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.

Twist Of Fate Snake Print Crop Top
It must be of a twist of fate how this crop top landed in your closet! It features long sleeves, crew neck, front keyhole, twisted cropped hem, snake pattern. Complete the look in a chic skirt.

Fit & Features
- Long sleeves
- Front keyhole, twisted crop hem
- Snake pattern
- Brushed knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 06001-3890

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual And Trendy Tie-Front Top
Casual and trendy, this basic crop top is a stylish must-have. It features a notched front V-neckline, short sleeves, a cute tie-front design, and a cropped, form-hugging fit. The soft brushed knit fabric offers plenty of stretch. Style this top with high-rise jeans.

Fit & Features
- Notched front V-neckline
- Short sleeves
- Tie-front detail
- Cropped, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06202-0277

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Flirtatious Floral Midi Dress
Bring the flirtatious vibes in this gorgeous floral printed midi dress. It features a sleeveless V-neckline with a wrap-front design, spaghetti straps, a high waist seam, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with sleek hoop earrings and chic block heels.

Fit & Features
- Sleeveless V-neckline, wrap-front design
- Spaghetti straps
- High waist seam
- Mid-length, form-fitting silhouette, asymmetrical hem
- Side ruched detailing
- Floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1488

Category Name: Vacation Looks

Price: $5.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Bae Flare Pants
You'll be such a boho bae in these flare pants perf for music festival season! They feature a high-rise elastic waist, paisley mixed pattern, and a flared hem on soft brushed knit fabric with a moderate stretch. Style with the matching top.

Shop The Matching Top: Boho Bae Tie-Front Crop Top

Fit & Features
- High-rise elasticized waist
- Flared hem
- Paisley mixed pattern
- Soft brushed knit fabric
- Pull-on/off styling
- Fits true to size, moderate stretch
Style Number/Barcode: 06502-0778

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Girl Flare Pants
Every boho girl's fav essential is her flare pants! These high-rise pants feature an elasticized waist, a paisley mixed pattern, and a flared hem on soft brushed knit fabric with a moderate stretch. Complete the look in a basic crop top.

Fit & Features
- High-rise elasticized waist
- Paisley mixed pattern
- Flared hem
- Soft brushed knit fabric
- Pull-on/off styling
- Fits true to size, moderate stretch
Style Number/Barcode: 06502-0781

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Out Of Town Lace-Up Chiffon Romper
Jetset out of town looking so fab in this chiffon romper perfect for dinner and dancing! It features long peasant sleeves, a plunge V-neckline, an open-back with a sultry lace-up design, and tiered shorts. Complete the look in glitzy heels.

Fit & Features
- Long peasant sleeves, elastic cinched hems
- Plunge V-neckline
- Open-back, lace-up closure
- Tiered shorts
- Chiffon lined fabric
- Runs true to size
Style Number/Barcode: 06403-0218

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sleek And Sultry Tie Front Crop Top
Sleek and sultry, this tie front crop top makes the perfect instant outfit with the matching skirt!

Fit & Features
- Smooth knit fabric, moderate stretch
- V-neckline
- Tie front
- Cropped hem
- Runs true to size
Shop The Matching Skirt: Sleek And Sultry Bodycon Ruffle Mini Skirt
Style Number/Barcode: 06202-000031

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Key Essential Halter Crop Top
Stunning and effortless, this halter crop top is a key essential to elevate your night out look! It features a sleeveless, mock neck with dual button closures, a sultry front, and a back slit. Composed of a brushed knit fabric with a moderate stretch. Style with high-rise jeans and strappy mules.

Fit & Features
- Mock neck, dual button closures
- Front and back slit accent
- Cropped hem
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4202

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Amalfi Coast Plunge Neck Mermaid Floral Maxi Dress
Enjoy a sunset dinner and drinks in this floral maxi dress along the Amalfi Coast! With sultry details and a mermaid silhouette that flaunts your curves, this dress will turn heads.

Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Plunge halter cowl neckline, tie closure
- Mermaid silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000052

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty Ties V-Neck Wrap Top
The prettiest wrap crop top you've ever seen! It features short sleeves, a V-neckline, and a wrap tie-waist on sleek knit fabric with a moderate stretch. Complete the look with jeans and sandals for a stylish fit.

Fit & Features
- Short sleeves
- V-neckline
- Wrap tie-waist
- Cropped hem
- Sleek knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4080

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Classic Faux Wool Panama Hat
Keep it classic with a panama hat that completes your look! The hat features a classic panama design, a belted trim with a bow accent, and a wide brim. Complete look with a floral top and belted pants.

Fit & Features
- Panama design
- Belted trim
- Bow accent
- Wide brim
- Faux wool material
Style Number/Barcode: 07302-0513

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Classic And Sleek Cat-Eye Sunglasses
Classic and oh-so-sleek, these sunglasses are perfect for achieving that chic vibe. They feature a square-shaped cat-eye design with a tortoise-shell printed plastic frame and tinted lenses. Complete the look with a crossbody purse.

Fit & Features
- Square cat-eye design
- Tortoise-shell printed plastic frame
- Small gold stud detailing
- Tinted lenses
- 100% UV Protection
Style Number/Barcode: 07008-0917

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Get That Glow Rhinestone Belt
Glow and shine everywhere in this statement rhinestone belt featuring a 5-row design and an adjustable buckle closure. Complete the look in a sleek satin dress for the perfect finishing touch.

Fit & Features
- Rhinestone 5-row design
- Adjustable buckle closure
- Metal material
Style Number/Barcode: 07301-0422

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Trendy Moves Midi Dress
Make the trendiest of moves in this cool printed midi dress. It features a sleeveless halter neckline with spaghetti straps that lead to an open back with a strappy lattice design, a fitted bodice leading to a subtle flowy silhouette with a thigh-high front slit, and an all-over splattered tie-dye print. Style this dress with clear mules.

Fit & Features
- Sleeveless halter neckline, spaghetti straps
- Open back, strappy lattice design, tie closure
- Fitted bodice, flowy silhouette, high front slit
- Spattered tie-dye print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4371

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Golden Girl Satin Tie-Front Top
You'll be the golden girl when it comes to style! Create a sultry look in this tie-front top featuring long peasant sleeves, a plunge v-neckline, floral pattern, and a cropped hem. Complete the look in a cute mini skirt.

Fit & Features
- Long peasant sleeves
- Plunge v-neckline
- Tie-front crop hem
- Floral pattern
- Satin fabric
- Fits true to size, no stretch
Style Number/Barcode: 06204-1250

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Damsel In Distress High-Rise Mom Shorts
You may be a damsel in distress, but at least you're well dressed in these high-rise mom shorts! They feature edgy distressed accents on the front and a frayed hem on light wash denim fabric with no stretch. Complete the look in a graphic top and sneakers.

Fit & Features
- High-rise waist
- Distressed accents on the front
- Mom style, frayed hem
- Front button and hidden zipper closure
- Classic 5-pocket design, belt loops
- Light wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0267

Category Name: Vacation Looks

Price: $13.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
LA Scene Distressed Mom Shorts
Steal the scene in the big city! These high-rise mom shorts feature distressed accents, a frayed hem, and side slit accents. The medium-wash cotton fabric offers no stretch. Complete the look in a trendy crop top.

Fit & Features
- High-rise waist
- Mom style
- Side slit accents, frayed hem
- Button and hidden zipper closure
- Classic 5-pocket styling, belt loops
- Medium wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0269

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spring Floral Long Sleeve Duster
Florals for spring! Level up your outfit in this long sleeve duster featuring an open-front, longline hem on sheer, mesh knit fabric with a moderate stretch. Complete the look in a lacey bralette and jeans.

Fit & Features
- Long sleeves
- Open-front
- Longline hem
- Floral pattern
- Sheer mesh knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 06202-0278

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simple Sparkle Rhinestone Belly Chain
Showcase some simple sparkle with this chic belly chain. It features a dainty chain-link design with small rhinestone embellishments and an adjustable fit. Style this chain over a fitted bodycon dress or with cinched high waist dress pants.

Fit & Features
- Chain-link design
- Single row of small rhinestone embellishments
- Adjustable chain, lobster clasp closure
Style Number/Barcode: 07301-0453

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fashion Jelly Quilted Crossbody
Get on the jelly trend with this crossbody bag featuring a diamond quilt pattern, turn-lock closure, chain-link strap, and a spacious interior. Complete the look in cute slides.

Fit & Features
- Diamond quilt pattern
- Turn-lock closure
- Chain-link strap
- Spacious interior
- Jelly material
Style Number/Barcode: 07203-0923

Category Name: Vacation Looks

Price: $8.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Frolic Mesh Duster
Frolic in florals. Elevate your outfit in this long sleeve duster featuring an open-front design, longline hem, and a flowy fit. Composed of sheer mesh knit fabric with a moderate stretch. Finish the look in a beaded bustier and jeans.

Fit & Features
- Long sleeves
- Open-front design
- Longline hem
- Flowy fit
- Floral pattern
- Sheer mesh knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 06202-0265

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tulum String Bikini Bottoms
The perfect bikini for your next vacay in Tulum! It features a mid-rise waist, side string straps, and a cheeky fit. Complete the look in the matching bikini top.

Shop The Matching Bikini Top: Tulum Triangle Bikini Top

Fit & Features
- Mid-rise waist
- Side string straps
- Cheeky fit
- Fits true to size
Style Number/Barcode: 07105-0808

Category Name: Vacation Looks

Price: $4.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffle Repeat Lace Tube Mini Dress
She’s sleek up top, party on the bottom—aka your new go-to for nights that need a little extra twirl. The strapless neckline and tiered ruffles make it an easy yes for going out.

Fit & Features
- Lace fabric, stretchy knit lining
- Strapless tube neckline
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000171

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tulum Triangle Bikini Top
The perfect bikini for your next vacay in Tulum! It features a classic triangle cup design, plunge neck, a back hook closure, and adjustable straps so you can customize the fit. Complete the look in the matching bikini bottoms.

Shop The Matching Bikini Bottoms: Tulum String Bikini Bottoms

Fit & Features
- Triangle cup design
- Removable padding
- Plunge neck
- Back hook closure
- Adjustable straps
- Fits true to size
Style Number/Barcode: 07104-0661

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials