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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Taylor High-Rise Destructed Skinny Ankle Jeans by Windsor Denim
This pair of Taylor skinny ankle jeans by Windsor Denim will instantly become a new fave! They feature a high-rise waist, light-destructed detailing down the front, a skinny-leg fit, and an ankle-cut hem. The dark wash denim fabric features minimal stretch and color fading for the perfect vintage look. Style with a crop top and booties.
Fit & Features
- High-rise waist
- Light-destructed detailing down the front
- Skinny-leg fit, ankle-cut hem
- Five-pocket and belt loop design
- Front button and hidden zipper closure
- Dark wash denim fabric, minimal stretch, color fading
- Runs true to size
Style Number/Barcode: 06602-0379
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Appearance Side-Tie Wrap Denim Skort
Your summer style wouldn't be the same without this mini denim skort to make stylish appearances! This form-hugging, high-waisted denim skort boasts a stylish faux wrap skirt overlay with a side tie, adding both function and flair to your wardrobe. The frayed hem adds a touch of edginess. Complete the look in a basic top.
Fit & Features
- Dark wash denim, slight stretch
- High-rise waist, front zipper closure
- Faux wrap skirt overlay, side-tie
- Form-hugging fit
- Frayed short hem
- Runs true to size
Style Number/Barcode: 06603-0390
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Delicate Blooms Flower Hair Clips
Tame your tresses while giving your hair a luxe look! This hair clip set features a flower design with rhinestone embellished petals, a faux pearl center, and a sleek metal frame. Style with sleek hoop earrings to complete the look!
Fit & Features
- Hair clip set
- Flower design
- Rhinestone embellished petals
- Faux pearl center
- Sleek metal frame
Style Number/Barcode: 07006-0377
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Factor Snake Chain Panama Hat
Amp up the chic factor of your look with this trendy panama hat! It features a structured top with a wide flat brim and a sleek snake chain trim. Style with hoop earrings.
Fit & Features
- Panama hat design
- Structured top
- Wide flat brim
- Thin snake chain trim
- Faux wool material
Style Number/Barcode: 07302-1393
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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See My Style Clear Box Handbag
Show everyone your new favorite handbag! It features a clear box-shape design, a rhinestone handle, push-lock closure, and a detachable chain link strap. Complete the look in rhinestone heels for a social occasion!
Fit & Features
- Clear box-shape design
- Top push-lock closure
- Rhinestone handle
- Spacious interior
- Detachable chain link strap
Style Number/Barcode: 07204-0678
Category Name: Vacation Looks
Price: $14.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dazed And Chic Hoop Earrings Set
Everyone will be in a daze at you in these chic hoop earrings! The set features three pairs of assorted shapes and sizes with a multi-layered design, sleek twist, and textured metal frames and each with omega-back closures. Style with a posh cardigan to complete your trendy look!
Fit & Features
- Three pair earrings set
- Assorted shapes and sizes
- Sleek twist and textured metal frames
- Multi-layered design
- Each with omega-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1423
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Deets Duster Earrings
You'll absolutely adore the dainty details of these duster earrings! They feature a linear design with a thin chain and small round accents. Style with a trendy ring set.
Fit & Features
- Linear design
- Thin chain
- Small round accents
- Post-back closure
- Metal material
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1434
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fab And Trendy Rhinestone Low Heel Mules
These fab and trendy rhinestone mules will amp up your looks! They feature an open square-shaped toe, a wide banded strap with all-over mini rhinestone embellishments, a slide-on design with an open back, and a low block heel. Style with sleek hoop earrings.
Fit & Features
- Open square-shaped toe
- Wide banded strap, mini rhinestones
- Slide-on design, open back
- Low block heel
- Satin woven fabric, faux leather insole
- Runs true to size
Style Number/Barcode: 07404-1096
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Babe Ribbed Knit Flare Pants
Style up these comfy ribbed knit flare pants and you'll be a total trendy babe! They feature a high-rise elasticized waist, a hip-hugging fit that continues down the leg, and a flared-out hem. The ribbed knit fabric offers plenty of stretch for comfortable wear. Pair with a crop top and a button-down shacket for the cutest look!
Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flared-out hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-2262
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Downtown Girl Faux Wool Cabby Hat
You'll need this cabby hat as you make your way downtown! It features a wide brim, classic cabby-hat styling, and is made of faux wool material. Complete the look in a trendy denim jacket.
Fit & Features
- Wide brim
- Classic cabby-hat styling
- Faux wool material, woven lining
Style Number/Barcode: 07302-1395
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Run This Town Platform Caged Heels
You'll run this town in elevated fashion! These chunky heels feature a square toe, caged toe straps, a platform sole, a block heel, and an adjustable ankle strap with buckle closure on faux leather material. Layer a fab faux fur jacket to complete your style slay!
Fit & Features
- Square toe
- Caged toe straps
- Platform sole
- Block heel
- Adjustable ankle strap with buckle closure
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4160
Category Name: Vacation Looks
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Chic Houndstooth Woven Shacket
This elevated chic houndstooth woven shacket will step up your everyday winter outfits! It features a collared neckline, long sleeves, a complete button-down front, a relaxed fit, and an all-over trendy houndstooth pattern on the woven fabric. Layer this cute shacket over a bodysuit with faux leather leggings.
Fit & Features
- Collared neckline
- Long sleeves
- Button-down front
- Chest flap pockets
- Relaxed fit
- Houndstooth pattern, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1513
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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To The Point Faux Leather Booties
These faux leather booties are essential for dressing up or down! They feature sleek pointed-toe, block-heel, and side knit panels for easy pull-on/off styling. Complete the look in a polished trench coat.
