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 Looks
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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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Not Your Babe High-Rise Boyfriend Jeans
You'll be brushing off all the boys when they catch sight of you in these denim boyfriend jeans perfect for flaunting all over town! They feature a flattering high-rise waist, hip-hugging silhouette, relaxed boyfriend style leg, and a clean design on premium light wash denim fabric. Complete the look in a simple corset top.
Fit & Features
- High-rise waist
- Hip-hugging silhouette
- Relaxed boyfriend-style leg
- Front five-button fly closures
- Five-pocket styling, belt loop accents
- Clean premium light wash denim, no stretch
- Runs true to size
Style Number/Barcode: 06602-0425
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty As Can Be Floral Bustier
Create your prettiest outfit yet with this floral bustier perfect for spring activities! It features a strapless curved neckline, flexible boning, side ruched seams, and a curved cropped hem. The bustier top has a floral watercolor print on mesh fabric with a cotton woven lining and no stretch. Complete the look in must-have trouser pants.
Fit & Features
- Strapless curved neckline
- Side ruched seams, flexible boning
- Back zipper and hook-eye closure
- Curved cropped hem
- Floral watercolor print
- Mesh fabric, cotton woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06001-4763
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So In Love Floral A-Line Midi Dress
You'll fall so in love with this floral midi dress to wear for day dates! It features a sleeveless square neckline, elastic ruched straps with lettuce-edge trim, an A-line silhouette, and a flirty front slit. The dress has a dainty rose floral print on stretchy knit-lined fabric. Complete the look in heeled sandals.
Fit & Features
- Sleeveless square neckline
- Elastic ruched straps
- Lettuce-edge trim
- A-line silhouette
- Front slit, midi-length hem
- Dainty rose floral print, stretchy knit-lined fabric
- Runs true to size
Style Number/Barcode: 05102-4921
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Taylor High-Rise Skinny Jeans By Windsor Denim
Curve-flaunting and flattering! The Taylor jeans by Windsor denim show off your best assets and style. They feature a classic high-rise waist, front distressed accents, and on-trend knee cutouts, a skinny-leg design on premium light-wash denim fabric. Style with a flirty satin crop top and heels for a date night.
Fit & Features
- High-rise waist
- Front distressed accents, knee cutouts
- Skinny-leg design
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Light wash denim, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0323
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trip To The Tropics Printed Midi Dress
You'll look like you're ready to whisk away on a tropical vacay in this printed midi dress! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem, a hip-hugging fit and an A-line silhouette, a thigh-high front slit, and an eye-catching tropical palm leaf print. Style with trendy wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, hip-hugging fit, A-line silhouette
- High front slit
- Tropical palm leaf print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4979
Category Name: Vacation Looks
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Remy High-Rise Cuffed Shorts By Windsor Denim
Let your legs out. These jean shorts by Windsor denim hug just right with plenty of stylish deets for flaunting all over social media! Featuring a flattering high-rise waist, front and back distressed accents, a cuffed fray hem, and a form-hugging fit. The shorts are composed of stretchy medium-wash denim with a color fade effect. Complete the look in trendy sandals.
Fit & Features
- High-rise waist
- Front and back distressed accents
- Cuffed fray hem, form-hugging fit
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim, moderate stretch, color fade effect
- Runs true to size
Style Number/Barcode: 06603-0303
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Under The Sun Long Sleeve Tie-Front Crop Top
A crochet crop top perfect for fun under the sun! The top boasts trendy flare long sleeves and a tie-front design that flaunts your figure.
Fit & Features
- Crochet knit fabric
- Flare long sleeves
- Tie-front design
- Ultra cropped hem
- Runs true to size
Style Number/Barcode: 06005-2272
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Remy High-Rise Cut-Off Shorts By Windsor Denim
Your edgy style inspo is here! Introducing your new favorite shorts by Windsor denim that flaunt your cute curves and peeks of skin. They feature a flattering high-rise waist, distressed accents, a cut-off frayed hem, and a vintage-inspired light denim fabric with minimal stretch. Complete the look in a crop top and sandals for the perfect beach day style!
Fit & Features
- High-rise waist
- Distressed accents
- Cut-off frayed hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Light wash denim, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0245
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blooming Beauty Floral Mini Dress
You'll bloom with beauty in this effortlessly stunning floral mini dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with a subtle strappy design, a faux wrap-front silhouette creating an asymmetric mini-length hem, and a curve-hugging fit. The stretchy knit fabric showcases a gorgeous bold floral print. Style with stilettos for a spring date night.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, dual straps, single connecting bar strap
- Faux wrap-front silhouette, asymmetric mini-length hem
- Form-hugging fit
- Bold floral print, knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-1679
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fiercely Stylish Leopard Print Maxi Dress
Keep it fiercely stylish with a maxi dress that brings a chic flair! The lightweight knit dress features a sleeveless V-neckline, spaghetti straps, a maxi-length, flowy, A-line silhouette, a sultry thigh-high front slit, and a trendy leopard print pattern. Complete the look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Maxi-length A-line silhouette
- High front slit
- Leopard print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4968
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's So Trendy Hair Claw Clips
Show off your trendy girl style with these of-the-moment hair claw clips! The pack features three clips, including a rectangular design, a butterfly design, and a flower design. Style these adorable clips with sleek hoop earrings.
Fit & Features
- Three-pack metal claw clip set
- Rectangular design
- Butterfly design
- Flower design
Style Number/Barcode: 07006-0388
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Allure Long Sleeve Lace Mini Dress
Showcase a sweet allure in this beautiful lace mini dress! It features a sweetheart neckline with a lace-up design at the bust, sheer long balloon-style sleeves with cinched hems, ruched detailing down the side and back seams, and a mini-length hem with a curve-hugging silhouette. The partially lined lace fabric features a dainty floral embroidered pattern. Perfect for brides, style with stilettos for your engagement party or bridal shower!
Fit & Features
- Sweetheart neckline, lace-up design at the bust, square back
- Sheer long balloon sleeves, elastic cinched hems
- Ruching down the side and back seams
- Mini-length hem, curve-hugging fit
- Sheer lace fabric, partial knit lining, moderate stretch
- Floral embroidered lace pattern
- Runs true to size
Style Number/Barcode: 05101-2025
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Go Crew Neck Slit Midi Dress
The perfect casual midi dress to look stylish while on the go! It features cap short sleeves, a crew neck, a bodycon silhouette, a side ruched drawstring, and a flirty slit along the hem. The dress is composed of a super soft brushed knit fabric with plenty of stretch. Style with cute slide sandals and a tote bag!
Fit & Features
- Cap short sleeves
- Crew neck
- Bodycon silhouette
- Side ruched drawstring, slit accent
- Midi-length hem
- Soft brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4872
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Charm Tie-Front Midi Dress
Make them all fall for your stylish charm in this adorable midi dress! It features a sleeveless V-neckline with a cute tie-front detail, spaghetti straps, a midi-length hem with a high front slit for a subtle sultry vibe, and a slim-fit silhouette. The lightweight knit fabric has plenty of stretch. Pair with hoop earrings and block heels for a date night.
Fit & Features
- Sleeveless V-neckline, tie-front detail
- Spaghetti straps
- Midi-length hem, high front slit
- Slim-fit silhouette
- Lightweight knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4864
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Irresistible Mesh Midi Dress
You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.
Fit & Features
- Sleeveless plunge v-neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Ruched seams, back slit accent
- Bodycon, midi-length hem
- Mesh fabric, sewn-in knit lining, minimal stretch
- Fits true to size
Style Number/Barcode: 05101-1857
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blooming Beauty Floral Midi Dress
Bloom with beauty in this gorgeous floral midi dress perfect for the season! It features a sleeveless square neckline, spaghetti straps, a knot-front design at the waist with ruching, a midi-length hem with a chic high front slit, and a curve-hugging fit. The stretchy knit fabric showcases a stunning bold floral print. Style with platform heels for a bridal shower.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps, square back
- High waist seam, knot-front design, ruching
- Midi-length hem, high front slit
- Form-hugging fit
- Bold floral print, knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-1678
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Little Bit Of Glamour Rhinestone Bow Sandals
Add a little bit of glamour to your everyday looks with these adorable sandals! They feature a square toe, a clear PVC strap with a sparkling rhinestone bow accent, an open back for easy on-and-off styling, and a flat sole. Style with a chic handbag.
Fit & Features
- Square toe
- Clear PVC strap
- Rhinestone embellished bow accent
- Open back
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1115
Category Name: Vacation Looks
Price: $12.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Dragon Print Tie-Front Top
Layer on this sheer tie-front top to add a trendy vibe to your outfit! It features an open front with a tie-front design that creates a V-neckline, long fitted sleeves, and a cropped, form-hugging fit. The sheer mesh fabric showcases an all-over dragon print for a chic look. Style this top over a basic bodysuit with faux leather pants and clear heels.
Fit & Features
- Open front, tie-front design
- V-neckline
- Long fitted sleeves
- Cropped, form-hugging fit
- Sheer mesh fabric, moderate stretch
- Dragon print
- Runs true to size
Style Number/Barcode: 06202-0249
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Trendsetter Velvet Burnout Corset Top
Showcase a luxe trendsetting look in this elevated-chic corset top! It features a sleeveless sweetheart neckline with padded cups, a ruched draped design at the bust, thin tank shoulder straps with a scalloped trim, a corset-designed bodice with flexible boning, a fitted, cropped hem, and an eye-catching floral velvet burnout pattern on the sheer mesh fabric. Style with dress pants and clear mules.
Fit & Features
- Sleeveless sweetheart neckline, padded cups, ruched draped design at the bust
- Thin tank shoulder straps, scalloped trim, adjustable
- Corset-designed bodice, flexible boning
- Back hook and eye closures
- Fitted, cropped hem
- Floral velvet burnout pattern, sheer mesh fabric, lined bust, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4558
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Country Girl Panama Hat
This trendy panama hat will give you a chic country girl style! It features a structured top, a detailed metal chain-link trim, and a flat, wide brim. Pair with cowboy boots and rhinestone fringe earrings for a music festival!
Fit & Features
- Structured top
- Detailed metal chain-link trim
- Flat, wide brim
- Faux wool material
Style Number/Barcode: 07302-1410
Category Name: Vacation Looks
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny POV Tropical Print Jumpsuit
Get in the sunny state of mind with this tropical printed jumpsuit featuring a deep V-neckline, tie-back halter straps, and a wide-leg silhouette.
Fit & Features
- Knit fabric, high stretch
- Tropical print
- Sleeveless deep V-neckline
- Tie-back halter straps, open back
- High waist seam, ruched sides
- Hip-hugging fit, wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000014
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wanderlust Mode Cutout Tube Top
Shop Matching Pants: Wanderlust Mode Wide-Leg Pants
Fit & Features
- Smooth knit fabrication, double-lined
- Sleeveless square neckline
- Cutout design from bust through hem
- Beaded accents
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06001-000188
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, M, L
Product Badge:- Sale
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Treat Your Feet Foam Bubble Slides
Treat your feet to a low-key massage and walks on a cloud in these foam bubble slides featuring a round toe, wide strap, and comfortable textured foam insoles. Style with a cozy casual jacket for running errands!
Fit & Features
- Round toe
- Wide strap
- Comfort textured foam insole
- Bubble design
- Runs true to size
Style Number/Barcode: 07404-1114
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Date Floral Mini Dress
This romantic floral printed mini dress is perfect for a dinner date at sunset! It features an off-the-shoulder sweetheart neckline, sheer short sleeves, ruched detailing down the side seams, and a short, curve-hugging, bodycon silhouette. Complete the look with strappy heels.
Fit & Features
- Off-the-shoulder sweetheart neckline
- Sheer short fitted sleeves
- Ruching down the side seams
- Mini-length, form-fitting, bodycon silhouette
- Floral print pattern
- Sheer mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1654
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free