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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Oh Snap Button Henley Bodysuit
Slay all day in this essential henley bodysuit you'll love styling with day or night fits! The sweater rib knit bodysuit features long fitted sleeves, a plunge V-neckline, three snap-button front closures, and a thong-cut bottom with snap-button closures. Complete the look in new denim jeans and knee-high boots.
Fit & Features
- Long fitted sleeves
- Plunge V-neckline
- Three snap-button front closures
- Thong bottom
- Dual snap-button closures
- Sweater rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1592
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Eye-Catching Pop Strappy Thong Stiletto Sandals
Perfect for adding eye-catching style, these stiletto sandals give every outfit the pop it needs! With a square toe, thong toe strap, and short stiletto heel, these faux leather sandals are as stylish as they are comfortable. The strappy adjustable ankle with buckle closure adds an elevated allure and a secure fit. Complete the look with a trendy shoulder bag for any occasion!
Fit & Features
- 3.5" Stiletto heel
- Faux leather material
- Thong toe strap
- Strappy adjustable ankle, buckle closure
- Runs true to size
Style Number/Barcode: 07401-4838
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Vibes Wide-Leg Palazzo Pants
These breezy woven palazzo pants will give off those effortless weekend vibes with their relaxed, wide-leg silhouette. Style with the matching tie-front crop top for a chic look.
Shop Matching Top: Weekend Vibes Tie-Front Crop Top
Fit & Features
- Woven fabric
- High-rise waist
- Dual front pockets
- Pleating
- Flowy wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-000004
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easygoing Chic Puff Sleeve Tie Front Top
You'll feel easygoing and chic in this linen-like top for any weekend plans or on vacay! With its playful puff sleeves and breezy open front design featuring dual tie-fronts, this top is the perfect addition to your summer wardrobe. Pair with the matching skort.
Fit & Features
- Linen-like woven fabric, sewn-in knit lining
- Puff short sleeves
- Open front design, dual tie-front
- keyhole back with button closure, stretchy smocked panel
- Mid-length hem
- Runs true to size
Shop The Matching Skort: Easygoing Chic High-Rise Wrap Tie Skort
Style Number/Barcode: 06003-000003
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Constant Stunner Open Back Halter Crop Top
You'll always stun in this sexy halter crop top boasting an open back and front design that leaves many speechless!
Fit & Features
- Eyelet floral embroidery, woven-lined fabric
- Halter plunge neckline
- Open front design
- Cropped hem
- Open back with spaghetti strap tie
- Runs true to size
Style Number/Barcode: 06003-2742
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Twist Tie-Back Striped Midi Dress
A chic twist on a classic sundress. This head-turning midi dress is designed with an open tie-back with button accents and hidden side pockets that keep your hands warm!
Fit & Features
- Striped print, woven fabric, woven lining
- V-neckline
- Spaghetti straps
- Open tie-back design, lower button accents
- Hidden side pockets
- A-line silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000022
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Summer Sweetheart Ruffled Eyelet Midi Dress
Looking for the perfect summer dress? Look no further than this playful sleeveless midi dress! With its flattering sweetheart neckline with a structured bust and adjustable spaghetti straps, this A-line silhouette dress will have you feeling confident and stylish. The ruffled midi-length hem and floral embroidered eyelet woven fabric add a touch of playfulness to this must-have dress! Complete the look with wedge sandals.
Fit & Features
- Floral embroidered eyelet woven fabric, stretchy knit lining
- Sweetheart neckline, padded bust with underwire
- Adjustable spaghetti straps, back zipper with hook and eye closure
- High waist seam, A-line silhouette
- Ruffled midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3015
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Mood Strappy Faux Leather Block Heel Mules
These strappy faux leather block heel mules will put you in a chic mood! The low-block heels are composed of smooth faux leather material and feature an open square-shaped toe with a thin knotted strappy design across the foot for a trendy look. Include an open back for easy on-and-off styling. Pair these mules with a mini handbag!
Fit & Features
- 3" Block heel
- Faux leather material
- Open square toe
- Knotted strappy design
- Open back
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4760
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiss The Sun Tropical Lace-Up Slit Maxi Dress
Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.
Fit & Features
- Tropical print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up back
- Form-hugging silhouette, high front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6103
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine Cutie Strapless Ruffle Eyelet Mini Dress
Created for the cuties, this eyelet mini dress is a cute look for shower celebrations or casual parties! Designed to hug your form for a flattering fit, the strapless neckline and ruffled mini hem add a flirty and playful touch.
Fit & Features
- Eyelet fabric, stretchy knit lining
- Strapless neckline
- Form-hugging fit
- Ruffled layer mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000187
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Flirt Lace-Up Heeled Thong Sandals
The perfect faux leather sandals for a flirty look with all your sundresses! These exclusive thong sandals showcase a sleek square toe with a thong-style strap, a thin block heel, and thin lace-up straps that let you customize the style. Complete the look with a trendy handbag for any occasion!
Fit & Features
- 3.5" Thin block heel
- Faux leather material
- Square toe, thong strap
- Lace-up straps
- Runs true to size
Style Number/Barcode: 07401-4810
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Mode Buckle Cutout Slit Maxi Dress
A must-have maxi dress for any fashion-forward traveler! Featuring a sweetheart neckline with a trendy buckle accent, a sultry cutout bodice, and a high side slit, this dress will hug your curves and make you feel stylish on your vacation.
Fit & Features
- Texture knit fabric, smooth knit stretchy lining
- Sweetheart neckline with buckle accent
- Spaghetti straps
- Cutout bodice
- High side slit
- Form-hugging fit, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6082
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crush On You Sleeveless V-Neck Skater Dress
Everyone will end up with a crush on you in this sleeveless skater dress perfect for beach days or backyard parties! This playful dress features adjustable drawstring shoulder straps and a flattering V-neckline and back design. The fitted waist and skater silhouette create a feminine and flirty look along the short-length hem. Complete the look in heeled sandals.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- Adjustable drawstring shoulder straps
- V-Neckline and back
- Fitted waist, skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5500
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Trend Crew Neck Bodycon Midi Dress
A sleeveless midi dress that'll keep you majorly trendy! Perfect for casual plans or vacations, this midi dress is designed with a flattering crew neckline, bodycon silhouette, and front ruched seam, this dress will accentuate your figure. The front slit adds a touch of drama, while the rib knit fabric offers a sewn-in knit lining for extra coverage. Complete the look with chic sandals and sunnies!
Fit & Features
- Rib-knit stretchy fabric, sewn-in knit lining
- Bodycon silhouette
- Front ruched seam and slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5596
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Juicy Drama Cherry Earrings
These cherry earrings know how to steal the spotlight. Serve juicy drama with every head turn, whether you're posting or partying!
Fit & Features
- Cherries with sleek stems
- Pull-through design
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000098
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free
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Finders Keepers V-Neck Tie Midi Dress
Once you find this sleeveless midi dress you'll want to keep it! Perfect for semi-formal occasions, this midi dress will make you feel chic and effortless. Designed with an adjustable V-neckline with a bust tie, sleek spaghetti straps, and a flattering curve-hugging silhouette that exudes charm. Complete the look with a bolero shrug sweater and strappy stilettos!
Fit & Features
- Woven fabric, no stretch
- Spaghetti straps
- Adjustable bust tie
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5551
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Intentions Sleeveless Knit Mini Dress
Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!
Fit & Features
- Knit fabric with moderate stretch
- High square neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1881
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Bliss Rib Knit Pajama Pants
Experience comfort and bliss in these soft pajama pants! Its elasticized drawstring high-rise waist, wide-leg silhouette, and soft rib knit fabric ensure a cute and cozy lounge. Complete the look with the matching pajama top.
Shop Matching Top: Feeling Bliss Rib Knit Pajama Tank Top
Fit & Features
- High-rise elasticized drawstring waist
- Wide-leg silhouette
- Soft rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0955
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- High-rise elasticized drawstring waist
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Sunny Thoughts Sleeveless Cutout Crochet Maxi Dress
Get summer vibes in an instant wearing this crochet maxi dress perfect for vacation or strolling the boardwalk! Featuring a flattering square neckline, spaghetti straps, and a stunning cutout back with an adjustable drawstring insert and a front slit for movement along the maxi-length silhouette. Complete the look with sunglasses and sandals.
Fit & Features
- Crochet knit fabric lined with stretchy knit
- Spaghetti straps
- Square neckline
- Cutout back, adjustable drawstring insert
- Front slit
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5742
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty Blooms Floral Mesh Halter Maxi Dress
Showcase your beauty in this lined mesh maxi dress accented with a large floral print for a pretty vibe. It features a sleeveless cowl neckline, halter tie-back spaghetti straps with beaded detailing, an open back with lower tie-back straps, and a maxi-length hem with a form-hugging fit to highlight your curves.
Fit & Features
- Sheer mesh fabric with knit lining
- Large floral print pattern
- Cowl neckline
- Halter tie-back spaghetti straps, beaded details
- Open back, lower tie-back spaghetti straps, beaded details
- Maxi-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5988
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Western Moves Sweetheart Denim Skater Mini Dress
Show off your Western style in this denim skater mini dress for dancing in the desert at festivals or concerts!
Fit & Features
- Denim fabric, stretchy knit lining
- Sweetheart neckline, underwire bust
- Adjustable spaghetti straps
- Back zipper closure
- Bodycon bodice
- Skater chiffon lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6018
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Sweet Floral A-Line Mini Dress
Sunny sweet will be your vibe in this cute floral mini dress designed with a strapless neckline, ruching, and a hanky hem A-line silhouette.
Fit & Features
- Knit fabric, high stretch
- Small floral print
- Strapless straight neckline
- Ruching
- Drop waist
- Mini-length hanky hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000008
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Style Acrylic Bangle Bracelet
Low-effort, high-impact vibes. This acrylic bangle bracelet is your go-to for adding a bold, minimal twist to any look—stack it up or wear it solo for instant cool.
Fit & Features
- Acrylic material
- Thick bangle silhouette
- Slip-on design
Style Number/Barcode: 07003-000125
Category Name: Vacation Looks
Price: $2.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Let's Get Away Open Back Sleeveless Crop Top
This sleeveless crop top is exactly what you need for a casual vacay or weekend look! Made with double-lined brushed knit fabric, this top is both soft and durable. The square neckline and open-back twist design create a trendy look, while the fitted crop hem provides a flattering silhouette. Complete the look in jean shorts and sandals!
Fit & Features
- Double-lined brushed knit stretchy fabric
- Twist open back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-5250
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale