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.

All-Day Slay Oversized Cat-Eye Sunglasses
Show off an all-day slay in these sleek cat-eye sunglasses! They feature an oversized cat-eye design with a thin metal frame, sassy leopard-printed arms, and tinted lenses. Style these chic shades with hoop earrings.

Fit & Features
- Oversized cat-eye design
- Thin metal frame
- Leopard-printed arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1066

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
City In Style Rhinestone Trim Sunglasses
Stroll the city in these stylish sunglasses for a trendy allure. They feature tinted lenses with rhinestone trim for a hint of glam, rubber nose supports, and a comfortable fit. Complete the look in a basic midi dress for shopping and grabbing coffee!

Fit & Features
- Tinted lenses with rhinestone trim
- Rubber nose supports
- Comfortable fit
- 100% UV protection
Style Number/Barcode: 07008-1079

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Playful Distraction Low Rise Ruffled Mini Skirt
Be a playful distraction in this low-rise mini skirt this summer! Crafted from jacquard pattern woven fabric, it's the perfect way to make a stylish statement with a touch of whimsy. Features a low-rise waist paired with a tiered ruffled silhouette creating a flirty mini-length hem. Complete the look in a crop top and platform sneakers!

Fit & Features
- Jacquard pattern, woven fabric lined with stretchy knit
- Low rise waist
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06401-0674

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine Babe Ditsy Floral Cropped Tube Top
Radiate sunny vibes in the cutest cropped tube top! Designed with an adorable ditsy floral print on stretchy smocked knit fabric, it features a strapless straight-across neckline, a cropped hem, a dainty ruffled trim, and a form-hugging fit. Style with denim shorts and sneakers.

Fit & Features
- Ditsy floral print
- Stretchy smocked ribbed knit fabric
- Strapless straight neckline
- Cropped hem
- Ruffled trims
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-1901

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Living In The Palms Wide Leg Palazzo Pants
Escape to a tropical island in these breezy palm print palazzo pants perfect for dinners with a view or exploring with a cocktail in hand! These pants have a flattering high-rise elastic waistband and wide-leg silhouette for style and comfort on stretchy knit palm print fabric. Complete the look with the matching top.

Shop Matching Top: Living In The Palms Tie-Front Crop Top

Fit & Features
- Palm print, stretchy knit fabric
- High-rise elastic waistband
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2462

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Coastal Glam Starfish Stud Earrings
Serving coastal glam in the cutest way—these starfish stud earrings are like a little vacation for your ears. Lightweight and luxe, they’re the perfect finishing touch for everything from sundresses to oversized button-downs.

Fit & Features
- Gold-dipped stainless steel
- Large starfish design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000162

Category Name: Vacation Looks

Price: $9.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Crushin' On You Lace Trim Babydoll Floral Crop Top
Look and feel like a precious flirt in this babydoll crop top! Made from an airy mesh fabric with an adorable floral print, this top features a delicate lace trim V-neckline, spaghetti straps, and a layered ruffled crop hem. Complete the look in denim shorts and sandals for casual plans!

Fit & Features
- Floral print, mesh fabric, bust lining
- Spagehtti straps
- Lace trim V-neckline
- Layered ruffled crop hem
- Runs true to size
Style Number/Barcode: 06001-5413

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On The Prowl High Rise Zebra Maxi Skirt
On the prowl and ready to unleash fierceness in this zebra print maxi skirt! It features a flattering high-rise waist with an elastic banded back for added stretch, a high front slit to show some leg, and a flowy maxi silhouette. Complete the look with the matching top.

Shop Matching Top: On The Prowl Strapless Zebra Crop Top

Fit & Features
- Zebra print, woven fabric
- High-rise waist with elastic banded back
- High front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 06301-0191

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Looks V-Neck Lace Babydoll Dress
Sweeten any occasion in this lace babydoll dress with a charming ruffled silhouette and mini-length hem!

Fit & Features
- Lace fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Ruffled babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000643

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M
Sweet Sun Floral Tie-Front Bikini Top
Enjoy the sweet sunshine at the pool or beach in this floral tie-front bikini top! Pair with the matching bikini bottoms.

Fit & Features
- Floral print, knit lined fabric
- Short puff sleeves
- Tie-front design
- Ruffled trim
- Runs true to size
Shop The Matching Bikini Bottoms: Sweet Sun Floral Bikini Bottoms
Style Number/Barcode: 07104-0726

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Laid Back Cutie High-Rise Wide-Leg Pants
Unleash your inner laid back cutie with these high-rise wide-leg pants. The drawstring waist and side pockets provide comfort and convenience, while the flowy gauze woven fabric adds a touch of bohemian charm. Complete the look in a basic crop top for casual plans or travel!

Fit & Features
- Gauze woven fabric, no stretch
- High rise drawstring waist
- Side pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0813

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Oh So Sweet Tie Back A-Line Mini Dress
You're going to look so sweet in this A-line mini dress for weekend plans! Featuring cap sleeves, a square neckline, and a tie-back design to turn heads. The A-line silhouette and mini-length hem will have you looking effortlessly chic! Complete the look in platform shoes.

Fit & Features
- Smooth knit fabric lined with stretchy knit
- Square neckline
- Tie back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5682

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Alluring 'Fit Plunging Halter Mini Dress
Create an alluring 'fit for sunset drinks in this textured knit mini dress featuring a plunging V-neck with a bust tie accent, halter straps, and a bold open back with a tie-back design. The short, bodycon silhouette will flaunt your gorgeous curves.

Fit & Features
- Sheer textured knit fabric with knit lining, high stretch
- Sleeveless plunging V-neckline, bust tie accent
- Tie-back halter spaghetti straps
- Open back, tie-back spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000020

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Best In Style Halter Button Up Vest
You'll be voted best in style wearing this sleeveless vest perfect for weekend getaways or brunch with the ladies! The vest boasts a chic halter neckline, a partially open back to reveal some skin, button front closures, and a cropped hem to flaunt your cute self. Complete the look in trouser pants and mules for an effortless flair.

Fit & Features
- Twill cotton woven fabric, no stretch
- Halter strap with button closures
- Button front closures
- Faux pockets
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1715

Category Name: Vacation Looks

Price: $15.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Dream Crochet Espadrille Platform Sandals
These boho crochet espadrille platform sandals are a summer dream! They feature an open square-shaped toe, double-banded straps with a cute multi-colored crochet design, an open back for effortless on-and-off styling, and a tall espadrille platform sole and wide block heel. Style with a flowy sundress.

Fit & Features
- 4" Wide block heel
- Espadrille material, faux leather upper
- Open square toe
- Double-banded straps, multi-colored crochet design
- Open back, on-and-off styling
- Platform sole
- Luxe fit cushion insole
- Runs true to size
Style Number/Barcode: 07401-4721

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cabana Honey Tie Front Crochet Crop Sweater
Head to the cabana in this stylish crochet crop sweater perfect for layering over your swimsuit! Featuring long sleeves with flare cuffs for added trendiness, dual tie-front closures, and a cropped hem that flaunts your figure. Complete the look with sunnies.

Fit & Features
- Sheer crochet fabric, no stretch
- Dual tie-front closures
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1743

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dose Of Sweetness Bodycon Floral Mini Dress
Ditsy florals add sweetness to this bodycon mini dress you'll adore for casual summer plans! Designed with a sheer eyelet knit fabric with a knit lining, this dress offers plenty of stretch for comfortable wear. It features adjustable spaghetti straps, a sleeveless square neckline with a dainty lace trim, ruching at the bust accented with a mini flower detail, and a flattering bodycon fit with a mini-length hem. Complete the look with earrings and sneakers.

Fit & Features
- Ditsy floral print
- Sheer eyelet knit fabric with knit lining, plenty of stretch
- Adjustable spaghetti straps
- Square neckline, dainty lace trim
- Ruched bust with mini flower detail
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5730

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
By the Shore Starfish Bracelet
Bring a little beachy charm to your stack with this starfish wire bracelet. Dainty yet eye-catching, it’s the perfect piece for layering or rocking solo.

Fit & Features
- Starfish charm insets
- Slim design
- Push-clasp closure
Style Number/Barcode: 07003-000142

Category Name: Vacation Looks

Price: $8.90

Availability: Out of Stock
Product Badge:
- Ships Free
Marvelous Darling Lace-Up Floral Chiffon Dress
This floral chiffon dress is a must-have for any fashionista attending many events this season! With a floral print and ruffled hem, this fit-and-flare dress is both charming and chic. The V-neckline and ruffled straps add a touch of flirty femininity, while the open lace-up back will have everyone love swept, and is finished with a ruffled short-length hem. Complete the look with a ring set and mules!

Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- Ruffled straps
- Lace-up, back zipper and hook-eye closure
- Fit and flare silhouette
- Ruffled short-length hem
- Sticky bra or pasties recommended
- Runs true to size
Style Number/Barcode: 05101-2962

Category Name: Vacation Looks

Price: $6.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ready To Charm Halter Cutout Wide-Leg Jumpsuit
This sleeveless jumpsuit is ready to charm everyone this season! This jumpsuit features a halter neckline with a tie and strappy cutout back. The wide-leg silhouette adds a touch of breezy style to your look perfect for any occasion! Complete the look in heeled sandals.

Fit & Features
- Sheer woven fabric with woven lining, no stretch
- Halter neckline with tie
- Strappy cutout back
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1415

Category Name: Vacation Looks

Price: $11.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summertime Chic Strappy Espadrille Wedges
Level up your summertime 'fits with these chic strappy espadrille wedges. They feature an on-trend woven espadrille wedge heel, an open square-shaped toe, an asymmetric strappy design across the foot, and thin adjustable ankle and heel straps for a customized fit with a buckle closure. Style with a floral dress for weekend brunch!

Fit & Features
- 4" Espadrille wedge heel
- Faux leather upper
- Open square toe
- Asymmetric strappy design
- Adjustable ankle and heel straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-0338

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wrap Around The Block Strappy Platform Sandals
Take a stylish walk around the block in these platform sandals featuring a round toe, asymmetrical faux leather strap, and an adjustable ankle strap with buckle closure. Complete the look in a breezy maxi dress for vacation or weekend plans!

Fit & Features
- Round toe
- Asymmetrical faux leather straps
- Platform sole
- Adjustable ankle strap with buckle closure
- Runs true to size
Style Number/Barcode: 07404-1234

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend Mood Crochet Cropped Sweater
This cropped sweater is designed with a breezy open crochet knit fabric, creating a bold sheer look perf for weekend getaways. It features a wide boat neckline and long bell sleeves to give off those effortlessly chic vibes. Style with the matching maxi skirt.

Shop Matching Bottoms: Weekend Mood Crochet Maxi Skirt

Fit & Features
- Open crochet knit fabric, minimal stretch
- Boat neckline
- Long bell sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2113

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Getaway Attitude Off-The-Shoulder Crochet Top
Serve a cute attitude for your next getaway in this off-the-shoulder crochet top. Crafted from sheer crochet knit fabric that brings dreamy vibes, this top features long bell sleeves, a bungee halter strap with beading that creates the front adjustable ruching so you customize the style, and a cropped hem. Complete the look in printed flare pants for a vacay or festival!

Fit & Features
- Sheer crochet knit, bust lining
- Off-the-shoulder
- Bungee halter strap with beading
- Adjustable ruching
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5097

Category Name: Vacation Looks

Price: $6.97 $29.90

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