Vacation Looks

Loading...

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: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 50s Icon Halter Plunge Neck Skater Romper

    Chanel a popular 50s iconic look in this halter plunge skater romper perfect for themed parties or summer holidays! With a flattering halter neckline and charming tie closure, this romper will create a stunning silhouette. The skater shape and short hem add to its playful appeal. Complete the look with hoop earrings.

    Fit & Features

    • Smooth cotton-blend knit fabric, moderate stretch
    • Halter plunge neckline, tie closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 06503-1138

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, BROWN

    Available Size: S, M

    Product Badge:
    • Sale
  • 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
  • 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: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • 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
  • Casual Staple Ribbed Knit Bandeau Top

    This casual ribbed knit bandeau top is a staple style to have in your closet. Pair with your fave high-rise bottoms or layered under cute tops!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Strapless straight neckline
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07109-000001

    Category Name: Vacation Looks

    Price: $6.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • 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
  • 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
  • Always Trending Strapless Striped Bodycon Mini Dress

    Trend right in this strapless mini dress featuring a twist sweetheart neckline with a keyhole cutout and a flattering bodycon silhouette. The striped knit material hugs your curves making it perfect for pairing with sneakers or sandals. 

    Fit & Features

    • Striped print, stretchy knit material
    • Strapless sweetheart twist neckline
    • Keyhole cutout
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5824

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Short But Sweet Gingham Bow Shorts

    Short but super sweet! These gingham shorts are the cherry on top of a perfect sunny day look featuring a flattering high-rise waist and side bow ties.

    Fit & Features

    • Gingham print, cotton woven fabric
    • High-rise elasticized waist
    • Hidden side pockets
    • Side bow ties
    • Fitted hem
    • Runs true to size

    Style Number/Barcode: 06303-000017

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Luxe Rhinestone Charm Belly Chain

    This dainty rhinestone charm belly chain is dotted with shimmering charms—perfect for layering or letting it shine solo on your next night out.

    Fit & Features

    • Rhinestone charms
    • Dainty chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-000190

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Ready Tropical Knit Halter Crop Top

    This alluring tropical halter crop top will have you ready for a dreamy vacay! The lined stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The crop top is shaped with a sleeveless halter neckline with a sultry V-shaped cutout, tie-back halter straps, ruched side seams to accentuate your curves, and a form-hugging fit for a snatched look. Style with the matching wide-leg pants and hoop earrings.

    Shop Matching Bottoms: Vacay Ready Tropical Knit Wide-Leg Pants

    Fit & Features

    • Abstract tropical print
    • Stretchy lined knit
    • Halter neckline, V-shaped cutout
    • Tie-back spaghetti straps
    • Ruched side seams
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5210

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy-Chic Shell Thong Strap Sandals

    These beachy-chic shell thong strap sandals are a style staple for your summer vacay! Made with faux leather, they feature an almond toe, a trendy thong strap design with sleek oval-shaped shell accents, thin adjustable ankle and heel straps with a buckle closure, and a flat sole for comfortable wear. Pair with a crochet top and denim shorts! 

    Fit & Features

    • Faux leather upper
    • Almond toe
    • Thong strap design
    • Oval shell accents
    • Adjustable ankle and heel straps with buckle closure
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1208

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knit The Beach Striped Strappy Crochet Crop Top

    This striped crochet crop top is all about the beach life! Featuring a square neckline, spaghetti straps, and a strappy open back, this top is perfect for summer fun. Its cropped hem adds a trendy touch. Complete the look in denim shorts.

    Fit & Features

    • Striped pattern, crochet fabric, no stretch
    • Square neckline
    • Spagehtti strap, strappy open back
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2007

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl Next Door Vibes Cropped Tank

    Look like the total girl next door in this basic cropped tank. This staple piece goes with everything from your casual looks or as a layering piece for a dressed-up look. The cropped tank features a sleeveless bodice and bungee spaghetti straps for a secure and comfortable fit. Complete your girl-next-door look with high waist jeans and a pair of sneakers.

    Shop In More Colors: Girl Next Door Cropped Tank

    Fit & Features

    • V-neckline
    • Bungee straps
    • Cropped
    • Knit fabric
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4459

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free