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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Compliment Worthy Oval Hoop Earrings
It's easy to look compliment-worthy with these oval hoop earrings that give every outfit a perfect statement! Complete the look in trendy sandals for any occasion.
Fit & Features
- Oval hoops
- Omega closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2022
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Appeal Mock Neck Bodycon Mini Dress
A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!
Fit & Features
- Fitted long sleeves
- Mock neck
- Bodycon silhouette
- Mini-length hem
- Cotton-blend knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5153
Category Name: Vacation Looks
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Aurora Ruffle Lace Crop Top
Capture a flirty aurora in this lace crop top to romance your favorite bottoms! The sleeveless square neckline with ruffle trim adds a touch of charm, while the cropped hem and delicate lace fabric create a playful and feminine look. Complete the look in best-selling bottoms and heels for day or night plans!
Fit & Features
- Lace-lined fabric, no stretch
- Ruffle trim
- Back zipper closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2434
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Mode Halter Cutout Maxi Dress
Amp up the sultry vibes of your summer 'fits with this sleek knit maxi dress featuring a halter square neck, an asymmetric waist cutout, and a curve-hugging silhouette.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Sleeveless square neckline
- Tie-back halter spaghetti straps, partially open back
- Asymmetric side cutout
- Ruching
- Maxi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000051
Category Name: Vacation Looks
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Mode Tropical Print One-Shoulder Maxi Dress
You'll be on vacay mode in this sultry tropical print maxi dress featuring a one-shoulder neckline with a chic O-ring accent and an alluring bust cutout. The floor-length fitted silhouette will flaunt your stunning curves.
Fit & Features
- Mesh fabric, high stretch, knit lining
- Tropical print
- Sleeveless one-shoulder neckline, O-ring accent
- Asymmetric bust cutout
- Asymmetric back strap
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000050
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dressed To Lounge Chenille Knit Catsuit
Get dressed to lounge in this chenille knit catsuit for a night in! The catsuit features a sleeveless square neckline, spaghetti straps, a flirty low scoop back, a form-hugging fit, and a skinny-leg design on ultra-soft and cozy chenille knit fabric. Complete the look in a cozy lounge sweater and slippers!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Low scoop back
- Form-hugging fit
- Skinny-leg design
- Ultra-soft chenille knit fabric
- Runs true to size
Style Number/Barcode: 07103-0948
Category Name: Vacation Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fun In Floral Lace Mini Dress
So fun in floral print, this lace dress is featured in a form-hugging A-line silhouette and playful mini-length hem. Pair with cute wedge sandals for a cute summer look!
Fit & Features
- Floral print, lace fabric, stretchy knit lining
- Square neck with bust tie
- Adjustable spaghetti straps
- Form-hugging A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6015
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Look Puff Sleeve Ruffled Skater Dress
Create a charming look for weekend brunch in this eyelet knit skater dress with the cutest puff sleeves and ruffled mini-length silhouette!
Fit & Features
- Eyelet knit fabric, stretchy knit lining
- Square neckline
- Short puff sleeves, ruffled hems
- Drop waist
- Tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000075
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Stylish Sleeveless Ribbed Knit Midi Dress
Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- High front slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1645
Category Name: Vacation Looks
Price: $38.90
Availability: In Stock
Available Color: WHITE, BLACK
Available Size: M, L, S
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So Fresh Lace-Trim Linen Cropped Tank Top
Keep your casual summer 'fits fresh with this lace-trim linen cropped tank top. Designed with a lightweight linen-blend fabric, this top is perfect for creating effortless everyday looks. It features a low V-neckline accented with a tie-front design leading to a center front slit, tank shoulder straps, a dainty eyelet lace trim for a soft girl vibe, and a fitted cropped hem. Style with light-wash denim and a layered necklace.
Fit & Features
- Linen-blend fabric with woven lining, no stretch
- V-neckline, tie-front design, center front slit
- Tank straps
- Eyelet lace trim
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2384
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lively Elegance Smocked Floral Babydoll Dress
You'll fall in love with this breezy floral babydoll dress, so adorable for weekend parties and graduations! With its stretchy smocked bodice and adjustable straps, you'll get the perfect fit. The chiffon fabric and pretty floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem.
Fit & Features
- Floral printed chiffon fabric, stretchy knit lining
- Square neckline
- Stretchy smocked bodice
- Adjustable spaghetti straps
- Babydoll silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05102-6062
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Center Stage High-Rise Acid Denim Skort
Take center stage in this acid denim skort to rock out at concerts or festivals! Made from a denim fabric with an edgy acid wash rinse, this skort features a flattering high-rise waist, a front envelope skirt overlay for added flair, and a form-hugging mini silhouette. Complete the look in a cute strapless top and boots.
Fit & Features
- Acid wash rinse, denim fabric, slight stretch
- High-rise waist
- Front envelope skirt overlay, form-hugging
- Front button and hidden zipper closure
- Back pockets
- Runs true to size
Style Number/Barcode: 06603-0356
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Got The Look Sleek Aviator Sunglasses
Get a coveted cool-girl look in these sleek aviator sunglasses! They feature a metal frame, tinted lenses, rubber nose supports, and a comfortable fit. Complete the look in a cool denim jacket.
Fit & Features
- Metal frame
- Tinted lenses
- Rubber nose supports
- Comfortable fit
Style Number/Barcode: 07008-1080
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Chic Sleeveless Wrap Mini Dress
You'll look forever chic in this sleeveless wrap mini dress perf for everyday styling! Designed with a stretchy brushed knit fabric, it features a double-lined design at the top for added coverage. The mini-length dress is shaped with a square neckline, thin tank shoulder straps, a faux wrap-front with the cutest tie detail at the waist, and a form-hugging fit to showcase your curves. Pair with slip-on sandals.
Fit & Features
- Stretchy brushed knit fabric, double-lined top
- Square neckline
- Tank straps
- Faux wrap-front with tie detail
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5761
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flawless Beauty Eyelet A-Line Mini Dress
Make every heart flutter in this eyelet mini dress boasting a flirty bust tie and flattering A-line silhouette. Perfect for shower celebrations or brunch!
Fit & Features
- Eyelet knit stretchy fabric, stretchy knit lining
- V-neckline, spaghetti straps
- Bust tie
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6037
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Trend Ribbed Knit Tube Crop Top
Elevate the trends in this ribbed knit tube top perfect for off-duty days! Designed with a trendy strapless neckline with sleek metal hardware. The form-hugging design flatters your figure while the cropped hem adds a touch of sass. Complete the look in high-rise cargo pants.
Fit & Features
- Stretchy ribbed knit fabric
- Metal hardware insert
- Form-hugging
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1920
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Must-Have Tie Back A-Line Mini Dress
A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!
Fit & Features
- Slinky knit fabric lined with stretchy knit
- Open tie-back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5681
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Flattering Crepe A-Line Mini Dress
This crepe cowl neck mini dress flaunts an A-line silhouette with a slit accent and spaghetti straps for a truly stylish look. Feel confident and look amazing in this fashionable, yet comfortable, mini dress that will become your go-to for any occasion! Complete the look in statement stiletto heels and a cropped jacket for dressy to semi-formal occasions!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- A-line silhouette, slit accent
- Mini-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2797
Category Name: Vacation Looks
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beachside Trend Checkered Straw Bucket Hat
From summer beach days to vacays, this checkered straw bucket hat will be your favorite sunny day essential! It features a convenient inner adjustable strap with velcro closure for a perfect snug fit. Complete the look in sandals.
Fit & Features
- Checkered pattern
- Straw material
- Inner adjustable strap with velcro closure
- Bucket hat style
Style Number/Barcode: 07302-1628
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Vibe Ditsy Floral A-Line Midi Dress
Look oh-so-darling at weekend brunch in this ditsy floral A-line midi dress! The sleeveless sweetheart neckline is detailed with a dainty lace trim and tie-front design.
Fit & Features
- Woven fabric
- Ditsy floral print
- Sleeveless sweetheart neckline, dainty lace trim, lace trim spaghetti straps
- Tie-front detail, underbust seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5989
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Good Vibes High Rise Boyfriend Jeans
Bring the good vibes to your casual everyday look with these trendy boyfriend jeans! They feature a high-rise waist, a straight leg, major destructed detailing at the knees, and a relaxed fit. The light wash denim fabric offers minimal stretch. Style these jeans with a cute crop top and clear heels.
Fit & Features
- High-rise waist
- Straight leg
- Destructed detailing at the knees
- Relaxed fit, minimal stretch
- Light wash denim fabric
- Traditional five-pocket and belt loop design
- Hidden zipper and front button closure
- Runs true to size
Style Number/Barcode: 06602-0241
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Floral Chiffon Lace Trim Skater Dress
Charm them all with your pretty flair in this breezy floral chiffon lace trim skater dress! Designed with an airy sheer floral chiffon fabric with a dainty eyelash lace trim, this short dress is the effortlessly chic style you need for parties. The bodice is shaped with a sweetheart neckline with ruching at the bust and adjustable spaghetti straps with ruffled flutter sleeves for a sweet feminine vibe. The fitted waist is accented with an open tie-back design, leading to a flowy skater skirt with an A-line silhouette. Complete the look with hoop earrings and espadrille wedges.
Fit & Features
- Sheer floral chiffon fabric, woven lining with eyelash lace trim, no stretch
- Ruched sweetheart neckline
- Adjustable spaghetti straps with ruffled flutter sleeves
- Open tie-back design
- Lower zipper with hook and eye closure
- A-line fit
- Runs true to size
Style Number/Barcode: 05101-3154
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Vacation Long Sleeve V-Neck Cutout Mini Dress
This V-neck mini dress pairs perfectly with your next vacation or pool party! This playful and stylish dress features long sleeves with flare cuffs, a V-neckline with a hoop insert, and cutout details on the bodice and back. Its bodycon fit and mini-length hem will highlight your curves while you explore exotic destinations or the resort bar! Complete the look with sunnies.
Fit & Features
- Texture knit fabric, sewn-in knit lining, minimal stretch
- V-Neckline with hoop insert
- Cutout bodice and back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5705
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sensational City Girl Strapless Cargo Mini Dress
Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!
Fit & Features
- Cotton-blend woven fabric, minimal stretch
- Strapless straight neckline with belt loop detailing
- Front button closure
- Hidden front zipper closure
- Cargo flap pockets
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5503
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free