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 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.

Living My Best Life Satin Tie-Dye Tube Top
Ideal for sunny days, living your best life. This satin tie-dye tube top elevates your look with a sleek strapless neckline and pointed crop hem that flaunts your figure.

Fit & Features
- Tie-dye print, satin fabric, stretchy smocked back
- Strapless tube neckline
- Pointed crop hem
- Runs true to size
Style Number/Barcode: 06003-000042

Category Name: Vacation Looks

Price: $26.90

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Day Dream High-Rise Wide Leg Pants
Look like a tropical day dream in these high-rise pants while on vacation! The elasticized waistband ensures a comfortable fit, while the wide-leg silhouette and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching top and skirt.

Shop Matching Top: Tropical Day Dream Tie-Front Crop Top
Shop Matching Skirt: Tropical Day Dream High-Rise Wrap Mini Skirt

Fit & Features
- Tropical print, stretchy knit fabric
- High-rise elasticized waistband
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2469

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Classic High-Rise Destructed Cut-Off Denim Shorts
Create the cutest summer 'fits with this classic pair of destructed cut-off denim shorts! Detailed with trendy distressed detailing on the medium-wash denim fabric, these jean shorts are the perfect casual staple. They feature a flattering high-rise waist, a fitted cut-off hem, a traditional five-pocket and belt loop design, and a secure front button and hidden zipper closure. Style with a crop top and strappy sandals.

Fit & Features
- Distressed denim fabric, moderate stretch
- High waist
- Fitted cut-off hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Runs true to size
Style Number/Barcode: 06603-0389

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Flutter Sleeve Tie-Front Eyelet Crop Top
Capture hearts with this flirty flutter sleeve tie-front crop top! Designed with a lightweight woven fabric, it features a ruffled V-neckline with short flutter sleeves, a tie-front design for a stylishly cinched silhouette, a partial low back, and a cropped hem with an adorable eyelet trim. Complete the look with denim shorts and sandals.

Fit & Features
- Textured woven fabric, sewn-in knit lining
- Ruffled V-neckline
- Short flutter sleeves
- Tie-front cinched silhouette
- Partial low back
- Cropped hem with eyelet trim
- Runs true to size
Style Number/Barcode: 06003-2581

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hello Summer Triangle Bikini Top
Say hello to summer in this trendy bikini top featuring triangle-shaped cups with removable padding and dual spaghetti strap ties that let you customize the style. Pair with the matching bikini bottoms for a pool party.

Shop Matching Bottoms: Hello Summer V-Cut Bikini Bottoms

Fit & Features
- Nylon-blend fabric, high stretch
- Triangle design
- Removable padding
- Dual tie-back halter straps
- Lower tie-back straps
- Runs true to size
Style Number/Barcode: 07104-000008

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Exotic Vibes Strapless Tie-Front Tropical Romper
You'll be looking exotic and beautiful in this tropical romper on vacation or by the pool! Featuring a flattering strapless sweetheart neckline and tie-front bust, this romper also offers a comfortable and stylish fit with its stretchy smocked back with cutout and a flowy short-length hem. Complete the look with a layered necklace and strappy sandals.

Fit & Features
- Tropical print, woven fabric lined with stretchy knit
- Strapless sweetheart neckline
- Tie-front bust
- Smocked back with cutout
- Flowy short-length hem
- Runs true to size
Style Number/Barcode: 06403-0427

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Talker Strappy Back Halter Skater Mini Dress
Sweeten any room with your vibe in this halter skater dress, which flaunts a strappy open back that turns heads with every wear!

Fit & Features
- Woven fabric, stretchy knit lining
- Halter V-neckline with spaghetti strap tie
- Open back with tie-back detail
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6029

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sway With The Palm Print Mesh Duster
Sway with the breeze in this palm print mesh duster to layer over your chic vacation or pool party look! The duster has fitted long sleeves and an open front design giving everyone a peek at your cute self, and a flowy longline hem. Complete the look in flat sandals and sunnies!

