo.
Fit & Features
- Acrylic material
- Thick bangle silhouette
- Slip-on design
Style Number/Barcode: 07003-000122
Category Name: Vacation Looks
Price: $4.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Floral Sensation High Waist Pants
Keep it sensational in floral pants this season! The pants feature a high-rise waist, a ditsy floral print, and a wide leg hem. Complete look with the matching crop top.
Shop Matching Crop Top: Floral Sensation Off The Shoulder Top
Fit & Features
- High rise waist
- Wide leg hem
- Ditsy floral print
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06502-0608
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale