Vacation Looks
Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.
HomeVacation Looks

Vacation Looks
Product Recommendations
STYLE SPOTLIGHT
Get Eye-Catching Sandals For Women
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.
-
Effortless Era Woven A-Line Midi Dress
Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.
Fit & Features
- Poplin smooth cotton woven fabric with full-length woven lining
- Sleeveless square neckline, adjustable spaghetti straps
- Stretchy smocked bodice
- V-shaped waist
- Pleating, hidden side pockets
- Midi-length flowy A-line silhouette, high side slit
- Runs true to size
Style Number/Barcode: 05102-000001
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cute Classic Fold-Over Ribbed Knit Beanie
This cute classic ribbed knit beanie is a winter must-have! It features a thick ribbed knit material with a fold-over design and offers moderate stretch. Style this adorable beanie with a fuzzy faux sherpa jacket.
Fit & Features
- Thick ribbed knit material
- Fold-over design
- Moderate stretch
Style Number/Barcode: 07302-1514
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Effortless Perfection Bodycon Striped Mini Dress
With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!
Fit & Features
- Striped pattern, texture knit fabric, moderate stretch
- Spaghetti straps
- Square neckline with twist
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5675
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cutest Babe Button Up Linen Vest
A sleek fit with tailored details, this sleeveless linen vest is essential for spring-to-summer wear! The vest is designed with a flattering V-neckline, button-up front closures, and a curved cropped hem to flaunt your figure. Complete the look with the matching pants.
Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants
Fit & Features
- Lined linen fabric
- Button up front closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1737
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Beachy Babe Tie-Back Crochet Mini Dress
Channel a beachy babe vibe in this trendy crochet mini dress! Designed with a sheer crochet fabric with a boho-inspired woven design, the short dress includes a stretchy knit lining for coverage. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, an adorable tie-back design, a flirty lower back cutout that peaks out on both sides, and a form-hugging fit to flaunt your figure. Style with espadrille sandals.
Fit & Features
- Crochet fabric with woven design, stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Tie back straps, back cutout
- Hidden side zipper with hook and eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5780
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Summer Icon Striped Crochet Halter Top
You'll be a cool summer icon in this striped crochet crop top featuring a plunging V-neckline with tie-back halter straps and a fitted, cropped hem. Style with cutoff denim shorts!
Fit & Features
- Crochet knit fabric, moderate stretch
- Striped pattern
- Sleeveless plunge V-neckline
- Tie-back halter straps, partially open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06005-000070
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
-
Bri High-Rise Flare Jeans by Windsor Denim
Keep your casual everyday 'fits trendy with the Bri high-rise flare jeans. This pair by Windsor Denim features a fitted high-rise waist, destructed detailing at the knees, and a fab flare hem. The denim fabric offers a moderate stretch for comfortable wear. Style with a bodysuit and mules.
Fit & Features
- High-rise waist
- Destructed detailing at the knees
- Fitted silhouette, flare hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0354
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
All This Love Cowl Halter Crop Top
A sweet crop top with a sultry open back and cowl halter neckline that dresses up your favorite jeans.
Fit & Features
- Smooth knit stretchy fabric
- Cowl halter neckline, spaghetti strap tie
- Open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000087
Category Name: Vacation Looks
Price: $22.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Instant Fave Disty Floral Short Sleeve Midi Dress
This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.
Fit & Features
- Crew neckline, short sleeves
- Small back keyhole cutout, button closure
- Larger lower back cutout, high waist seam
- Midi-length hem, front slit, form-hugging fit
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5184
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Love's In The Air Floral Chiffon A-Line Dress
Slip into the romantic vibes of this floral chiffon mini dress for day dates to shower celebrations! The dress flaunts a pretty corset bodice and lace-up back that turns heads, while the A-line silhouette flatters your figure.
Fit & Features
- Dainty floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05101-4046
Category Name: Vacation Looks
Price: $9.97
Availability: Out of Stock
Product Badge:- Ships Free
-
Chic Touch Faux Wool Beret
This beret will add a chic touch to all of your 'fits this season! It features a classic beret design and is composed of a faux wool material. Style with an oversized blazer and ankle booties for a city trip!
Fit & Features
- Classic beret design
- Faux wool material
- Moderate stretch
Style Number/Barcode: 07302-1486
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Serving Curves Keyhole Maxi Dress
Serving curves and confidence—this dress eats every time. The keyhole cutout and body-hugging silhouette? A certified head-turner for nights that don’t end early.
Fit & Features
- Stretchy textured knit fabric
- Scoop neckline with spaghetti straps
- Front keyhole cutout at bust
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000166
Category Name: Vacation Looks
Price: $35.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M
-
Effortless Influence Strapless Bodycon Midi Dress
Achieve a stylish rep in this strapless midi dress wherever you go! With a flattering bodycon fit and trendy stone metal insert, this dress will enhance your natural silhouette and captivate any room you enter.
Fit & Features
- Stretchy knit fabric
- Strapless neckline, stone metal insert
- bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000062
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Softest Style Plaid Frayed Scarf
This plaid frayed scarf will be the softest style in your lineup! Perfect for wearing around your neck or shoulders, the styling possibilities are endless. Complete the look in cute boots.
Fit & Features
- Plaid pattern
- Frayed edge trim
- Ultra-soft knit material
Style Number/Barcode: 07305-0459
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Coastal Escape Cropped Halter Top
Shop Matching Bottoms: Coastal Escape High Rise Ruched Midi Skirt
Fit & Features
- Smooth knit fabrication
- Sleeveless halter neckline
- Halter neck ties
- Cutouts
- Beaded detailing
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5672
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cold Weather Luxe Faux Fur Trim Gloves
Enter into the cold season with luxe style with these faux fur gloves! They feature a fitted design made from soft faux suede material with chic faux fur cuffs. Complete your cute cold-weather 'fit with a rhinestone-embellished beanie!
Fit & Features
- Fitted design
- Faux suede fabric
- Faux fur cuffs
Style Number/Barcode: 07304-0047
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Feelin' Bold Floral Mesh Strapless Maxi Dress
Be a bold babe in this airy mesh maxi dress designed with a large floral print pattern to turn heads. Featuring ruching at the bust, a high-cut side slit, and a form-hugging silhouette, style with wedges for a sunset dinner.
Fit & Features
- Sheer mesh fabric with full-length brushed knit lining, high stretch
- Large floral print
- Strapless straight-across neckline
- Ruched bust
- Thigh-high side slit
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000098
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: CORAL
Available Size: XS
Product Badge:- Sale
-
My Lane Corduroy Faux Sherpa Collar Crop Jacket
Take a walk down style lane in this corduroy crop jacket essential for the chilly season ahead! It features long sleeves with button cuffs, a faux sherpa collar, button-down front and flap pockets, and a back elasticized cinch hem. Layer over a basic top and currently trending cargo pants.
Fit & Features
- Long sleeves, button cuffs
- Faux sherpa collar
- Button down front, flap pockets
- Cropped hem
- Back elasticized cinch hem
- Corduroy fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1690
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cute But Chill A-Line Mini Dress
Looks like a serve, feels like a chill day 'fit. This nylon mini dress comes through with a flattering silhouette and hidden shorts, so you can dance, lounge, or do your thing without a second thought.
Fit & Features
- Smooth nylon fabric, moderate stretch
- Sleeveless square neckline
- Spaghetti straps
- Short front slit
- Mini-length hem, hidden shorts
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000031
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
-
Sweet Like Summer Crochet Bralette Top
Sweet like summer, this crochet bralette top was made to flirt. With a plunging V-neck, scalloped trim, and open tie-back design, it's your new go-to for coastal vibes. Style with the matching maxi skirt.
Shop Matching Bottoms: Sweet Like Summer Crochet Maxi Skirt
Fit & Features
- Crochet knit fabric, moderate stretch
- Sleeveless plunge V-neckline
- Tank shoulder straps
- Scalloped trim
- Open back, tie-back spaghetti straps
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000052
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Such A Daydream Chiffon Crop Top
You'll look like such a daydream in this airy chiffon crop top! It features a subtle sweetheart neckline, a ruched bust, long sheer bishop sleeves, a cropped hem with a wrap-front detail, and a stylish tie-back design. Complete the look with cute denim and clear mules.
Fit & Features
- Sheer chiffon fabric, front knit lining, minimal stretch
- Sweetheart neckline
- Ruched bust
- Long sheer bishop sleeves, elastic cinched hems
- Cropped hem, wrap-front detail
- Tie-back design
- Runs true to size
Style Number/Barcode: 06003-2301
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
On Repeat Flat Over-The-Knee Boots
These must-have flat over-the-knee boots will be styled on repeat all season long. They feature a fitted over-the-knee design, an inner zipper closure that runs down the length of the boot, an almond-shaped toe, and a flat sole with a short block heel. The boots have a trendy design of sleek faux leather at the front with smooth spandex at the back. Pair with a sweater dress for such a chic winter look.
Fit & Features
- Fitted over-the-knee design
- Complete inner zipper closure
- Almond toe
- Flat sole, short block heel
- Half faux leather material
- Half lycra material
- Runs true to size
Style Number/Barcode: 07402-0980
Category Name: Vacation Looks
Price: $11.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Gorgeous Getaway Tropical Print Crop Top
This alluring tropical print crop top will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a sleeveless plunging V-neckline, halter spaghetti straps, a tie-front design under the bust, and a cropped, ruffled, babydoll hem with a flowy fit. Style with the matching maxi skirt for your next destination vacay!
Shop Matching Bottoms: Gorgeous Getaway Tropical Print Maxi Skirt
Fit & Features
- Sleeveless plunging V-neckline
- Halter spaghetti straps
- Tie-front design
- Cropped, ruffled, babydoll hem, flowy fit
- Tropical print
- Sheer mesh fabric, knit lining at the bust, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-5074
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
-
Bohemian Babe Knit Cutout Tube Top
Channel a boho babe vibe in this sweater knit tube top featuring a strapless straight neckline, dual bust cutouts with a beaded trim, and a front slit accent. Style with the matching mini skirt for a chic and seamless look!
Shop Matching Bottoms: Bohemian Babe Knit High-Rise Mini Skirt
Fit & Features
- Sweater knit fabric, ribbed hems, high stretch
- Strapless straight-across neckline
- Dual bust cutouts, beaded trim
- Front slit design
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06005-000031
Category Name: Vacation Looks
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free