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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Naturally Cute Strappy Platform Wedges
Naturally, summer calls for cute styles like this platform wedge perfect for hanging poolside or a beach day! It features a square toe, a strappy design, a platform sole, slightly cushioned footbed, and an ankle strap with buckle closure. Complete the look with a breezy kimono.
Fit & Features
- Square toe
- Strappy design
- Platform style
- Ankle strap with buckle closure
- Slightly cushioned footbed
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-0318
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Audience Paisley Wrap Crop Top
Groove until sunset at the concert or party in this paisley crop top perfect summertime fun! It features retro bell long sleeves, a V-neckline, and a customizable wrap-tie hem on stretchy knit fabric. Complete the look in sleek faux leather shorts.
Fit & Features
- Bell long sleeves
- V-neckline
- Wrap-tie cropped hem
- Paisley print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06001-4724
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fit Check Strapless Denim Jogger Jumpsuit
The denim jumpsuit you'll be wearing on rotation! It features a strapless elasticized neckline, hidden side pockets, a high-rise drawstring elasticized waist, and a relaxed jogger-style leg silhouette with elasticized cuffs. Complete the look in clear lucite heels and earrings for happy hour!
Fit & Features
- Strapless elasticized neckline
- Hidden side pockets
- High-rise drawstring elasticized waist
- Relaxed, jogger-style leg silhouette
- Elasticized cuffs
- Light wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06602-0334
Category Name: Vacation Looks
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Gem Of The Sea Faux Pearl Denim Shorts
These statement denim shorts are truly the gem of the sea! They feature a flattering high-rise waist, front distressed accents and faux pearl embellishments, and a raw frayed cut-off hem with distressing. The jean shorts are composed of non-stretch medium wash denim with a color fade effect. Complete the look in a satin tie-front top for an haute night on the town!
Fit & Features
- High-rise waist
- Front distressed and faux pearl embellishments
- Raw frayed cut-off hem, distressing, slim, curve-hugging fit
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim fabric, no stretch, color fade effect
- Runs true to size
Style Number/Barcode: 06603-0326
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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70s Groove Floral Tie-Back Skater Dress
Get into the groove of this 70s-inspired printed floral dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering skater short-length silhouette. Complete the look in rhinestone mules for a dressy date!
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Tie-back design
- Skater silhouette
- Short-length hem
- 70s-inspired floral print
- Woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5053
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Love For Chic Style Heart Hoop Earrings
Show off your love for all things chic with these heart-shaped hoops. The metal earrings feature a bamboo-style texture with a click-top closure. Complete the look with a mini handbag.
Fit & Features
- Metal hoop earrings
- Heart-shaped design
- Bamboo-style texture
- Click-top omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1616
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Resort Calling Mesh Tie Front Top
Booked the trip? This top is already packed. Featuring a tie-front design, long sleeves and a dramatic crop hem, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails.
Shop The Matching Skirt: Resort Calling Mesh Slit Maxi Skirt
Fit & Features
- Floral print, partially lined mesh fabric
- Long sleeves
- Tie-front closure
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06202-000032
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soak Up The Sun Tropical Print Maxi Dress
You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Backless design, single lattice strap
- Flowy floor-length hem, high front slit
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4997
Category Name: Vacation Looks
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smooth Silhouette Crop Tube Top
This smooth tube top is designed to flatter and elevate every look! It features a strapless neckline, a form-hugging fit, and a sleek cropped hem. The double-lined stretchy knit fabric offers a seamless design and has an ultra-buttery feel. Style with the matching bottoms for a chic look!
Shop Matching Blue And Black Bottoms: Smooth Silhouette Bodycon Mini Skirt
Shop Matching Rust Bottoms: Smooth Silhouette Slit Midi Skirt
Fit & Features
- Strapless neckline
- Form-hugging fit
- Cropped hem
- Double-lined, buttery knit fabric
- Seamless design
- Runs true to size
Style Number/Barcode: 06002-1615
Category Name: Vacation Looks
Price: $11.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Me Cute Linen V-Neck Skater Dress
Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruffled underbust trim
- Tiered ruffle layered skater silhouette
- Short-length hem
- Color block pattern
- Airy woven linen fabric, partial lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4994
Category Name: Vacation Looks
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Perfection Straw Clutch
Accessorize all your summer looks with this straw clutch for a perfect casual-chic vibe. It features a rectangular shape, a curved fold-over design, and is composed of a braided straw material. Style with an adorable matching set.
Fit & Features
- Rectangular shape
- Curved fold-over design
- Braided straw material
Style Number/Barcode: 07203-1166
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Stunner Dangly Earrings
Set out to stun with these dangly earrings featuring sun-shaped post and bottom charms with a post-back closure. Complete the look with a dainty anklet for a boho-chic style!
Fit & Features
- Sun-shaped post and bottom charms
- Dangly design
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1626
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Charm Swiss Dot Chiffon Midi Dress
Unlock your sweet charm in this chiffon midi dress perfect for bridal showers, graduation parties, and more! It features a sleeveless V-neck with a twisted bust, adjustable spaghetti straps, a flirty tie-back design, and a flowy silhouette and ruffled hem. The dress is composed of an airy chiffon fabric with a swiss dot pattern and a smooth woven lining. Complete the look in faux pearl heels.
Fit & Features
- Sleeveless V-neck, twisted bust
- Adjustable spaghetti straps
- Tie-back design
- Flowy silhouette, ruffled midi-length hem
- Airy chiffon fabric, swiss dot pattern, smooth woven lining
- No stretch
- Runs true to size
Style Number/Barcode: 05102-5047
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Charming Floral Eyelet Lace Dress
Always charming and cute, this floral eyelet lace dress boasts adorable allure! It features puff short sleeves, a square neck, a tie-back design, and a flattering skater silhouette and short-length hem. Complete the look in strappy sandals for a baby shower or family party.
Fit & Features
- Puff short sleeves
- Square neck
- Tie-back design
- Skater silhouette
- Short-length hem
- Ditsy floral print, eyelet lace, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5030
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready To Ruffle V-Neck Mini Dress
You'll bring the flirty flare with this mini dress for bridal showers or day dates! The dress features a sleeveless ruffle V-neckline, straps with ruffle trim, and a bodycon silhouette on stretchy and smooth knit fabric with lining. Complete the look in trendy flat sandals and a purse!
Fit & Features
- Sleeveless ruffle V-neckline
- Straps with ruffle trim
- Bodycon silhouette
- Mini-length hem
- Stretchy, smooth knit fabric with lining
- Runs true to size
Style Number/Barcode: 05102-5049
Category Name: Vacation Looks
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Allure Sheer Lace Bodycon Mini Dress
Show off a romantic allure in this chic sheer lace bodycon mini dress. It features a sleeveless high crew neckline with a scalloped lace hem that continues throughout the dress, a sheer mesh bust insert with a sultry V-shaped plunging design, a sheer mesh back with a zipper closure, a mini-length hem with a sheer mesh ruffled trim, and a curve-hugging silhouette. The floral lace fabric includes a partial lining. Style with clear heels.
Fit & Features
- Sleeveless high crew neckline, scalloped lace hem
- Sheer mesh bust insert, V-shaped plunging design
- Sheer mesh back, zipper and hook-eye closure
- High waist seam, mini-length hem, sheer mesh ruffled trim
- Bodycon fit
- Sheer floral lace fabric, partial sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2128
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flower Garden Tie Strap Bustier
Fresh and flirty, flaunt your florals on this bustier featuring a sleeveless, square neck, trendy tie-straps, a fitted crop hem, and a back zipper closure. Complete the look in high-rise jeans and sandals for a day date.
Fit & Features
- Sleeveless, square neck, tie-straps
- Fitted crop hem
- Back zipper closure
- Floral print
- Woven fabric, lined, no stretch
- Fits true to size
Style Number/Barcode: 06003-1876
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Love Me Floral Crepe Skort Romper
Love is in full bloom this spring! Embrace the romance in this flirty floral skort romper featuring a sleeveless, criss-cross wrap halter neck with tie closure, front cutout bodice, and a ruffled skort-style bottom. Complete the look in lace-up heels for a dressy occasion.
Fit & Features
- Sleeveless, criss-cross wrap halter neck, tie closure
- Front cutout bodice
- Ruffled skort-style bottom
- Partial open-back, smocked panel, zipper closure
- Floral print crepe-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06303-0197
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crochet Cutie Long Sleeve Crop Top
You'll be the cutest gal at festivals or country bars in this crochet crop top featuring sheer fitted long sleeves, a square neck, front cutout accents, and a dual tie-back closure. Style with printed flare pants and a hat to complete the look!
Fit & Features
- Sheer fitted long sleeves
- Square neck
- Front cutout accents
- Ultra-cropped hem
- Dual tie-back closures
- Crochet knit, sheer design, no stretch
- Runs true to size
Style Number/Barcode: 06005-1631
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ticket To Flirty Ditsy Floral Mini Dress
Your ticket to looking fun and flirty is this ditsy floral mini dress perfect for a staycation or weekend getaway! It features a sleeveless sweetheart neckline, spaghetti straps, a front bust tie with a keyhole accent, and a bodycon silhouette. The soft brushed knit fabric offers plenty of stretch. Complete the look in heeled sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Front bust tie, keyhole accent
- Bodycon silhouette, mini-length hem
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5115
Category Name: Vacation Looks
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt on Repeat Ruffle Skort
Made to twirl, tease, and totally steal the spotlight. This ruffle mini skort is flirty with just enough edge—and yes, it comes with built-in shorts so you can actually move.
Fit & Features
- Abstract print, mesh fabric, stretchy knit shorts lining
- Mid-rise waist
- Form-hugging fit
- Ruffled mini skirt overlay
- Runs true to size
Style Number/Barcode: 06503-000114
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: L
Product Badge:- Sale
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Casually Cute Floral Off-The-Shoulder Dress
Step out looking casually cute in this floral mesh mini dress for lunch with the girls or a bridal shower! It features an off-the-shoulder neckline, sheer short-sleeve cuffs, a ruched bust, and side, and back ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a dainty ring set and heels.
Fit & Features
- Off-the-shoulder neckline
- Sheer short-sleeve cuffs
- Back zipper and hook-eye closure
- Ruched bust, side and back seams
- Bodycon silhouette, mini-length hem
- Ditsy floral print, mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4914
Category Name: Vacation Looks
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Braided Beauty Straw Strappy Flat Sandals
Create an effortless summer look in these flat sandals perfect for a beach day, vacations, and casual plans! They feature a square toe, a strappy straw braided design, a flat sole, and a faux leather material. Complete the look in cute sunglasses.
Fit & Features
- Square toe
- Strappy straw braided design
- Flat sole
- Slightly cushioned footbed
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1086
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mojito Please Tropical Halter Jumpsuit
This tropical halter jumpsuit is ready for sippin' mojitos and dancing the night away on your next vacay! It features a sleeveless halter neckline with tie-back straps, a cutout bodice, a partially open back, and a hip-hugging slim-leg silhouette. Complete the look in espadrille wedges.
Fit & Features
- Sleeveless halter neckline, tie-back straps
- Cutout bodice, partially open back
- Hip-hugging, slim-leg silhouette
- Tropical palm print
- Smooth knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06502-2311
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance