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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Sunny Dreams High-Rise Distressed Denim Shorts
Keep it cute and casual all season in these denim shorts from fun at the beach to weekend hangs! They feature a flattering high-rise waist, trendy distressed accents along the form-hugging silhouette, and a raw cut-off hem. Complete the look in a basic tee and sneakers!
Fit & Features
- Denim material with stretch
- High-rise waist
- Distressed accents
- Form-hugging
- Front button and hidden zipper closure
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-0397
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Poolside Flirt String Bikini Top
Sit flirty and pretty in this eyelet string bikini top at a pool party or on vacation! Pair with the matching bikini bottoms.
Fit & Features
- Eyelet lined fabric
- Triangle cups
- Dual string spaghetti back ties
- Runs true to size
Shop The Matching Bikini Bottoms: Poolside Flirt Eyelet String Bikini Bottoms
Style Number/Barcode: 07104-0719
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serve Attitude Cat Eye Sunglasses
These aren’t just sunglasses—they’re your armor of IDGAF. With a sleek cat eye shape that oozes retro cool and mystery, these frames instantly upgrade your fit and your mood.
Fit & Features
- Cat eye frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000065
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Striped Halter V-Neck Mini Dress
This striped mini dress will easily become your perfect favorite piece this season! The halter V-neckline and open back highlight your alluring figure, while the bodycon fit and mini-length hem flatters your curves on the striped mesh-lined fabric. Complete the look with sunglasses and sandals for a day out or on vacation!
Fit & Features
- Striped print, mesh fabric, soft stretchy knit lining
- Halter V-neckline
- Open back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5811
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Chic High Slit Crochet Maxi Skirt
Create a sunny chic 'fit with the cutest crochet maxi skirt! Designed with a breezy sheer crochet knit fabric with a built-in panty lining, this skirt was made for summer getaways. It features a high-rise banded waist with a front adjustable drawstring for a customized fit, a high-cut back slit, and a slim-fit silhouette. Complete your look with the matching crop top and a pair of slip-on sandals!
Shop Matching Top: Sunny Chic Halter Ruched Crochet Crop Top
Fit & Features
- Sheer crochet knit fabric, moderate stretch
- Built-in knit panty lining
- High-rise elastic banded waist
- Front adjustable drawstring
- High back slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 06501-0917
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Vibes High Slit Tropical Knit Maxi Dress
Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!
Fit & Features
- Stretchy knit fabric with a bust lining
- Tropical print
- Sleeveless V-neckline
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5537
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Covetable Charm V-Neck Ruffled Maxi Dress
You'll covet the charm of this sleeveless maxi dress all season! With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.
Fit & Features
- Woven fabric, bust lining, no stretch
- Adjustable spaghetti straps
- Crisscross and smocked back
- Flowy silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5546
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Think Sunshine Long Sleeve Cutout Crochet Mini Dress
Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!
Fit & Features
- Crochet fabric, sewn-in knit lining, slight stretch
- Sheer flared long sleeves
- V-neckline
- Hoop insert, cutout waist and back
- Tie-back design
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5732
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Company Sleeveless Button-Up Vest
Never worry about looking stylish with this sleeveless vest in your lineup! Designed from a linen-blend woven fabric, this vest offers a classic and trendy vibe with a collar neckline, button-up front closures, faux pockets, and a cropped hem. Complete the look in denim shorts.
Fit & Features
- Linen-blend woven fabric, no stretch
- Collar neckline
- Button-up front closures
- Buttoned chest pockets
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1785
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Meant To Be Surplice V-Neck Strappy Chiffon Romper
This chiffon romper was meant to be adored by everyone at showers or celebrations! The surplice V-neckline and adjustable spaghetti straps provide a flattering fit, while the crisscross open back adds a touch of playful charm. The tie waist cinches in at the perfect spot, and the layered ruffled short-length hem adds a flirty and feminine touch. Complete the look in wedge sandals.
Fit & Features
- Textured chiffon fabric, chiffon woven lining
- Surplice V-Neckline, adjustable spaghetti straps
- Criss-cross open back, zipper and hook-eye closure
- Layered ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06403-0418
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Daydream Butterfly Chain Belt
Soft girl energy? Activated. This butterfly chain belt flutters right into your faves with dreamy layered charms and delicate movement—perfect for cinching your waist with a little fairycore flair.
Fit & Features
- Chain-link design
- Small and large butterfly charm accents
- Adjustable fit with lobster clasp closure
Style Number/Barcode: 07301-000144
Category Name: Vacation Looks
Price: $3.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty In Paradise One-Shoulder Tropical Maxi Dress
You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.
Fit & Features
- Stretchy knit fabric, knit lining at the bust
- Tropical print
- Asymmetric one-shoulder neckline, spaghetti strap
- Ruched side cutout, adjustable drawstring
- High side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5542
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Prowl Strapless Zebra Crop Top
On the prowl and ready to unleash fierceness in this zebra print crop top! It features a strapless neckline, a tie-back design, and a fitted crop hem that flaunts your figure. Complete the look with the matching skirt.
Shop Matching Skirt: On The Prowl High Rise Zebra Maxi Skirt
Fit & Features
- Zebra print, woven fabric, bust knit lining
- Strapless neckline
- Tie-back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-2507
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Never A Dull Moment Strapless Cutout Maxi Dress
Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Cutout bust, strappy back
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5766
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress
Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.
Fit & Features
- Palm leaf tropical and border print, woven fabric with lining, no stretch
- V-neckline
- Spaghetti straps
- Lace-up back
- A-line maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5864
Category Name: Vacation Looks
Price: $11.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Sun Floral Bikini Bottoms
Enjoy the sweet sunshine at the pool or beach in these floral bikini bottoms! Pair with the matching bikini top.
Fit & Features
- Floral print, knit lined fabric
- Low-rise waist
- Ruffle trim
- Cheeky bottom
- Returns are not accepted without the hygienic liner
- Runs true to size
Shop The Matching Bikini Top: Sweet Sun Floral Tie-Front Bikini Top
Style Number/Barcode: 07105-0867
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Queen High-Rise Slit Tropical Maxi Skirt
Unleash your inner vacation queen with this tropical maxi skirt! Made from stretchy knit fabric, this skirt is perfect for any tropical adventure with its eye-catching palm print. Its high-rise waist and flowy silhouette will flatter your figure, while the high front slit adds a touch of sass. Complete the look with sandals.
Fit & Features
- Tropical palm print, stretchy knit fabric, bikini brief lining
- High rise waist
- High front slit
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-0967
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All-Day Slay Oversized Cat-Eye Sunglasses
Show off an all-day slay in these sleek cat-eye sunglasses! They feature an oversized cat-eye design with a thin metal frame, sassy leopard-printed arms, and tinted lenses. Style these chic shades with hoop earrings.
Fit & Features
- Oversized cat-eye design
- Thin metal frame
- Leopard-printed arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1066
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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City In Style Rhinestone Trim Sunglasses
Stroll the city in these stylish sunglasses for a trendy allure. They feature tinted lenses with rhinestone trim for a hint of glam, rubber nose supports, and a comfortable fit. Complete the look in a basic midi dress for shopping and grabbing coffee!
Fit & Features
- Tinted lenses with rhinestone trim
- Rubber nose supports
- Comfortable fit
- 100% UV protection
Style Number/Barcode: 07008-1079
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Distraction Low Rise Ruffled Mini Skirt
Be a playful distraction in this low-rise mini skirt this summer! Crafted from jacquard pattern woven fabric, it's the perfect way to make a stylish statement with a touch of whimsy. Features a low-rise waist paired with a tiered ruffled silhouette creating a flirty mini-length hem. Complete the look in a crop top and platform sneakers!
Fit & Features
- Jacquard pattern, woven fabric lined with stretchy knit
- Low rise waist
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06401-0674
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Babe Ditsy Floral Cropped Tube Top
Radiate sunny vibes in the cutest cropped tube top! Designed with an adorable ditsy floral print on stretchy smocked knit fabric, it features a strapless straight-across neckline, a cropped hem, a dainty ruffled trim, and a form-hugging fit. Style with denim shorts and sneakers.
Fit & Features
- Ditsy floral print
- Stretchy smocked ribbed knit fabric
- Strapless straight neckline
- Cropped hem
- Ruffled trims
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-1901
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Living In The Palms Wide Leg Palazzo Pants
Escape to a tropical island in these breezy palm print palazzo pants perfect for dinners with a view or exploring with a cocktail in hand! These pants have a flattering high-rise elastic waistband and wide-leg silhouette for style and comfort on stretchy knit palm print fabric. Complete the look with the matching top.
Shop Matching Top: Living In The Palms Tie-Front Crop Top
Fit & Features
- Palm print, stretchy knit fabric
- High-rise elastic waistband
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2462
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crushin' On You Lace Trim Babydoll Floral Crop Top
Look and feel like a precious flirt in this babydoll crop top! Made from an airy mesh fabric with an adorable floral print, this top features a delicate lace trim V-neckline, spaghetti straps, and a layered ruffled crop hem. Complete the look in denim shorts and sandals for casual plans!
Fit & Features
- Floral print, mesh fabric, bust lining
- Spagehtti straps
- Lace trim V-neckline
- Layered ruffled crop hem
- Runs true to size
Style Number/Barcode: 06001-5413
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Prowl High Rise Zebra Maxi Skirt
On the prowl and ready to unleash fierceness in this zebra print maxi skirt! It features a flattering high-rise waist with an elastic banded back for added stretch, a high front slit to show some leg, and a flowy maxi silhouette. Complete the look with the matching top.
Shop Matching Top: On The Prowl Strapless Zebra Crop Top
Fit & Features
- Zebra print, woven fabric
- High-rise waist with elastic banded back
- High front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 06301-0191
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale