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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Frayed Fashionista Jean Mini Skirt
Show 'em who's the real fashionista in this frayed jean mini skirt! It features a high rise waist, the traditional five pocket and belt loop design, a front button down closure, seam detailing, and a raw, frayed hem. The medium wash skirt is composed of a denim fabric with no stretch.Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06601-0162
Category Name: Vacation Looks
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Fab Distressed Jean Mini Skirt
Yes girl, you'll look so fab in this distressed jean mini skirt! It features a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, distressed detailing, a frayed hem, and an overall faded look. The medium wash jean skirt is composed of a denim fabric that offers moderate stretch and a form-fitting style.Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06601-0158
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Laced Up Mini Skirt
Get all laced up in this trendy and fun white mini skirt! It features a high rise waist, the traditional five pocket and belt loop design, a front button and zipper closure, lattice accents along the sides, a frayed hem, and a form hugging fit. The skirt is composed of a denim fabric with moderate stretch.
Style Number/Barcode: 06601-0000
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Reign In Floral Romper
Reign like the stunning queen you are in flirty floral with this adorable romper! It features a sleeveless bodice, spaghetti straps, a V neckline, a faux wrap front with a flowy overlay and faux tie detail, and fitted shorts. The black romper showcases a pretty ditsy floral print. and is composed of a stretchy knit fabric.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06503-0948
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Passport To Paradise Romper
Transport yourself to paradise with this vacay-ready romper! It features a white hued floral lace bodice with a plunging V neckline, adjustable narrow straps and a sheer unlined back. The shorts feature a vibrant red hue with cinching tie waist accent, wide leg opening and a yellow floral print. Romper is composed of a combination lace and crepe fabric that offers a form hugging fit with minimal stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06503-0933
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Clearance
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Elevated Era Ribbed Knit High Slit Midi Skirt
Enter your elevated era with this chic staple ribbed knit midi skirt perf for everyday styling. Designed with a high-cut side slit and bodycon fit, pair with the matching cropped tank for a seamless look.
Shop Matching Top: Elevated Era Ribbed Knit Cropped Tank Top
Fit & Features
- Ribbed knit fabric, high stretch
- High-rise waist
- High side slit
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1135
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crochet All Day Romper
Crochet all day in this fresh and fun romper! It features a sleeveless bodice, adjustable spaghetti straps, a plunging V neckline, padded cups, a crochet detailed top, a high waist seam, a back zipper closure, and fitted shorts. The ivory romper is composed of a crepe fabric that offers a form-fitting style.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06503-0922
Category Name: Vacation Looks
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sprung On Florals Jumpsuit
These pretty floral prints have got us sprung! Let this jumpsuit charm with it's straight strapless neckline, hidden side pockets and flared wide leg pants. Jumpsuit is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06502-2199
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stand Out In Stripes Shorts
Stand out in trendy stripes in these cute black shorts! They feature a high rise waist, a cinching tie waist belt and a wide leg bottom opening. The all over white contrasting stripes are complemented with a black background for a classic vibe! Shorts are composed of a stretchy knit fabric that offers a form hugging fit. Be sure to pick up the matching top to complete your look!Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06503-0008
Category Name: Vacation Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fresh For Spring Romper
Have a totally fresh for spring look with this adorable floral romper! It features a sleeveless bodice, spaghetti straps, a plunging V neckline and back, a high waistband, loose fitting shorts, and a pretty all over print with hues of pink, yellow, and gray. The romper is composed of a knit fabric with moderate stretch.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 06503-0007
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go Getter Striped Jumpsuit
You're a go-getter, so dress the part! This boss babe jumpsuit features a solid white bodice with an off the shoulder neckline, short sleeves, and a hidden back zipper closure. Black and white striped pants have a high waist seam and wide pant legs.Model is 5'8" with a 32" bust, 23" waist, and 36" hips. She is wearing a size small
Style Number/Barcode: 06502-2179
Category Name: Vacation Looks
Price: $4.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Vibes Wide Leg Pants
Get all those vacay on a tropical island vibes with these wide leg pants! They feature a high rise elastic banded waist paired with wide pant legs with a flared hem. The black bottoms are composed of a stretchy knit fabric and showcase a fun all over leaf print with beige hues. Complete your vacation ready look with the matching tube top!Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06502-2097
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stand Out Striped Tie Front Jumpsuit
Be sure to stand out with this super chic black and white dash-striped jumpsuit! It features a deep V neckline with a keyhole tie front, spaghetti straps, and long wide pants. Jumpsuit is composed of a knit fabric with plenty of stretch.Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06502-0050
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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One Knit Wonder Jumpsuit
This jumpsuit is serving up stylish statement looks! It features two wide convertible straps that can be used to create all your favorite necklines and unique designs. The pants feature an elongating wide leg pant that brings plenty of flair! Jumpsuit is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06502-0009
Category Name: Vacation Looks
Price: $42.90
Availability: Out of Stock
Product Badge:- Clearance
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Such A Charmer Mini Skirt
Charm them all with style with this sultry mini skirt! It features a high rise waist, a front twist accent, and a short, fitted look. The snake printed skirt is composed of a lightweight knit fabric that offers plenty of stretch and a form hugging fit. Don't forget to purchase the matching crop top!