Fit & Features
- Palm print
- Stretchy sheer mesh fabric
- Long fitted sleeves
- Flowy longline hem
- Runs true to size
Style Number/Barcode: 06202-0445

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sky Gazing Moon Star Chain Belt
Adorn yourself with celestial style with this moon star chain belt perfect for skygazers and dreamers! Featuring charming moon and star charms and a secure lobster clasp closure, this chain belt adds a touch of magic to any outfit. Complete the look in a trendy denim romper for a festival, concert, or night at the fair!

Fit & Features
- Moon and star charms
- Chain belt
- Lobster clasp closure
Style Number/Barcode: 07301-1109

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Safari Babe Zebra Rhinestone Faux Suede Cowboy Hat
Look and feel like a total safari babe in this zebra cowboy hat! This hat is made from soft faux suede and features a curved wide brim to help protect from the sun and an inner adjustable string for a snug fit. The rhinestone embellished trim and cord with adjustable toggle add a touch of glamorous detail. Complete the look in a flirty romper and boots for a jungle adventure!

Fit & Features
- Zebra print
- Curved wide brim
- Rhinestone embellished trim and cord with adjustable toggle
- Inner adjustable strings
- Faux suede material
Style Number/Barcode: 07302-1638

Category Name: Vacation Looks

Price: $4.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Playfully Perfect High Rise Slit Mini Denim Skirt
This mini denim skirt is playfully perfect for every casual social plan on your radar! With a high-rise waist and curve-enhancing seams along the bodycon silhouette, this skirt flatters your figure. Plus, the dual front slits add a flirty touch while the mini-length hem keeps things playful. Complete the look in a cute tee and sneakers.

Fit & Features
- Medium-wash denim fabric, no stretch
- High-rise waist
- Bodycon silhouette
- Five-pocket styling, front button closure
- Hidden zipper closure
- Runs true to size
Style Number/Barcode: 06601-0197

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Under The Sun Tropical Flower Hair Comb
Enjoy the island under the sun adorning your tresses with this beautiful tropical flower hair comb! Complete the look in a matching set and sandals.

Fit & Features
- Tropical flower hair comb
Style Number/Barcode: 07006-0469

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fun Favorite High Rise Distressed Denim Shorts
Grab your bestie and throw on these denim shorts for a fun summer adventure! Made from a medium wash fabric with a cool vintage-inspired color fading, these jean shorts will be essential all season. They feature a flattering high-rise waist, distressed accents for a major trend factor, and an edgy cut-off hem. Complete the look in a cute crop top and sandals!

Fit & Features
- Medium wash denim, color fading effect
- High rise waist
- Distressed accents, cut off hem
- Front button and hidden zipper closure
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-0395

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top
Sweet and flirty, this flutter-sleeve floral tie-front top will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The top features a V-neckline with a tie-front design, short flutter sleeves for a feminine touch, and a cropped hem with a relaxed fit. Style with the matching mini skirt for a day date!

Shop Matching Bottoms: Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt

Fit & Features
- Ditsy floral printed knit fabric, moderate stretch
- V-neckline with tie-front design
- Short flutter sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06202-0464

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breezy Look Ruffled Cutout Woven Maxi Dress
Create a breezy-chic look with this woven maxi dress that will prove to be a summer staple! Designed with a lightweight woven fabric accented with ruffled trims, the long dress features a sleeveless square neckline with a keyhole cutout and tie-front detail, adjustable spaghetti straps for a customized fit, and dual cutouts at the stretchy smocked waist that lead to an open lower back. The tiered flowy A-line silhouette will give you an effortlessly pretty look. Style with strappy sandals.

Fit & Features
- Woven fabric, ruffled trims, short knit stretchy lining
- Square neckline, keyhole cutout with tie-front
- Adjustable spaghetti straps
- Stretchy smocked waist
- Dual cutouts leading to open lower back
- Tiered flowy A-line fit
- Runs true to size
Style Number/Barcode: 05102-5729

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Dreams Halter V-Neck Boho Chiffon Maxi Dress
Summer dreams are made of this boho chiffon maxi dress perfect for your vacation or weekend getaway! The halter V-neckline and spaghetti strap tassel ties provide an effortlessly chic touch, while the stretchy smocked bodice and hidden side pockets offer convenience. The flowy ruffled silhouette adds a touch of romance! Complete the look in sandals and a bracelet.

Fit & Features
- Bohemian print, chiffon fabric with woven lining, no stretch
- Halter V-neckline
- Spaghetti strap tassel ties
- Stretchy smocked bodice
- Hidden side pockets
- Flowy ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5777

Category Name: Vacation Looks

Price: $6.97 $64.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feel The Vibes Halter V-Neck Crop Top
Get ready to feel the vibes of this elevated basic halter V-neck crop top! It's perfect for styling with any bottoms.

Fit & Features
- Smooth knit, cotton-blend, stretchy fabric
- Halter V-neck
- Crop hem
- Runs true to size
Style Number/Barcode: 06002-000206

Category Name: Vacation Looks

Price: $24.90

Availability: In Stock

Available Color: GREEN, OFF, WHITE, BLACK, BROWN

Available Size: XS, S, M, L
Spring Breeze Sweetheart Tie Eyelet Crop Top
Spring into the new season in this eyelet crop top for vacations or weekend fun! Featuring a playful sweetheart neckline and delicate spaghetti straps, this top will keep you feeling cool and confident. The tie front adds a touch of charm, while the cropped hem and eyelet lace fabric offer a romantic and airy look. Complete the look with the matching bottoms.

Shop Matching Bottoms: Spring Breeze Ruffled Eyelet Maxi Skirt

Fit & Features
- Eyelet lace fabric, slight stretch
- Spaghetti straps
- Tie front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5282

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On Trend Layered Bead Necklace
Achieve an on trend look with this layered necklace featuring colored beads that give your outfit a refreshing update! Complete the look with sandals.

Fit & Features
- Layered design
- Colored beads
- Lobster clasp closure
Style Number/Barcode: 07002-1861

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hey Shorty High-Rise Cut Off Denim Shorts
Hey, shorty looking cute in these high-rise denim shorts! Perfect for any spring or summer plans, these shorts fit just the way you want and flatter from every angle. The high-rise waist and form-hugging fit hug your figure, while the distressed accents and cut-off hem add a touch of edgy style. Complete the look in a flirty crop top.

Fit & Features
- Denim fabric with stretch
- High-rise waist, hidden front button and zipper closure
- Distressed accents, five-pocket styling
- Cut off hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0378

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Alluring Vacay High Slit Tropical Mesh Midi Dress
Dare to allure on your next vacay in this sultry high slit tropical midi dress! The airy-lined mesh fabric is detailed with a bold all-over tropical palm leaf print to bring those dreamy destination vibes to your look. The mid-length dress features a sleeveless square neckline with pleating, spaghetti straps that lead to an open cross-back strappy design, a high-cut side slit to show off some leg, and a slim-fit silhouette to flaunt your figure. Style with hoop earrings and sandals for a beachy-chic outfit.

Fit & Features
- Tropical print
- Stretchy mesh fabric with knit lining
- Square neckline
- Spaghetti straps, open cross-back strappy design
- High side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5688

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wanderlust Mode Wide-Leg Pants
Crush your style game in these wide-leg pants. With a smooth knit and flared hem, these pants bring effortless chic to your every move. Perfect for your next adventure!

Shop Matching Top: Wanderlust Mode Cutout Tube Top

Fit & Features
- Smooth knit fabrication with stretchy knit lining
- Mid-rise waist
- Straight-leg fit
- Flared wide-leg hem
- Pants in size small have an 11" front rise with a 28" inseam
- Runs true to size
Style Number/Barcode: 06502-2569

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stars Align Filigree Earrings
The stars have aligned and these earrings belong in your jewelry box. They feature a metal filigree design and a rubber-back stopper for a secure fit. Complete the look in a sleek bodycon dress.

Fit & Features
- Metal filigree design
- Rubber-back stopper
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1264

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling Fun Cuffed Denim Mini Skirt
Forever classic with a fun touch, this denim mini skirt boasts a flattering bodycon fit and a unique cuffed hem. Pair with a cute top for a farmer's market!

Fit & Features
- Denim fabric
- High-rise waist, belt loops
- Front button and hidden zipper closure
- Dual front and back pockets
- Mini-length cuffed hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06601-000002

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials