Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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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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Romance Era Floral Brocade Corset Mini Dress
You'll be in your romance era in this chic floral brocade corset mini dress! Designed with a detailed floral brocade woven fabric with a knit lining, this dress will bring the allure to your date night look. The top is shaped with a sleeveless sweetheart neckline with a padded bust and structured underwire to provide support and eliminate the need for a bra. The corset-style bodice has flexible boning to create that sultry snatched silhouette. Find your perfect fit with the adjustable spaghetti straps that lead to a back zipper closure. The form-hugging silhouette on the mini-length dress will flaunt your stunning curves. Complete your 'fit with stilettos.
Fit & Features
- Floral brocade woven fabric with knit lining, minimal stretch
- Sleeveless sweetheart neckline with structured and padded bust
- Corset bodice with flexible boning, high waist seam
- Adjustable spaghetti straps, back zipper with hook and eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-3177
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Flutter Butterfly Hair Clip Set
Make hearts flutter when you style up your pretty tresses with this butterfly hair clip set! The pack of two dainty clips features a beautifully detailed butterfly design made from a sleek gold metal material. Complete the look with hoop earrings and a charm necklace.
Fit & Features
- Two-pack hair clip set
- Detailed butterfly design
- Gold metal material
Style Number/Barcode: 07006-0458
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Flair Ruffled Wrap Chiffon Mini Dress
This adorable floral chiffon mini dress will bring the flirty flair to your spring parties! Designed with a dainty floral print on lightweight lined chiffon fabric. This mini-length dress features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps that lead to an open back with a cross-back strappy design, and a corset-style bodice with a fitted high waist. The A-line silhouette has a faux wrap-front creating the cutest asymmetric ruffled hem. Complete your look with strappy sandals.
Fit & Features
- Sheer chiffon fabric with knit lining, minimal stretch, dainty floral print
- Sleeveless sweetheart neckline, padded bust
- Spaghetti straps
- Open back, cross-back straps with tie closure, lower zipper, hook and eye closure
- Corset bodice, high waist seam
- Faux wrap-front, asymmetric ruffled hem, A-line fit
- Runs true to size
Style Number/Barcode: 05101-3113
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorably Chic Bow-Detailed Ruffled Mesh Mini Dress
This bow-detailed ruffled mesh mini dress is so adorably chic and perfect for date nights or parties! Made with an airy sheer mesh fabric with a full-length knit lining, this dress gives those effortless breezy vibes. The sleeveless square neckline shapes the bodice, and the adjustable spaghetti straps offer a customized fit. The dress features a ruffled tiered silhouette for the cutest look, detailed with dainty bow accents. The tiers have elastic seams for stretch. The flowy A-line fit on the mini-length hem will give your 'fit a feminine touch. Style with lace-up heels.
Fit & Features
- Non-stretch sheer mesh fabric, stretchy knit lining
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruffled tiered silhouette with bow accents
- Elastic seams for stretch
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5618
Category Name: Vacation Looks
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paisley Babe Cowl Neck Slit Maxi Dress
Get ready to turn heads in this paisley maxi dress! This sleeveless dress features a flirty cowl neckline, delicate spaghetti straps, and a flowy silhouette that's perfect for a day out or a backyard dinner party. With a high front slit and stunning paisley print, this maxi dress is sure to become a staple in your wardrobe. Complete the look in flat sandals.
Fit & Features
- Paisley print, stretchy knit fabric
- Spaghetti straps
- High front slit
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-5513
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Vacation Looks
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless And Fab Rhinestone Strappy Flat Sandals
These faux leather flat sandals are your ticket for looking effortless and fab out with friends! Designed with a chic square toe and a mix of rhinestone embellished and plain straps, these sandals will add a touch of glamour to any outfit. Plus, their easy slip-on-and-off design makes them perfect for switching out heels or styling on the go. Complete the look with a cute handbag.
Fit & Features
- Flat sole
- Slip-on
- Strappy design
- Square toe
- Luxe fit cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1151
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Factor Ruched Velvet Burnout Mini Dress
Level up the luxe factor of your going-out look with this chic velvet burnout mini dress! The lined mesh fabric is accented with an intricate velvet burnout scroll pattern for that eye-catching vibe. The mini-length dress features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams to accentuate your curves, and a bodycon silhouette. Style with lace-up stilettos!
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Velvet burnout scroll pattern
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5521
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ever So Charmed Puff Sleeve Floral Babydoll Dress
Everyone will be charmed by you in this adorable floral babydoll dress at parties and afternoon soirees! Crafted from an airy woven fabric showcasing a floral embroidered pattern, this short dress will be your staple for spring to summer. Features trendy puff short sleeves, a flattering square neckline, and a babydoll silhouette with a short-length hem. Complete the look with heeled sandals and a fab ring set.
Fit & Features
- Airy woven fabric lined with woven fabric
- Floral embroidered pattern
- Stretchy smocked back, zipper and hook-eye closure
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05101-3358
Category Name: Vacation Looks
Price: $10.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset View Satin Abstract Mesh Corset Top
The perfect abstract satin corset top for dinner with a sunset view! Featuring a sweetheart neckline, adjustable spaghetti straps, and molded cups for support. The sheer mesh bodice offers a snatched look with flexible boning inserts while the cropped hem flaunts your figure and multiple back hook and eye fasteners allow for a customizable fit. Complete the look in form-hugging shorts for a sexy style!
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Built-in padded underwire bust
- Sheer mesh bodice, flexible boning, cropped hem
- Multiple back hook and eye fasteners
- Abstract print, satin fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06001-5015
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Rhinestone Criss-Cross Strap Faux Leather Sandals
Amp up your warm-weather 'fits with these glam rhinestone strappy sandals! Made with a smooth faux leather material, these sandals feature a square-shaped toe with a curved criss-cross strap design accented with mini rhinestone embellishments for that chic sparkle. The slip-on-and-off design on the flat sole allows for effortless styling, and the lightly padded insole provides comfortable wear. Pair these sandals with hoop earrings.
Fit & Features
- Flat sole
- Faux leather upper
- Square toe
- Curved criss-cross strap design, mini rhinestones
- Slip-on-and-off styling
- Lightly padded insole
- Runs true to size
Style Number/Barcode: 07404-1173
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Chic Espadrille Wedges
Take a chic stroll in this espadrille wedges on a sunny day perfect for giving every outfit a fresh lift! From beach days to pool parties, and vacay, these wedge sandals are a must to have in your lineup. Designed with an almond toe, a wide strap for comfort and support, and an elevated wedge heel with a rubber sole. Complete the look with a jelly handbag to keep your essentials in!
Fit & Features
- 4" Wedge heel
- Slip-on
- Almond toe
- Faux leather footbed, rubber sole
- Espadrille material
Style Number/Barcode: 07406-0349
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Bound Tropical Print Woven Maxi Dress
Jet set to your gorgeous getaway in this tropical woven maxi dress! The lightweight gauze woven fabric features a bold tropical print to bring the allure to your dreamy vacay. The maxi-length dress is shaped with a strapless straight-across neckline with a ruffled fold-over design to add a flirty flair. The fitted high waist seam has an elasticized design for added stretch and a thin tie-front belt with cute tassel accents. The dress flows out to a floor-length hem with an effortless A-line silhouette. Style this maxi dress with strappy sandals.
Fit & Features
- Tropical printed gauze woven fabric with short knit lining, minimal stretch
- Strapless straight neckline with no-slip strip, ruffled fold-over design
- Fitted elasticized high waist seam
- Tie-front belt with tassels
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5678
Category Name: Vacation Looks
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adoring Looks Puff Sleeve Lace-Up Peplum Crop Top
Catch many adoring looks in this peplum crop top perfect for your upcoming weekend plans! With a flattering elasticized square neckline, adorable short puff sleeves, and a peplum hem, this crop top is both flirty and cute. The lace-up back adds a touch of unique flair to the woven fabric. Style this crop top with a denim mini skirt and sandals.
Fit & Features
- Woven fabric, no stretch
- Lace-up
- Peplum crop hem
- Runs true to size
Style Number/Barcode: 06003-2443
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeten Me Up Square Neck Cutout A-Line Midi Dress
Sweeten your style in this breezy A-line midi dress perfect for bridal showers, day dates, or brunch! With a sleeveless square neckline and adjustable spaghetti straps, this cotton midi dress offers a flattering fit while the stretchy smocked bust with lace-up detail adds a touch of sweetness. The cutout back with elasticized straps adds a hint of daring to the fitted bodice and A-line silhouette. Complete the look in strappy sandals for a chic allure.
Fit & Features
- Lightweight cotton woven fabric with lining
- Adjustable spaghetti straps
- Smocked lace-up bust
- Cutout back
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5611
Category Name: Vacation Looks
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clearly Adorable Tote Bag And Pouch
So adorable, this clear tote bag and pouch will be the cutest addition to your closet! The large clear PVC tote is accented with a sleek faux leather trim, faux leather shoulder straps, and an attached faux leather pouch to keep all of your essentials on hand. Style this trendy tote with rhinestone stud earrings.
Fit & Features
- Large clear PVC tote design
- Faux leather trim
- Dual faux leather shoulder straps
- Faux leather zipper pouch
- Lobster clasp detail
Style Number/Barcode: 07203-1934
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Up Gemstone Strap Jelly Sandals
Glam up your look for spring and summer with these fab gemstone strap jelly sandals! Made from a trendy jelly material, these sandals feature a round toe, a mini rhinestone-embellished trim, and a thin thong strap design accented with iridescent gemstones and rhinestones for that gorg sparkle. The slip-on-and-off design on the flat sole allows for effortless styling. Pair these sandals with rhinestone fringe earrings for even more glitz!
Fit & Features
- Flat textured sole
- Jelly material
- Round toe
- Thong strap design
- Iridescent gemstones, mini rhinestones
- Slip-on-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1177
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance Me High-Rise Hanky Lace Midi Skirt
Bring the romance to your style in this lace midi skirt - a chic option for birthday dinners or parties! The high-rise waist and slim-fit silhouette flatters your figure, while the flowy hanky uneven midi-length hem adds a playful touch. Made with delicate floral lace fabric with a knit lining, this skirt exudes elegance and charm. Complete the look in a corset top and block heels.
Fit & Features
- Sheer floral lace fabric lined with stretchy knit
- High waist
- Mid-length flowy hanky hem
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 06501-1019
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Irresistible Floral Lace Corset Mini Dress
You'll be simply irresistible with your gorgeous allure in this floral lace corset mini dress. Airy and sheer, the lace fabric is accented with a romantic floral print and includes a partial knit lining for coverage. The mini-length dress is shaped with a feminine sweetheart neckline with a padded bust, and adjustable spaghetti straps for that customized fit. The corset-style bodice features sheer inserts for a hint of skin and has flexible boning for a snatched silhouette. The bodycon fit will flaunt your stunning curves. Complete your date night look with the perfect pair of heels!
Fit & Features
- Floral printed sheer lace fabric with knit lining, moderate stretch
- Sleeveless sweetheart neckline with padded bust
- Adjustable spaghetti straps
- Corset bodice, sheer inserts with flexible boning, high waist seam
- Back zipper with hook and eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3138
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slip Into Luxury Rhinestone Flat Jelly Sandals
Slip into luxury with these jelly sandals on vacation or a weekend spent under the sun! Featuring a sparkling rhinestone band and a comfortable square toe, these slide sandals will add a touch of glamour to any outfit. Made with soft and durable jelly material, they are perfect for slipping on and off. Complete the look with trendy sunglasses.
Fit & Features
- Flat sole
- Jelly material
- Rhinestone embellished strap
- Square toe
- Runs a half-size small, recommend sizing up
Style Number/Barcode: 07404-1186
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Sheen Metallic Woven Faux Leather Sandals
Step out and shine with a glamorous sheen in these metallic woven faux leather sandals! Made with a sleek faux leather material with a glitzy metallic sheen, these sandals feature a square-shaped toe with a wide strap with a trendy abstract woven design. The slip-on-and-off design on the flat sole allows for effortless styling, and the lightly padded insole provides comfortable wear. Pair these sandals with a mini tote bag.
Fit & Features
- Flat sole
- Faux leather upper, metallic sheen
- Square toe
- Wide strap with woven design
- Slip-on-and-off styling
- Lightly padded insole
- Runs true to size
Style Number/Barcode: 07404-1172
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Tropical Print Flowy Maxi Dress
This tropical print flowy maxi dress is giving major weekend getaway energy! The breezy lightweight woven fabric is detailed with a tropical leaf-outlined print, perf for your next vacay. The maxi-length dress features a sleeveless square neckline and adjustable spaghetti straps for a customized fit. The high waist leads to a cute tie-back design, followed by a lower back cutout for a hint of skin. The dress flows out in an A-line silhouette with a stylish tiered design. Complete your look with gold hoops and strappy sandals.
Fit & Features
- Tropical printed woven fabric
- Sleeveless square neckline
- Adjustable spaghetti straps
- High waist with tie-back design, lower back cutout
- Flowy A-line fit with a tiered design
- Runs true to size
Style Number/Barcode: 05102-5609
Category Name: Vacation Looks
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Attention Getter Strapless Newspaper Print Mini Dress
Capture attention with all eyes on you in this fab newspaper print mini dress! The textured lined woven fabric features a newspaper print with rose print accents for that trendy-girl vibe. The strapless straight-across neckline is detailed with an eyelet lace and thin velvet ribbon trim, tying at the center. The bodice features a bust seam outline with ruching to accentuate your figure. The flexible side boning adds structure, while the hidden back zipper offers effortless styling. The form-hugging fit on the mini-length hem will flaunt your stunning curves. Style with a layered choker necklace.
Fit & Features
- Non-stretch textured lined woven fabric, rose newspaper print
- Strapless straight neckline with no-slip strip
- Eyelet lace and velvet ribbon trim, tie-front, bust seam outline with ruching
- Flexible side boning, hidden back zipper with hook and eye closure
- Form-hugging fit
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05102-5644
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Glitz Rhinestone Strap Faux Leather Sandals
Add a glitzy shine to your casual looks with these glam rhinestone strap sandals! Made with faux leather material, these sandals feature an open round toe, followed by a wide banded strap embellished with sparkling mini rhinestones. More rhinestones outline the flat sole. The open back offers effortless on-and-off styling. Pair these sandals with a choker necklace!
Fit & Features
- Faux leather material
- Open round toe
- Wide banded strap
- Rhinestone embellishments
- Open back, flat sole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1187
Category Name: Vacation Looks
Price: $18.90
Availability: Out of Stock
Product Badge:- Ships Free