Fit & Features
- Pointed-toe
- Block heel
- Side knit panels
- Easy pull-on/off styling
- Faux leather material
Style Number/Barcode: 07403-1634
Category Name: Vacation Looks
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Strike Em' In Rhinestone Cowboy Hat
Strike 'em' with a glamorous look in this cowboy hat featuring a classic curved brim, and rhinestone trim, and it is composed of faux wool material—style with a casual jacket to complete the look.
Fit & Features
- Classic curved brim
- Rhinestone trim
- Cowboy design
- Faux wool material
Style Number/Barcode: 07302-1417
Category Name: Vacation Looks
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Style So Sleek Faux Leather Puffer Vest
Your style will be looking so sleek layering on this faux leather puffer vest to elevate your outfit! The sleeveless vest features a standing collar neckline, front zipper and snap-button closures, hidden side pockets, and a fitted hem. The vest is composed of an insulated woven fabric designed to help keep you cozy and protected from the elements! Complete the look in casual cargo joggers.
Fit & Features
- Sleeveless, standing collar neckline
- Front zipper and snap-button closures
- Hidden side pockets
- Fitted hem
- Insulated faux leather lined fabric
- Fits true to size
Style Number/Barcode: 06201-0326
Category Name: Vacation Looks
Price: $17.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Strut It Out Abstract Zebra Tie-Front Top
Fit & Features
- Sheer mesh fabrication
- V-neckline
- Tie-front bodice
- Long sleeves
- Zebra print
- Cropped hem
- Runs true to size
Shop Matching Skirt: Strut It Out Abstract Zebra Maxi SkirtStyle Number/Barcode: 06202-0505
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Go With The Flow Floral Midi Dress
You'll love the casual vibes of this breezy floral midi dress! It features a sleeveless V-neckline with a padded bust and a draped accent, side cutouts at the waist, adjustable spaghetti straps that lead to a cross-back design, a partially open back with an elastic band, a flowy, midi-length, A-line silhouette, and a high front slit. The lightweight woven fabric features an all-over dainty floral print pattern. Style this dress with hoop earrings.
Fit & Features
- Sleeveless V-neckline, padded bust, draped accent
- Side cutouts at the waist
- Adjustable spaghetti straps, cross-back design
- Partially open back, elastic band, zipper, hook and eye closure
- Flowy, midi-length, A-line silhouette, front slit
- Floral print, woven fabric, lining at the bust, no stretch
- Runs true to size
Style Number/Barcode: 05101-2313
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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My Edgy Side One Shoulder Bodysuit
Turn up your stylish edge in this sleek and chic faux leather bodysuit featuring a one-shoulder crew neckline, a fitted long sleeve, a back keyhole with button closure, and a sultry waist cutout. Style with straight-leg jeans to complete the look!
Fit & Features
- One-shoulder crew neckline
- Fitted long sleeve
- Back keyhole with button closure
- Waist cutout accent
- Faux leather fabric
- Fits true to size
Style Number/Barcode: 06001-4383
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Best Match Plaid Slit Mini Skirt
From cool mornings to chilly afternoons, look stylish no matter the weather in this plaid mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look in the matching shacket and knee-high boots.
Shop The Matching Shacket: Best Match Plaid Longline Shacket
Fit & Features
- High-rise waist
- Back zipper closure
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Plaid pattern, soft woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06401-0462
Category Name: Vacation Looks
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Best Match Plaid Longline Shacket
From cool mornings to chilly afternoons, look stylish no matter the weather in this plaid mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look in the matching cozy skirt and knee-high boots.
Shop Matching Bottoms: Best Match Plaid Slit Mini Skirt
Fit & Features
- Long sleeves, button cuffs
- Collar neckline
- Front button-down closures
- Flap pockets, side slit accents
- Longline hem
- Plaid pattern, soft woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1459
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Layered In Luxe Faux Leather Trench Coat
You'll be layered in luxe in this trendy faux leather trench coat! It features a faux fur lapel collar, long sleeves with a faux fur trim, dual button-front closures, a belted waist to stylishly cinch your silhouette, and a long-line hem. The smooth faux leather fabric includes a woven lining. Pair over a crop top and a satin midi skirt with knee-high boots for a city-chic look.
Fit & Features
- Faux fur lapel collar
- Long sleeves, faux fur trim
- Dual button-front closures
- Belted waist, rectangular buckle, lined side pockets
- Long-line hem
- Faux leather fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06204-1503
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Glamour Gemstone Ring Set
Bring bold glamorous vibes to your everyday look with this trendy ring set! The pack features five sleek metal bands with varying designs with gemstone and rhinestone embellishments. Style this set with a dainty choker necklace.
Fit & Features
- Five-pack ring set
- Gemstone and rhinestone embellishments
Style Number/Barcode: 07004-0308
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Central Park Chic Trench Coat
Layer on this structured trench coat for a city-chic look! Featuring a lapel collar, long sleeves, hidden lined side pockets, and a long-length hem, this fleece coat is a perfect pick for the season. Style over a mock neck bodysuit with dark wash denim.
Fit & Features
- Lapel collar
- Long sleeves
- Dual hidden side pockets, smooth woven lining
- Long-length hem, fitted silhouette
- Fleece fabric, little to no stretch
- Runs true to size
Style Number/Barcode: 06201-0330
Category Name: Vacation Looks
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Style Zebra Print Midi Skirt
Show off a trendy wild style in this eye-catching zebra print midi skirt! It features a high-rise waist, a midi-length hem with a sultry thigh-high side slit, and a hip-hugging fit flowing out to an A-line silhouette. The skirt is composed of a knit fabric with a moderate stretch. Style with a basic bodysuit and ankle booties.
Fit & Features
- High-rise waist
- Midi-length hem
- High side slit
- Form-hugging fit throughout the hips
- A-line silhouette
- Zebra print pattern, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0798
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance