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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Keep It On Check Plaid Crop Jacket
Keep your fall look in check in this plaid crop jacket perf for the cozy season! It features long sleeves, a collar neckline, snap-button front closures, flap pockets, and a pull tab hem with button closure. Complete the look in trendy boots.
Fit & Features
- Long sleeves, collar neckline
- Snap-button front closures
- Flap pockets
- Pull tab hem with button closure
- Cropped length
- Plaid pattern, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1421
Category Name: Vacation Looks
Price: $18.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Enticing Flirty Sleeveless Lace-Up Denim Romper
Entice them all with your flirtiness in this denim romper perfect for festivals, concerts, or casual plans! Featuring a square neckline and adjustable thin tank straps, this romper hugs your curves and offers a flirty lace-up front. Perfect for a casual day out, and with a short-length hem, it's the ultimate summer must-have. Complete the look in trendy cowboy boots.
Fit & Features
- Dark wash cotton-blend denim fabric, moderate stretch
- Square neckline
- Adjustable tank straps
- Back zipper with hook and eye closure
- Lace-up
- Form-hugging
- Runs true to size
Style Number/Barcode: 06603-0380
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love For Fall Plaid Cropped Shacket
Showcase your love for this cozy season with this on-trend cropped shacket. It features a collared neckline, long sleeves, a multi-button down front, and a cropped, cinched back hem. The flannel woven fabric features an all-over plaid print, perfect for the fall time. Layer over a bodysuit with faux leather pants for an elevated look.
Fit & Features
- Collared neckline
- Long sleeves, button details
- Multi-button down front
- Buttoned chest pockets
- Cropped hem with a cinched back
- Plaid print, flannel woven fabric
- Runs true to size
Style Number/Barcode: 06204-1450
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Chic Linen Tie-Front Corset Romper
Show up looking casual-chic for your weekend plans in this adorable tie-front corset romper! Designed with a lightweight linen woven fabric, it features a sleeveless square neckline with adjustable spaghetti straps offering a customized fit leading to a back zipper closure. The corset bodice will create that cinched silhouette, followed by a tie-front belt for a cute touch. Style with espadrille wedges.
Fit & Features
- Linen woven fabric
- Square neckline
- Adjustable spaghetti straps, back zipper and hook-eye closure
- Corset bodice, flexible boning
- Tie-front belt, side pockets
- Runs true to size
Style Number/Barcode: 06303-0251
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vibe Of Summer Tie Front Eyelet Crop Top
This gorgeous eyelet crop top will bring you the vibe of summer vacations and parties! The sweetheart neckline flatters your look while the tie front design and spaghetti straps add a playful touch to the cropped hem on breezy eyelet fabric. Complete the look with the matching maxi skirt.
Shop Matching Bottoms: Vibe Of Summer High Rise Eyelet Maxi Skirt
Fit & Features
- Eyelet fabric, moderate stretch
- Spaghetti straps
- Sweetheart neckline
- Tie front
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5358
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Like Me Cutout Wide-Leg Jumpsuit
Make a striking impression in this bold strapless jumpsuit on vacay or a summer night out! With O-ring inserts, a cutout bodice, and a flattering wide-leg fit, this jumpsuit will turn heads everywhere you go.
Fit & Features
- Smooth knit stretchy fabric, full knit lining
- Strapless neckline
- O-ring inserts, cutout bodice
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000036
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Festival Vibes Halter Crop Top
Showcase trendy festival vibes all season with this alluring crop top! It features a sleeveless halter neckline with spaghetti straps in a cross-front design and a cropped, form-hugging fit. Style with the matching wide-leg pants and retro shades.
Shop Matching Bottoms: Festival Vibes Wide-Leg Pants
Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, cross-front design, tie at the back of the neck
- Cropped, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06001-4029
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Minimalistic Chic Faux Leather Belt
Add the perfect touch of chic to your look with this faux leather belt featuring a sleek metal buckle accent, dual bands with perforated holes, and a pull-through design. Complete the look in a form-fitting jumpsuit and heels.
Fit & Features
- Sleek metal buckle accent
- Dual faux leather bands
- Perforated holes
- Pull-through design
Style Number/Barcode: 07301-0468
Category Name: Vacation Looks
Price: $3.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stay Forever Chic Faux Wool Hat
You'll stay forever chic with this of-the-moment faux wool hat! It features a structured top with a wide flat brim and a sleek faux leather trim. Style with a mock neck bodysuit and your fave pair of denim.
Fit & Features
- Structured top
- Wide flat brim
- Thin faux leather trim, adjustable buckle detail
- Faux wool material
Style Number/Barcode: 07302-1394
Category Name: Vacation Looks
Price: $7.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty Fun V-Neck Tie Striped Knit Crop Top
Give your vacay style a dynamic upgrade in this flirty knit crop top perfect for a getaway or weekend fun! The top boasts a sultry V-neckline, dual tie-back design, and an ultra-cropped hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching skirt.
Shop Matching Skirt: Flirty Fun High Rise Striped Knit Midi Skirt
Fit & Features
- Pointelle knit fabric, striped pattern
- V-Neck
- Dual tie-back design
- Ultra-cropped length hem
- Runs true to size
Style Number/Barcode: 06005-1970
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutie In A Lug Bootie
Hey, there cutie rocking these lug sole booties! They feature a round toe, chunky block heel, and rib-knit upper design on faux leather material. Complete the look in a flannel shacket for cold-weather vibes.
Fit & Features
- Almond toe
- Lug sole
- Chunky block heel
- Rib-knit upper design
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1584
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Vibe Tie-Back Flowy Floral Woven Maxi Dress
Give off a charming vibe at summer parties in this simply stunning floral woven maxi dress! The breezy lightweight woven fabric is detailed with a gorgeous floral print pattern and includes a mini-length lining for coverage. The sleeveless bodice is shaped with a sweetheart neckline, a dainty tie-front bust design for a cute detail, and spaghetti straps leading to an open back with a cross-back strappy design and a customized tie closure. The fitted high waist flows out to a maxi-length hem with an effortlessly chic A-line silhouette. Style with hoop earrings and slip-on sandals.
Fit & Features
- Floral print
- Lightweight woven fabric, mini-length woven lining, no stretch
- Sweetheart neckline with tie-front bust, spaghetti straps
- Open back, cross-back strappy design, tie closure
- High waist seam
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3048
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Search Of Luxe Gold Leaf Trim Hat
Your search for luxe ends here with this faux wool hat! It features a stunning gold leaf trim on a thin faux leather band and a wide brim. Complete the look in a polished plaid blazer.
Fit & Features
- Gold leaf trim, thin faux leather band
- Wide brim
- Faux wool material
Style Number/Barcode: 07302-1396
Category Name: Vacation Looks
Price: $5.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charmed By You Sleeveless Lace Crop Top
Charm them all with your adorable flair in this sleeveless lace crop top! Made of soft knit floral lace fabric, it's both stylish and comfortable. It features a square neckline, bungee spaghetti straps, and a ruched bust for a flattering fit. Complete your look with light-wash jeans and sneakers.
Fit & Features
- Floral lace knit fabric, sewn-in lining, moderate stretch
- Bungee spaghetti straps
- Square neckline
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5184
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kiss the Spotlight Halter Romper
Flirty, flowy, and low-key iconic. This romper’s deep neckline and twirl-worthy shorts bring main feed energy to your night-out lineup.
Fit & Features
- Slinky knit stretchy fabric
- Halter plunge neckline, tie straps
- Open back
- Flowy shorts hem
- Runs true to size
Style Number/Barcode: 06503-000079
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wear Your Art Striped Midi Dress
Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!
Fit & Features
- Long sleeves
- Front and back v-necklines
- Bodycon silhouette
- Tie-front waist
- Midi-length hem
- Marble striped print, stretch-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4821
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet One Off-The-Shoulder Crop Top
Show off your sweet side in this off-the-shoulder crop top perfect for summer fun! Features a sweetheart neckline and short sleeve cuffs for a flattering fit. The adjustable drawstring allows for a customizable look and the cropped hem adds a touch of trendiness. Complete the look in denim shorts and sandals for a day out!
Fit & Features
- Stretchy rib knit fabric
- Off-the-shoulder, sweetheart neckline
- Adjustable drawstring
- Cropped length
- Runs true to size
Style Number/Barcode: 06002-1865
Category Name: Vacation Looks
Price: $22.90
Availability: Out of Stock
Product Badge:- Ships Free
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Next Level Faux Suede Mini Skirt
Take your look to the next level with a mini skirt that slays! The skirt features a high-rise waist, a lattice tie-up front, and a mini-length hem. The skirt is composed of a lined faux suede fabric that offers a form-hugging fit with slight stretch. Complete look with a crop top and wedges.
Fit & Features
- High-rise waist
- Back zipper closure
- Lattice-tie front
- Mini-length hem
- Lined faux suede fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0457
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetly Femme Floral Corset Lace-Up Mini Dress
Sure to be a staple in your rotation, this super sweet floral mini dress is designed with a corset bodice and lace-up back that accentuates your femme figure along the A-line silhouette.
Fit & Features
- Floral print, chiffon-lined fabric
- Sweetheart neckline, bust tie, underwire bust
- Wide shoulder straps, side zipper and hook-eye clsoure
- Corset bodice, lace-up back
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4054
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Pretty Chiffon Midi Dress
Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.
Fit & Features
- Sweetheart neckline, ruched bodice
- Long sheer peasant sleeves, elastic cinched hems
- Stretchy smocked back design
- Fitted high waist seam
- Midi-length hem, high front slit, A-line silhouette
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4954
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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90s Classic Patchwork Denim Bucket Hat
Experience the nostalgia of the 90s with this trendy patchwork denim bucket hat! It features a classic patchwork design on denim material and has adjustable inner strings to get the perfect fit. Complete the look in a denim mini dress!
Fit & Features
- Patchwork design, denim material
- Adjustable inner strings
- Bucket hat style
Style Number/Barcode: 07302-1614
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wanting More Strapless Lace Knit Maxi Dress
Leave everyone wanting more when you're in this lace knit maxi dress! Perfect for any summer plans, this dress flaunts a sleek strapless neckline and form-hugging fit that flares out into a long hem.
Fit & Features
- Lace knit fabric, lined
- Strapless neckline
- Form-hugging fit
- Flared maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000057
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seal The Deal Trouser Joggers
These casual and chic trouser joggers will have you business ready to take on the day! They feature a high-rise waist, pintuck pleated detailing, dual front pockets, a relaxed fit, and a trendy jogger hem. The lightweight woven fabric has no stretch. Style these pants with a bodysuit and a structured blazer.
Fit & Features
- High-rise waist, belt loops
- Hidden front zipper, hook and bar, and button closure
- Pintuck pleated detailing
- Dual front pockets
- Relaxed fit, elasticized jogger hem
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-1280
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wanderlust Calling Strapless Abstract Flowy Tunic Top
Breeze into the sunny season in this strapless tunic top with a pretty abstract print on a flowy long silhouette and a flirty center slit design. Style as a cover-up or by itself on vacation, at festivals, or a beach day!
Fit & Features
- Abstract print, sheer chiffon fabric
- Strapless neckline with metal insert, bust lining
- Center slit design
- Flowy long silhouette
- Runs true to size
Style Number/Barcode: 06003-2751
Category Name: Vacation Looks
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free