Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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.

  • Always A Vibe Basic Knit Tank Top

    This basic tank top is always a vibe! With a sleek square neckline and form-hugging fit, this top is essential for creating cute fits'.

    Fit & Features

    • Stretchy knit fabric
    • Square neckline
    • Wide shoulder straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-000027

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweeten Up Straw Block Heels

    Sweeten up any look in these heels adorned with a unique straw block heel and trendy crisscross straps. Style with a sundress for any daytime outings!

    Fit & Features

    • 3" Straw block heel
    • Square toe
    • Crisscross straps
    • Adjustable ankle strap, buckle closure
    • Faux leather upper material
    • Runs true to size

    Style Number/Barcode: 07401-000216

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: 5.5, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • All Time Favorite Strappy Metallic Flat Sandals

    Discover your new favorite pair of metallic sandals! They feature a chic square toe and a strappy design that will elevate any outfit. And with their flat sole and metallic faux leather material, they provide a chic and comfortable style. Complete the look with a tote purse.

    Fit & Features

    • Square toe
    • Flat sole
    • Strappy design
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1084

    Category Name: Vacation Looks

    Price: $8.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paisley and Playful Halter Skater Dress

    Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline, spaghetti strap tie
    • Stretchy smocked bust
    • Open tie-back detail
    • Flowy skater silhouette
    • Ruffled trim short hem
    • Runs true to size

    Style Number/Barcode: 05102-000065

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Stylish In The Chill Puffer Jacket

    Keep stylish through the chill in this quilted puffer jacket featuring long sleeves with buttoned cuffs, a collar neckline, snap-button down front closures, flap pockets, and a cropped hem. The jacket is designed with thin insulation to help keep you comfortable and protected from the elements. Style over a long sleeve top with woven joggers.

    Fit & Features

    • Long sleeves, buttoned cuffs, collar neckline
    • Snap-button down front closures
    • Flap pockets
    • Cropped hem
    • Quilted thin puffer woven fabric
    • Insulated and lined
    • Fits true to size

    Style Number/Barcode: 06201-0317

    Category Name: Vacation Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Distressed High Waist Cut-Off Denim Shorts

    These trendy distressed high waist cut-off denim shorts are a summer closet staple! Made with a stretchy cotton-blend denim fabric, they feature a flattering high-rise waist, a fitted silhouette, distressed detailing, and a frayed cut-off hem for an edgy vibe. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jean shorts with a crop top and sneakers.

    Fit & Features

    • Cotton-blend denim fabric, moderate stretch
    • High waist
    • Fitted
    • Distressing, frayed cut-off hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Runs true to size

    Style Number/Barcode: 06603-0377

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serve Looks Square Sunglasses

    Serve nothing but cute looks in these square sunglasses for UV protection and stylish flair!

    Fit & Features

    • Square frames
    • Tinted colored lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000015

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetly Sheer Lace Tie Front Crop Top

    A little angel, a little trouble—this lace crop is your new fave layering piece. Style it over a bralette or solo for that effortlessly flirty, carefree vibe!

    Fit & Features

    • Sheer lace fabric
    • Long sleeves with flare cuffs
    • Tie front
    • Ultra-cropped hem
    • Bra not included
    • Runs true to size

    Style Number/Barcode: 06204-000021

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: M, L

  • Bold Babe Strapless Lace-Up Striped Crop Top

    Level up your summer 'fits like the bold babe you are with this strapless lace-up crop top! Made with a striped ribbed knit fabric, it offers plenty of stretch. The tube top features a strapless straight-across neckline, a trendy lace-up front with an alluring cutout design and tie closure, and a cropped hem with a form-hugging fit for that snatched look. Style with wide-leg pants for a chic vibe.

    Fit & Features

    • Stretchy striped ribbed knit fabric
    • Strapless straight neckline
    • Lace-up front with tie closure
    • Cropped
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06002-1867

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss Jetsetter High-Rise Print Mini Skort

    Whether you're jet-setting to your next adventure, meeting friends for brunch, or creating the perfect vacation look, this printed mini skort is essential for looking cute on the go! Shop the matching top to complete the look.

    Shop Matching Top: Miss Jetsetter Halter Tie-Back Print Crop Top

    Fit & Features

    • Printed design, woven fabric, stretchy knit shorts lining
    • High-rise waist, side zipper and hook-eye closure
    • Skirt overlay with side tie
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06303-000021

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Beauty On Vacay Cutout Abstract Maxi Dress

    From seaside dinners to dancing under the moonlight, this abstract print maxi dress will have you looking like a beauty on the island! It features delicate spaghetti straps, a sweetheart neckline with an O-ring bust insert, a cutout bodice to reveal some skin, and a flattering bodycon silhouette and maxi-length hem. Complete the look with strappy wedges.

    Fit & Features

    • Abstract print, knit fabric, short knit lining
    • Spaghetti straps
    • Sweetheart neckline
    • O-ring bust insert, cutout
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5584

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eyes on You Abstract Print Cutout Mini Dress

    You didn’t just enter the room—you owned it. With a bold cutout and curve-hugging fit, this iconic abstract print mini dress is your go-to for nights out where the vibe is flirty and fearless.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract print
    • Sleeveless sweetheart neckline, padded bra cups
    • Bust cutout with lattice design, large waist cutout
    • Adjustable spaghetti straps
    • Ruching, mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000288

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Keep It Light High Rise Linen Palazzo Pants

    Keep it light and effortless in these high-rise linen palazzo pants for a day spent under the sun! With a high-rise waist and side pockets, these pants offer both a flattering fit and convenience. The palazzo wide-leg silhouette keeps you comfortable, while the linen fabric elevates the look. Style with the matching top.

    Shop Matching Top: Keep It Light Sleeveless Linen Corset Top

    Fit & Features

    • Linen woven fabric, no stretch
    • High-rise waist, stretchy smocked back waistband
    • Pockets
    • Palazzo wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0815

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Never Blend In Butterfly Chain Necklace

    Never blend in but stand out in this butterfly chain necklace secured with a lobster clasp closure. Complete the look in high heels for a dressy occasion.

    Fit & Features

    • Butterfly charms
    • Chain link
    • Lobster clasp closure

    Style Number/Barcode: 07002-1864

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie You Down Mid-Rise Lace-Up Denim Shorts

    Step into trendy fashion in these mid-rise denim shorts! The mid-rise waist and form-hugging fit accentuate your curves, while the front lace-up adds a touch of edgy style.

    Fit & Features

    • Light wash denim fabric, slight stretch
    • Mid-rise waist, front lace-up placket
    • Four-pocket styling
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-000004

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: XS, S, M, L, XL

  • Next Chapter High-Rise Carpenter Denim Shorts

    Write your next stylish chapter in these high-rise denim shorts! With a high-rise waist and form-hugging fit, these shorts accentuate your curves while providing comfort. Plus, the bottom side strap and mini pocket add a unique touch to the medium-wash denim fabric. Complete the look in a graphic tee for casual plans!

    Fit & Features

    • Medium wash denim, slight stretch
    • High rise waist
    • Form-hugging fit
    • Bottom side strap and mini pocket accent
    • Front button and hidden zipper closure
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-0368

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun Chaser Woven Raffia Hoop Earrings

    Vacay mode: fully activated. These woven raffia hoop earrings mix chill island vibes with bold hoop energy—perfect for beach brunch or rooftop golden hour.

    Fit & Features

    • Wide open hoop silhouette
    • Woven raffia and metal blend design
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000029

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Breezy Energy Tie Front Long Sleeve Linen Top

    This linen crop top boasts breezy energy for effortless summer styling! Featuring stylish bell sleeves and a trendy tie-front design, this top will elevate your fashion game. The cropped hem adds a modern touch. Complete the look in a denim mini skirt and sandals.

    Fit & Features

    • Linen blend fabric, no stretch
    • Bell long sleeves
    • Tie-front design
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1760

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Watch Me Bloom Off-The-Shoulder Floral Midi Dress

    Be the talk of any garden party in this floral midi dress! The off-the-shoulder neckline exudes femininity, while the cutout waist shows some skin. The flowy midi-length silhouette and front slit offer a trendy allure. Complete the look in lace-up heels and earrings.

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Off-the-shoulder neckline
    • Cutout waist
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3414

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hot Cowgirl Summer Trucker Hat

    Embody the country vibes in this trucker hat all season! It features a classic curved wide brim, an embroidered script that reads "Hot Cowgirl Summer" and a mesh back with adjustable snap-back closures. Complete the look in a denim jumpsuit.

    Fit & Features

    • Curved wide brim
    • Embroidered script reads "Hot Cowgirl Summer"
    • Mesh back with adjustable snap-back closures

    Style Number/Barcode: 07302-1649

    Category Name: Vacation Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Fit To Bloom Scoop Neck Ditsy Floral Midi Dress

    Sweet summer events are calling and this ditsy floral midi dress is here to make you look cute! Adjustable spaghetti straps and a drawstring scoop neckline provide versatile style, while the form-hugging fit and side slit add a touch of sass. Complete the look in high heels.

    Fit & Features

    • Ditsy floral print, bust lining, knit fabric, moderate stretch
    • Spaghetti straps
    • Drawstring adjustable scoop neckline, bust tie
    • Form-hugging fit
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5774

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off To Paradise Tie-Front Crop Top

    A trending abstract crop top designed with flowy short sleeves and a tie-front design that flaunts your figure on vacay! Pair with the matching pants.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Short sleeves
    • V-neckline
    • Tie-front design
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Pants: Off To Paradise Wide-Leg Abstract Pants

    Style Number/Barcode: 06202-000002

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Daily Cute Vibe Twist V-Neck Crop Top

    Always cute every day, this seamless crop top is perfect for creating alluring looks! Made with seamless rib knit fabric, this crop top is not only stylish but also comfortable. The spaghetti straps and V-neckline provide a sleek and sexy silhouette, while the twist bust adds a touch of flirtiness to the cropped hem that shows off your curves. Complete the look in best-selling bottoms and heels.

    Fit & Features

    • Seamless rib knit fabric, double-lined, moderate stretch
    • Spaghetti straps
    • V-neckline
    • Twist bust
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 07109-0402

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale