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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STYLE SPOTLIGHT

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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.

Minimalistic Elegance Square Ring Flat Sandals
Indulge this season in these minimalistic faux leather flat sandals for an elegant and chic look! They feature a sleek square toe, a thong toe strap with a chunky square ring decor, and a cushioned footbed for all-day comfort. Complete the look with a trendy handbag.

Fit & Features
- Flat sole
- Thong toe strap, chunky square ring
- Cushioned footbed
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1206

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breezy Nights Crop Crochet Sweater
Embrace effortless style with this crochet sweater perfect for styling over a swimsuit or tank top. This sweater offers a blend of comfort and allure with relaxed long sleeves, a flirty one-shoulder neckline, and a cropped hem.

Fit & Features
- Sheer crochet knit fabric
- One-shoulder neckline
- Relaxed long sleeves
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06005-000048

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: BLACK

Available Size: L
Dreamy Escape Strapless Tropical Midi Dress
Serve chic looks on your dreamy escape in this tropical print midi dress. The stretchy lined knit fabric showcases a detailed tropical print pattern on the figure-flaunting silhouette. The bodice features a strapless elasticized straight-across neckline, leading to a bodycon fit with a mid-length hem. Style with combat booties to add some edge!

Fit & Features
- Stretchy knit fabric with knit lining
- Tropical print
- Strapless elasticized straight neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5539

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Oopsie Daisy Sleeveless A-Line Mini Dress
Oopsie daisy this sleeveless mini dress must've caught you by a sweet surprise! Crafted from a soft brushed knit fabric with an adorable floral print, this dress is a must-have for spring and summer. Features a flattering V-neckline with an adjustable drawstring tie and an A-line silhouette. Complete the look with a denim jacket and sandals for a casual occasion!

Fit & Features
- Floral print, brushed knit fabric lined with knit
- Adjustable drawstring neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5686

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cute Trendsetter Thong Strap Faux Leather Sandals
These cute and trendy faux leather sandals are perf for leveling up your warm-weather looks! Made from a sleek faux leather material, these sandals feature a square-shaped toe with a wide thong strap. The slip-on-and-off design on the flat sole allows for effortless styling. Pair these sandals with an adorable tote bag.

Fit & Features
- Flat sole
- Faux leather upper
- Square toe
- Wide thong strap design
- Slip-on-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1174

Category Name: Vacation Looks

Price: $4.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All About Floral Sweetheart Crepe Skater Dress
Sweet and sassy, this floral skater dress is a must-have for your wardrobe! Featuring a trendy sweetheart neckline and adjustable spaghetti straps, this dress is perfect for any spring or summer occasion. Its skater silhouette and short-length hem will have you twirling all day, while the playful floral print will make you stand out in style! Complete the look with hoop earrings.

Fit & Features
- Floral print
- Stretchy crepe fabric, knit lining at the bust
- Sweetheart neckline
- Adjustable spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3196

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Chic Straw Shoulder Bag
Embrace a boho chic season by styling your fave 'fits with this adorable straw shoulder bag! Crafted with a trendy woven straw design, this bag features a small rectangular shape and a faux leather shoulder strap with sleek metal O-ring accents. Pair with the matching hat and heels!

Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote Bag
Shop Matching Heels: Boho Chic Straw Platform Block Heels

Fit & Features
- Woven straw design
- Small rectangular shape
- Faux leather shoulder strap with metal O-ring accents
- Snap-button closure
- Spacious interior
Style Number/Barcode: 07203-1947

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Slip Into Glam Rhinestone Strap Faux Leather Sandals
Slip into glamour with these sleek rhinestone strap sandals for your next party! Designed with smooth faux leather material, they feature an open square-shaped toe, a wide banded strap embellished with all-over sparkling rhinestones, and a flat sole for comfortable wear. The open back offers effortless on-and-off styling. Pair with a fab rhinestone choker necklace.

Fit & Features
- Faux leather upper
- Open square toe
- Wide banded strap with rhinestones
- Open back, flat sole
- Luxe fit cushioned insole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1156

Category Name: Vacation Looks

Price: $12.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Aviator Babe Cap Sleeve Utility Wide-Leg Jumpsuit
Soar into this utility jumpsuit to take your style to new heights! Perfect for casual outings or travel, this twill-woven jumpsuit offers style and functionality with trendy cap sleeves, a collar neckline, button-down front closures, an adjustable tie-waist belt to snatch your figure, convenient front pockets to keep your things handy, and a flattering wide-leg silhouette. Complete the look in platform sneakers.

Fit & Features
- Twill woven fabric with stretch
- Button-down front closures
- Adjustable tie-waist belt, front pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0824

Category Name: Vacation Looks

Price: $20.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stay Sweet Flutter Sleeve Ditsy Floral Mini Dress
Stay sweet in the cutest ditsy floral mini dress, perfect your for weekend plans! The stretchy brushed knit fabric features an adorable ditsy floral print for the prettiest vibe. The mini-length dress is shaped with a sweetheart neckline with flirty ruching and short flutter sleeves for an effortless look. The bodycon silhouette will flaunt your gorgeous figure. Style with hoop earrings and strappy sandals!

Fit & Features
- Ditsy floral print
- Stretchy brushed knit fabric
- Sweetheart neckline with ruching
- Short flutter sleeves
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5586

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Free Flowing Cutie V-Neck Ruffle Eyelet Maxi Dress
Flattering and breezy come together on this charming eyelet lace maxi dress perfect for spring days and summer cuteness! This dreamy dress features a flattering V-neckline, adjustable spaghetti straps, and charming button accents. The cutout waist and flowy silhouette accentuate your figure, while the tiered ruffled maxi hem adds a whimsy touch. Complete the look in wedge sandals and a floppy hat!

Fit & Features
- Eyelet lace fabric lined with woven fabric
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Cutout waist
- Ruffled maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3286

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Meant To Last Square Toe Block Heel Mules
These faux leather block heel mules are meant to last on rotation from season to season! Designed with a sleek square toe and a wide banded strap, these sandals have a cute block heel with a gold trim detail for some luxe. Complete the look with the matching bag for any occasion!

Shop Matching Shoulder Bag: Made For You Faux Leather Shoulder Bag
Shop Matching Crossbody Bag: Pretty Perfect Floral Strap Crossbody Bag

Fit & Features
- 3" Block heel with gold trim
- Square toe
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4710

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Chic Crossbody Straw Tote Bag
Mini and boho chic, this straw crossbody tote bag was made for fun under the sun! Pack this essential bag for vacations, weekend trips, or a beach day. It features a straw exterior with faux leather trim for a polished look, top handles, a detachable and adjustable crossbody strap to give you multiple ways to wear it, and a spacious interior to hold your things. Complete the look with the matching hat and heels!

Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
Shop Matching Heels: Boho Chic Straw Platform Block Heels

Fit & Features
- Straw material
- Faux leather trim
- Top handles
- Detachable and adjustable crossbody strap
- Zipper closure
- Spacious interior, zipper pocket
Style Number/Barcode: 07203-1946

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreamy Boho Paisley Satin Scarf
Give off dreamy boho vibes with this sleek paisley satin scarf! Designed with a silky satin material with a trendy paisley pattern, this scarf offers multiple styling options. Wear it as a headwrap, a hair tie, or tie it around your neck for a chic accent! Pair with a layered charm necklace.

Fit & Features
- Non-stretch satin material
- Paisley pattern
Style Number/Barcode: 07305-0493

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Talking Sweet One-Shoulder Cutout Eyelet Lace Dress
Dress to impress in this sweet one-shoulder cutout eyelet lace dress guaranteed to turn heads as the lovely bride-to-be or graduate! Made from eyelet lace fabric, this bodycon dress will hug your curves in all the right places. This stunning mini-length dress features a trendy one-shoulder neckline, a flirty puff sleeve, and a sultry side drawstring cutout so you can customize the look. Style this dress with sandals and a tote bag.

Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Drawstring side cut-out
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5715

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
You Love Me Graphic Tank Top
Unapologetically bold and playful, this graphic tank top is a must-have for those who want to make a statement. Featuring a cropped design and eye-catching "You Look Like You Love Me" graphic, this tank top exudes attitude.

Fit & Features
- Stretchy rib knit fabric
- Crew neck
- Racerback design
- "You Look Like You Love Me" graphic script
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000072

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: In Stock

Available Color: WHITE

Available Size: L
Product Badge:
- Sale
Sweetest Allure Strapless Floral Eyelet Knit Midi Dress
Give off the sweetest allure this summer season in this floral eyelet knit midi dress! The stretchy sheer eyelet knit fabric is detailed with an adorable ditsy floral print and includes a full knit lining for coverage. The mid-length dress features a strapless straight-across elasticized neckline and a bodycon silhouette to highlight your gorgeous figure. Style with espadrille wedges for weekend brunch!

Fit & Features
- Stretchy sheer eyelet knit fabric, full knit lining
- Ditsy floral print
- Strapless straight elasticized neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5488

Category Name: Vacation Looks

Price: $5.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Charming Style Puff Sleeve Chiffon Skater Dress
Create the sweetest charming style for your spring and summer parties in this chiffon skater dress! The airy sheer chiffon fabric offers that breezy lightweight feel and includes a stretchy knit lining for coverage. The short dress features a ruched square neckline, adorable short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette for a flirty vibe with a ruffled hem. Pair with sneakers for a cute and casual look!

Fit & Features
- Sheer chiffon fabric with stretchy knit lining
- Ruched square neckline
- Short puff sleeves with elasticized hems
- High waist seams, back zipper with hook and eye closure
- Skater silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3056

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sheer Fun Off-The-Shoulder Crop Chiffon Blouse
You'll have the most fun in this cute chiffon crop blouse on a date night or evening out! The breezy sheer peasant long sleeves and off-the-shoulder neckline add a flirty touch, while the adjustable front ruched drawstring allows for a personalized fit. Complete the look in a sleek faux leather midi skirt and pointy toe heels for a chic allure!

Fit & Features
- Chiffon woven fabric
- Off-the-shoulder
- Front ruched drawstring
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2355

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Eye-Catching Vibes Cut Out Bodycon Mini Dress
Keep every eye on you in this bodycon mini dress for flawless vibes at parties! Made from a brushed soft knit double-lined fabric, this dress offers ultimate comfort and style. Featuring a square neckline, spaghetti straps, and a bodycon fit, this dress will enhance your curves and make you stand out. The side cut out and ruched seams add an edgy touch, while the mini-length hem flaunts your figure. Complete the look in sandals and earrings.

Fit & Features
- Brushed knit soft double-lined fabric, stretchy
- Spagehtti straps
- Side cut out, side ruched seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5640

Category Name: Vacation Looks

Price: $19.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Baby Got Open Back Poplin Woven Mini Dress
Get ready to turn heads in this open back poplin woven mini dress! This bodycon mini dress features a square neckline, spaghetti tie straps, and a spaghetti tie back strap for a playful twist along the sultry open back. Made with a lightweight poplin woven fabric, this dress is perfect for hot days and even hotter nights! Complete the look in heeled sandals and a purse.

Fit & Features
- Poplin woven fabric lined with stretchy knit
- Spagehtti tie straps and back strap
- Open back
- Hidden side zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5760

Category Name: Vacation Looks

Price: $5.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Getaway Chic Marble Buckle Raffia Belt
Define your silhouette in this chic raffia belt perfect for inspiring your next getaway! It features a marble print buckle closure and an adjustable fit on raffia material. Complete the look in clear stiletto mules.

Fit & Features
- Marble print buckle closure
- Adjustable fit
- Raffia material
Style Number/Barcode: 07301-0857

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Chic Tiered Floppy Straw Hat
Floppy and boho chic, this straw hat was made for fun under the sun! Pack this essential hat for vacations, weekend trips, or a beach day. It features a unique tiered design along the floppy brim that shades from the sun and adjustable interior strings so you can get a snug fit. Complete the look with the matching bag and heels!

Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote Bag
Shop Matching Heels: Boho Chic Straw Platform Block Heels

Fit & Features
- Straw material
- Tiered design
- Floppy brim
- Adjustable interior strings for a snug fit
Style Number/Barcode: 07302-1555

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cutest Style Halter Knit Crop Top
You always have the cutest style, so this halter knit crop top is the perfect addition to your summer closet! The knit fabric adds a comfy cozy feel to the trendy silhouette. The top has a sleeveless high halter neckline and a front V-shaped hanky cropped hem. Pair with distressed jeans for your casual weekend plans!

Fit & Features
- Knit fabric, minimal stretch
- Sleeveless high halter neckline
- V-shaped hanky cropped hem
- Fitted
- Runs true to size
Style Number/Barcode: 06005-1894

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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