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.
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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.
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Pixie Low Rise Cut Off Jean Shorts
Oasis by Eunina
Along with high rise jean shorts, a low rise pair is a complete necessity. These Pixie cut offs are a spring and summer staple!
Fit & Features
- Low rise waist
- Traditional five pocket and belt loop design
- Front button | Hidden zipper closure
- Short, majorly frayed hem
- Denim fabric | Moderate stretch
Style Number/Barcode: 06603-0030
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paper Bag Waist Cuffed Jean Shorts
Adorable and oh so flattering, these paper bag waist jean shorts will be your new fave piece of the season!
Fit & Features
- High rise elastic banded paper bag waist
- Dual front buttons | Hidden zipper closure
- Two front and back pockets
- Slight front distressed detailing
- Cuffed hem
- Fitted
- Denim fabric | Moderate stretch
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06603-0042
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tied Up Cropped Knit Top
A little bit cute, a little bit sexy, and a lot of softness! This tie back faux sweater is a good way to transition from winter to spring!
Fit & Features
- Long sleeves that puff at the wrist
- Straight neckline
- Cropped hemline
- Tie back detailing
- Ribbed knit material
- Moderate stretch
Style Number/Barcode: 06001-2402
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beauty In Floral Skater Dress
Beauty, this floral skater dress was made for you! It features a sleeveless bodice, adjustable spaghetti straps, a deep V neckline, a back zipper and hook and eye closure, a tie front belt, and has a flowy skater skirt. The ivory dress is composed of a crepe fabric with a full knit lining and showcases an adorable floral print.Style Number/Barcode: 05102-0278
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Got That Floral Flair Ruched Mesh Dress
You'll have that effortless floral flair in this must have ruched mesh dress!
Fit & Features
- Adjustable spaghetti straps
- Square neckline
- Back zipper | Hook and eye closure
- All over ruched detailing
- Side slit
- Sheer mesh floral printed fabric | Knit lining
- Curve hugging fit
Style Number/Barcode: 05101-0548
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flashy Florals Cut Out Crop Top
Liven up your spring wardrobe with this flashy floral cut out crop top! Make it the star of your 'fit with some basic denim and slide on mules.
Fit & Features
- Long loose sleeves | Elastic banded cuffs
- Sweetheart neckline
- Front O-ring cut out detail
- Front waist cut out
- Cropped | Tie back closure
- All over bold floral print
- Smooth woven fabric | No stretch
Style Number/Barcode: 06003-0764
Category Name: Vacation Looks
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Flirt Floral Bodysuit
Babe, you'll be such a flirt in gorg florals with this effortlessly pretty printed bodysuit!
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- Waist tie front closure
- Knit thong bottom | Dual snap button closures
- Floral printed woven fabric | No stretch
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0740
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tie Dye Satin Midi Skirt
Add a little color to your closet this spring! You can keep it cute and modest doing so when you style a midi skirt with a cowl neck top, and neutral mules!
Fit & Features
- High waist fit
- Stretchy waist line
- Lined
- Over the knee hemline
- Satin with a pastel tie-dye pattern
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06401-0210
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Effortless Tie-Front Ruffled Skater Dress
Make your weekend outfits so effortless with this adorable tie-front skater dress. The lightweight gauze fabric paired with the ruffled skater silhouette creates that breezy, flowy fit you'll love.
Fit & Features
- Gauze woven fabric with smooth woven fabric, no stretch
- Sleeveless V-neckline, padded bust, bust tie accent, keyhole cutout
- Adjustable spaghetti straps
- Partially smocked back
- High waist seam
- Short skater silhouette, tiered ruffled design
- Runs true to size
Style Number/Barcode: 05102-6027
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Borrowed From The Boys Button Front Shirt Dress
A borrowed-from-the-boyfriend inspired look. Cinch that waist with a chic rhinestone encrusted belt!
Fits & Features
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Pointed Collar
- Long Sleeves With Dual Buttoned Cuffs
- Button Down Front
- Curved, High Low Hemline
- Woven Fabric
- Super Relaxed, Boxy Fit
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0761
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pointed Collar
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Time For Change Chain Print Wrap Bodysuit
Sometimes you get that feeling that you want to change up your wardrobe. No need! You just new and different piece to bring you back to life!
Fit & Features
- Wrap style bodysuit
- V-neckline
- Long sleeves with cut out detailing
- Chiffon with chain pattern
- Double snap closure | Cheeky bottom
- Offers stretch at the waist line
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0765
Category Name: Vacation Looks
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Let's Be Sheer Tie Front Top
Transparency is key
Go ahead and pair this with your fave denim cut-offs and some booties! Fits & Features
- Roomy Long Sleeves I Elastic Cuffs
- Tie Front Design
- Crop Hemline
- Mesh Fabric
- Plenty Of Stretch
Black: Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Pink: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06204-0493
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Femme Charm Halter Eyelet Corset Top
Add a touch of femme charm with this eyelet corset top, perfect for sunny-day styling. The top boasts a flirty plunge halter neckline and a cropped hem that flatters your figure.
Fit & Features
- Eyelet fabric, woven lining
- Halter plunge neckline, elasticized strap
- Multiple back hook and eye fasteners
- Flexible boning, crop hem
- Runs true to size
Style Number/Barcode: 06003-000008
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Dream Buttoned Jacket
This button down denim jacket is a total dream! Layer it over your fave spring 'fits.
Fit & Features
- Collared
- Long sleeves with buttons to cuff
- Complete button down front
- Buttoned chest pockets
- Mid-length, form-fitting style
- Jean fabric | Minimal stretch
Style Number/Barcode: 06203-0058
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Day To Night Quilted Chain Backpack
Take your look from day to night with a quilted chain backpack! Perfectly fit more than just the essentials and have that high end vibe!
- Faux leather
- Quilted design
- Chain link straps
- Turn lock front pockets
- Round top zipper closure
- Two inner pockets
Style Number/Barcode: 07203-0266
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On My Way Faux Leather Mini Purse
Whether you are on your way to wedding festivities, a shower, or breakfast with the gals, a light colored faux leather mini purse is the perfect spring outfit topper!
- Mini rectangular structure
- Single handle
- Fold over snap closure
- Faux leather
- Detachable matching shoulder strap
Style Number/Barcode: 07201-0024
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mindin' My Business Wallet Cross-body Purse
Don't mind me, just mindin' my business in my cute lil' wallet purse! Perfectly paired with all closet staples, this cross body purse perfectly fits all ur essentials!
- Mini rectangular design
- Metal round handles
- Zipper closure
- Outer pocket with snap closure
- Inner dividers + zipper closure + card slots
- Detachable shoulder strap
- Faux leather
Style Number/Barcode: 07201-0004
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Expensive Taste Cat Eye Sunglasses
For the bae that likes things to be a little high end, these shades are all you!
- Cat eye design
- Dark lenses
- Thick arm bars
- Gold metal detailing
- 100% UV protection
Style Number/Barcode: 07008-0698
Category Name: Vacation Looks
Price: $5.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Juicy Rainbow Heart Shaped Sunglasses
Keep that style juicy with a pair of rainbow heart shaped sunglasses this summer!
- Rainbow frame
- Heart shape design
- Dark lenses
- 100% UV protection
Style Number/Barcode: 07008-0703
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Day At A Time Quilted Cross-Body Purse
Take it one day at a time with your go-to! We are loving the high end finish of this quilted cross-body! Perfect size for the essentials, and perfect goes-with-everything tonez.
- Medium rectangular structure
- Diamond quilted design
- Double chain handle or Single chain shoulder strap
- Fold over snap closure
- Faux leather
Style Number/Barcode: 07203-0205
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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It's Lit Triangle Swim Top
You'll be lookin' vibrant and bright for all those night swims! Obvi, don't forget to pick up the matching bottoms!- Adjustable Shoulder Straps
- Triangle-Styled Swim Top I Plunging V Neckline
- Removable padding
- Hook & Eye Closure At Back
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0315
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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It's Lit Bikini Bottoms
You'll be lookin' vibrant and bright for all those night swims! Obvi, don't forget to pick up the matching top!
Shop Matching Top: It's Lit Triangle Swim Top
- Adjustable Strappy Sides
- Triangle Front
- Fully lined
- Moderate stretch
- Cheeky Coverage & Fit
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0471
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Break The Rules Strappy One Piece Swimsuit
Get into a little trouble in a bathing suit that makes it easy! Modest in the front, sexy in the back, so you can show them what ur made of!
Fit & Features
- One piece swimsuit
- Straight neckline
- Spaghetti straps that criss cross in the back
- Cheeky bottom | High hips that tie to bottom
- Lavender with a sheen finish
- Moderate stretch | Fully lined
- Removable padding
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0138
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Look Eyelet Knit Skater Dress
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.
Fit & Features
- Eyelet knit fabric with knit lining
- Sleeveless square neckline, underbust seam
- Adjustable spaghetti straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6001
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free