Style Number/Barcode: 06501-3023
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bright And Early Midi Skirt
Start bright and early with a little hot neon 'fit! The asymmetrical skirt has a high waist paired with a knot hip detail and a high slit. The skirt has a form fitting fabric composed of a smooth knit that offers a moderate stretch. Don't forget to purchase the matching top.Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06501-3067
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pleat Me Right High Waist Mini Skirt
Dress up in a pleated mini skirt! Step out for a night out in a high waist mini skirt that features a tulip-hem with subtle mini pleats and is composed of a crepe knit fabric that offers a form hugging fit. Complete your look with a basic knit top for a minimal vibe and hoop earrings.
Fits & Features
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High rise waist
- Tulip hemline with mini pleats
- Crepe knit composition
- Moderate stretch for a comfy fit
Style Number/Barcode: 06501-2782
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High rise waist
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Glow With Me Skater Romper
Glow and make a vibrant entrance in this orange skater romper! This flowy, dressy piece features a deep V neckline with a wrap bodice that ties at the waist, a fold over collar, a hidden side zipper closure, and shorts with a skirt overlay for a skater dress effect. Romper is composed of a chiffon fabric with no stretch.Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 06403-1050
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fab And Fresh Maxi Skirt
You'll be feelin' so fab and fresh in this hot maxi skirt! It features a high rise elastic banded waist, side ruched detailing, and an asymmetrical hem. Skirt is composed of a stretchy knit fabric that offers a form hugging fit and includes a short knit lining. Complete your look with the matching crop top!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06501-0020
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Gives You Lemons Pajama Shorts
When life gives you these lemon pajama shorts every lounge or sleep will look sweet! Pair with the matching pajama top to complete the look.
Fit & Features
- Lemon print, stretchy knit fabric
- Mid-rise waist
- Form-hugging fit
- Cheeky bottom
- Runs true to size
Shop The Matching Pajama Top: Gives You Lemons Pajama Top
Style Number/Barcode: 07103-000017
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready To Ruffle Maxi Skirt
You'll be ready to ruffle in this flirty mauve maxi skirt! It features a high rise waist, a major front slit with ruffle details, and a long maxi length with a relaxed fit. The skirt is composed of a crepe fabric with moderate stretch.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 06501-0004
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Clearance
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High Slit Snake Maxi Skirt
Raise the stakes in snake print! This bold skirt features a high rise waist and a maxi length silhouette with a high side slit. Skirt is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch.
Style Number/Barcode: 06501-0007
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Clearance
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Picnic Time Gingham Paper Bag Shorts
Spend a gorgeous summer day outdoors in these red gingham paper bag shorts! They feature a high paper bag waist with a tie belt, slanted front pockets, a hidden back zipper and hook and eye closure, and a relaxed fit throughout. Shorts are composed of a woven fabric with an all over gingham print. Pair with matching crop top to complete the set!Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 06403-1027
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On The Rise Shorts
Elevate your look in these statement making shorts! They feature a a high rise waist, vertical seams and a slim, tapered fit. Includes a hidden back zipper. Shorts are composed of a thick knit fabric with a knit lining.
Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06403-1046
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance