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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Summer Love Floral Mini Dress
You'll fall head over heels for this floral mini dress that brings the romantic vibes. It features a sleeveless V-neckline, spaghetti straps, a flattering high waist seam, side ruched detailing with a drawstring, and a short, curve-hugging fit with an asymmetrical hem. Style this dress with clear heels.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- High waist seam
- Side ruching, drawstring at hem
- Mini-length, form-hugging silhouette, asymmetrical hem
- Knit fabric, plenty of stretch, floral print
- Runs true to size
Style Number/Barcode: 05101-1112
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miss Trendsetter Rimless Rectangle Sunglasses
Set out to make a trendy moment in sunnies that slay! The sunglasses feature a rimless frame, rectangular-shaped lenses, nose pads, and sleek metal arms. Complete look with a bodysuit and high waist jeans.
Fit & Features
- Rimless frame
- Rectangular-shaped lenses
- Nose pads
- Sleek metal arms
Style Number/Barcode: 07008-0881
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So The Drama Oversized Sunglasses
These sunnies are for the dramatic babes out there looking to make a bold statement! The sunglasses feature a rimless frame, stud accents, oversized square lenses, nose pads, and sleek metal arms. Complete look with a jumpsuit and heels.
Fit & Features
- Rimless frame
- Stud accents
- Oversized square lenses
- Nose pads
- Sleek metal arms
Style Number/Barcode: 07008-0882
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Shady Vibes Ombre Sunglasses
Channel those shady vibes with a stylish pair of sunnies! The sunglasses feature rimless frames, geometric-shaped lenses, ombre lenses, nose pads, and sleek arms. Complete look with a floral swimsuit and sandals.
Fit & Features
- Rimless frames
- Geometric-shaped lenses
- Ombre lenses
- Nose pads
- Sleek metal arms
- 100% UV protection
Style Number/Barcode: 07008-0879
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flutter On Butterfly Charm Belly Chain
Flutter on with a pretty belly chain to accent your swimsuits! The belly chain features a dainty chain link adorned with mini butterfly charms.
Fit & Features
- Dainty chain link
- Mini butterfly charms
- Lobster clasp closure
Style Number/Barcode: 07301-0312
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Chic Smocked Maxi Dress
Capture those effortlessly chic vibes in this maxi dress! The dress features a square neckline, short sleeves, and a smocked bodice. The maxi length silhouette features a button-down center and a mini skirt length lining. The dress is composed of a smocked knit fabric and lightweight woven fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.
Fit & Features
- Square neckline, short sleeves
- Smocked bodice
- Button-down center
- Maxi length silhouette
- Mini skirt length knit lining
- Smocked knit, lightweight woven fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4113
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold And Breezy Door Knocker Earrings
These intertwined door knocker earrings are the perfect mix of bold and breezy, ready to elevate your weekend ‘fit or vacay vibe.
Fit & Features
- Metal material
- Round door knocker silhouette
- Linked double-ring design
- Intertwined wrapped fabric detailing
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000035
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Romance Asymmetrical Mini Dress
Fall in love with this dreamy tropical printed mini dress that is a must-have for summer vacays. It features a sleeveless V-neckline, adjustable spaghetti straps, side ruched detailing, and a mini-length, curve-hugging silhouette with a trendy asymmetrical hem. Style this dress with cute mules.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Side ruched detailing
- Short, form-hugging fit
- Asymmetrical hem
- Brushed knit fabric, plenty of stretch, tropical palm leaf print
- Runs true to size
Style Number/Barcode: 05102-1857
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Rise Cutoff Denim Shorts
Elevate your denim game with cutoff shorts that are perf for that next bonfire with the squad! The shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, moderate distressing, and a cutoff hem with fringe. Complete look with a crop top and huggies.
Fit & Features
- High rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Moderate distressing
- Cutoff hem, fringe
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0178
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hello Summer Woven Tote
Welcome summer with a cute tote to bring to brunch! The tote features a wooden O-ring handle and a crochet woven body. Complete look with a floral top and skirt set.
Fit & Features
- Wooden O-Ring handle
- Crochet woven body
Style Number/Barcode: 07203-0687
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Woven Sandals
Get away with these chic sandals! The sandals feature an open square toe, a woven strap over the toe, and a low block heel. The sandals are composed of a faux leather material. Complete look with a matching set
Fit & Features
- Open square toe
- Woven strap over the toe
- Low block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0803
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Triple Threat Faux Leather Block Heels
Step up your heel game with bold block heels! The heels feature a zippered back, a triple strap design, an open almond toe, and a stacked block heel. The heels are composed of a faux leather material. Complete look with a romper and a dainty chain link necklace.
Fit & Features
- Zippered back
- Triple strap design
- Open almond toe
- Stacked block heel
- Faux leather material
Style Number/Barcode: 07401-2990
Category Name: Vacation Looks
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keepin' Knit Retro Tie Dye Sneakers
Keep it retro with these fab sneakers! The sneakers feature a lace-up front, pull tab at the back of the ankle, a tie-dye print, a knit body, and a jelly sole. Complete your look with a bodysuit and high waist shorts.
Fit & Features
- Lace-up front
- Pull tab at back
- Tie-dye print
- Knit body
- Jelly sole
Style Number/Barcode: 07407-0208
Category Name: Vacation Looks
Price: $7.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Triple Band Open Toe Sandals
Slay in basic sandals that are perf for everyday! The sandals feature an open back, an adjustable ankle strap, a triple-strap design, and an open almond toe. Complete look with a matching set.
Fit & Features
- Open almond toe
- Open back
- Adjustable ankle strap
- Triple-strap design
- Runs true to size
Style Number/Barcode: 07404-0775
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Put A Ring On It Cutout Mini Dress
Put a ring on this cute mini dress that is a must for your next night out! The dress features a plunging sleeveless V-neckline, dual cutouts at the waist, an O-Ring at the center of the bodice, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless V-neckline
- Cutouts at the waist
- O-Ring
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2139
Category Name: Vacation Looks
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Vibes Sleeveless Mini Dress
Showcase a gorgeous glow in this sunset-hued tie-dye mini dress! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. The brushed knit fabric offers plenty of stretch. Style this dress with a denim jacket and sneakers for a casual look.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Mini-length, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1483
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemian Days Paisley Tie Front Top
Make your day a bohemian-inspired one with a cute tie-front top! The top features a plunging V-neckline, a tie-front accent, long sleeves, and a cropped hem. The top features a bohemian-inspired paisley print that pairs perfectly with your favorite sandals!
Fit & Features
- V-neckline
- Tie-front accent
- Long sleeves
- Cropped hem
- Paisley print
- Gauze knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-0936
Category Name: Vacation Looks
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sheer Appeal High Slit Halter Dress
Bring some serious sheer appeal with a maxi dress that wows! The dress features a halter neck with a plunging keyhole, halter neck tie, and a maxi-length silhouette with a high side slit. The dress is composed of a sheer mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a chic updo.
Fit & Features
- Halter neck
- Plunging keyhole
- Halter neck tie
- Maxi length silhouette
- High side slit
- Mesh fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1203
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Burst Tie Dye Mini Dress
Add a burst of color to your look with this fab mini dress! The dress features a tie-dye print, sleeveless square neckline, bungee straps that cross at the back, lace-up straps, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear heels.
Fit & Features
- Sleeveless square neckline
- Bungee straps, cross at the back
- Lace-up straps
- Mini length silhouette
- Tie-dye print
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4114
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stacked On Style Faux Leather Stacked Heels
Step up your heel game with bold stacked heels! The heels feature a zippered back, a triple strap design, an open almond toe, and a stacked block heel. The heels are composed of a faux leather material. Complete look with a romper and a dainty chain link necklace.
Fit & Features
- Zippered back
- Triple strap design
- Open almond toe
- Stacked block heel
- Faux leather material
Style Number/Barcode: 07401-2991
Category Name: Vacation Looks
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool It Tie Front Crochet Vest
Add a stylish twist to your look with this crochet vest. Featuring a delicate crochet pattern and a flattering tie-front closure, this vest offers both comfort and charm.
Fit & Features
- Crochet knit sheer fabric
- Tie front closure design
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-000016
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylishly Studded Faux Leather Sandals
These stylishly studded faux leather sandals are perf for getting a trendy summertime look! They feature an open round toe, a wide criss-cross strap design, a chic studded trim, and a flat sole. Complete the look with aviator sunglasses.
Fit & Features
- Open round toe
- Wide criss-cross strap design
- Studded trim
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0755
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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By The Beach V-Neck Halter Babydoll Crop Top
Enjoy a sunny day by the beach in this breezy babydoll crop top with a pretty eyelet V-neckline and a flowy silhouette. Perfect for styling as a cover-up or by itself.
Fit & Features
- Cotton woven fabric
- Adjustable spaghetti straps
- V-neckline, eyelet bust
- Stretchy smocked back panel
- Flowy uneven crop hem
- Runs true to size
Style Number/Barcode: 06003-2763
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Daydream Mesh Mini Dress
You'll look like such a daydream in this trendy tie-dye mini dress! It features a sleeveless scoop neckline, spaghetti straps, a twist-back design, a short, curve-hugging silhouette, and a subtle all-over tie-dye print in pretty pastel hues. Style this dress with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Twist-back design
- Mini-length, form-hugging fit
- Mesh fabric, tie-dye print, pastel hues
- Runs true to size
Style Number/Barcode: 05102-4131
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale