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.

Picnic Date Ditsy Floral Chiffon Romper
This adorable ditsy floral chiffon romper will have you picture-perfect for a picnic date! It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist with a sheer floral crochet trim, flowy shorts, and a fit and flare silhouette. The airy chiffon fabric features a dainty ditsy floral print pattern. Complete the look with espadrille sandals.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, back zipper closure
- High waist, sheer floral crochet trim
- Flowy shorts, fit and flare silhouette
- Ditsy floral print
- Sheer chiffon fabric, lining
- Runs true to size
Style Number/Barcode: 06403-0252

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Denim Daze Button Crop Vest
The perfect denim vest to give our outfit a cute western vibe! It features a sleeveless V-neck, button-down front, faux pockets, and a curved crop hem. Style with best-selling bottoms for a festival or an art walk downtown!

Fit & Features
- Sleeveless V-neck
- Button-down front
- Faux pockets
- Curved, crop hem
- Non-stretch rifid denim fabric
- Runs true to size
Style Number/Barcode: 06203-0491

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feel The Rhythm Crochet Lace-Up Vest
Feel the rhythm in this crochet vest perfect for festivals or concerts! It features a sleeveless V-neckline, wide shoulder straps, a front lace-up design, and a pointed crop hem. Complete the look in trendy denim shorts.

Fit & Features
- Sleeveless V-neckline
- Wide shoulder straps
- Front lace-up design
- Pointed crop hem
- Crochet fabric, sewn-in knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4803

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Meet In The Hamptons Linen Crop Top
This linen crop top has a Hampton's getaway written all over it! Look cute strolling through the town in this top featuring a sleeveless halter V-neckline and dual tie-back neck and lower back straps. Style with the matching bottoms and a dainty necklace to complete the chic look!

Shop Matching Bottoms: Meet In The Hamptons Linen Wide Leg Pants

Fit & Features
- Sleeveless halter V-neckline
- Dual tie-back neck and lower back straps
- Cropped hem
- Lined linen fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2163

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All The Attention Abstract Split Crop Top
Command attention in this striking halter crop top featuring a flattering twisted neckline, a daring split design, and a cropped length that perfectly highlights your figure.

Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining
- Halter plunge twist neckline, tie closure
- Center split design
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000167

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Artsy Blooms Floral Mini Skirt
Create an artsy-chic look with this floral mini skirt for an evening downtown! It features a high-rise waist, a front ruched seam atop a slit hem, and a bodycon silhouette on stretchy mesh-lined fabric. Style with a crop top and heels.

Fit & Features
- High-rise waist
- Front ruched seam
- Bodycon silhouette
- Mini-length hem with slit
- Floral artsy bloom print
- Mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0802

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Look Your Cutest Floral Chiffon Mini Skirt
Look your cutest in this floral mini skirt for a stylish stroll downtown to brunch! It features a high-rise waist, a form-hugging fit, and an asymmetrical ruffle trim on airy chiffon fabric. Complete the look in a basic strapless top and heels.

Fit & Features
- High-rise waist
- Hidden side zipper and hook-eye closure
- Form-hugging fit
- Asymmetrical ruffle trim, mini-length hem
- Ditsy floral print
- Airy chiffon woven fabric
- Runs true to size
Style Number/Barcode: 06401-0490

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Miami Nights Ruched Mini Skirt
Bring the heat and take on the night scene in this alluring mini skirt! It features a high-rise elasticized waist, ruched detailing down the side and back seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric offers plenty of stretch. Style with the matching crop top and a pair of strappy stilettos.

Shop Matching Top: Miami Nights One-Shoulder Crop Top

Fit & Features
- High-rise elasticized waist
- Ruched side and back seams
- Mini-length hem
- Form-hugging fit
- Sheer mesh fabric, full knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0783

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Miami Nights One-Shoulder Crop Top
Bring the heat and take on the night scene in this alluring crop top! It features a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap, ruched detailing, and a fitted cropped hem. The lined mesh fabric offers plenty of stretch. Style with the matching mini skirt and a pair of strappy stilettos.

Shop Matching Bottoms: Miami Nights Ruched Mini Skirt

Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Single adjustable spaghetti strap
- Ruching
- Fitted cropped hem
- Sheer mesh fabric, full knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4672

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cute Find Lace-Up Cork Block Heels
Embrace the warmer months with these cork block heels that are the cutest find! They feature an open almond-shaped toe, a thin strappy design across the foot, a heel strap, a thin lace-up strappy design that wraps around the leg, and a cork block heel. Style with a mini handbag.

Fit & Features
- Open almond-shaped toe
- Thin strappy design across the foot
- Heel strap
- Thin strappy lace-up wrap-around design, tie closure
- Cork block heel
- Faux leather insole and straps
- Runs true to size
Style Number/Barcode: 07401-4315

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Glam Rhinestone And Pearl Sandals
These effortless glam embellished sandals are a perfect pick for the summer season! They feature a square-shaped toe, dual clear straps with pearl embellishments, a two-row rhinestone outline along the flat sole, and an open back for easy on-and-off styling. Pair these sandals with a mini handbag.

Fit & Features
- Square-shaped toe
- Dual clear PVC straps
- Pearl embellishments
- Two-row rhinestone outline, flat sole
- Open back
- Runs true to size
Style Number/Barcode: 07404-1108

Category Name: Vacation Looks

Price: $12.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirt On Arrival Denim Skater Dress
Made for flings, flirts, and feelin’ yourself. This trendy halter skater dress hugs you in all the right places with a playful bust cutout and a twirl-worthy drop waist—aka your weekend wardrobe’s new fave.

Fit & Features
- Denim fabric
- Sleeveless cross-front halter neckline, tie-back straps
- Bust cutout, metal heart accent
- Partially open back, hidden lower back zipper closure
- Drop waist
- Short pleated skater silhouette
- Runs small, size up recommended
Style Number/Barcode: 05102-000084

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ready For It Faux Leather Lace-Up Wedges
You'll be ready for a fabulous night out in these bold lace-up wedges! They feature an open almond-shaped toe with a strap, thin criss-cross straps across the foot, a heel strap, thin lace-up straps that wrap around the leg, and a tall, sturdy wedge heel. Style with a chic crossbody bag.

Fit & Features
- Open almond-shaped toe, strap
- Thin criss-cross straps across the foot
- Heel strap, thin lace-up straps
- Wrap-around design, tie closure
- Tall wedge heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-0334

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cute Factor Eyelet Lace Skater Dress
Bring the cute factor by wearing this eyelet lace skater dress for picnics, brunch, or casual family parties! Featuring adorable puff short sleeves, a square neck with a ruched bust, a flirty tie-back closure, and a fit-and-flare silhouette and short hem. Complete the look with cute flower earrings.

Fit & Features
- Puff short sleeves
- Square neck, ruched bust
- Tie-back closure
- Skater, fit and flare silhouette
- Short-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4910

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
My Favorite Chiffon Floral Crop Top
This chiffon crop top will be your favorite for day dates or coffee with friends! It features dreamy sheer peasant sleeves, a sweetheart neckline, a twisted bust, a stretchy smocked back, and an ultra-cropped hem. Style with high-rise jeans and sandals to complete the look!

Fit & Features
- Sheer peasant long sleeves
- Sweetheart neckline, twisted bust
- Ultra cropped hem
- Stretchy smocked back
- Blooming floral print
- Lined airy chiffon
- Runs true to size
Style Number/Barcode: 06003-2151

Category Name: Vacation Looks

Price: $4.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Quick Instinct Zebra Print Mesh Flare Pants
If your instincts lead to these zebra print flare pants...they belong in your cart! Featuring a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flared hem on a mesh fabric. Complete the look with the matching bustier.

Shop Matching Top: Quick Instinct Zebra Print Mesh Bustier

Fit & Features
- High-rise waist
- Hip-hugging fit
- Form-hugging fit throughout the legs
- Flared hem
- Zebra print
- Mesh fabric
- Runs true to size
Style Number/Barcode: 06502-2257

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Quick Instinct Zebra Print Mesh Bustier
If your instincts lead to this zebra print bustier...it belongs in your cart! Featuring a strapless and structured bodice with flexible boning, a pointed crop hem, and a back zipper and hook-eye closure on a lined mesh fabric. Complete the look with the matching flare pants.

Shop Matching Bottoms: Quick Instinct Zebra Print Mesh Flare Pants

Fit & Features
- Strapless and structured bodice
- Flexible boning
- Pointed crop hem
- Back zipper and hook-eye closure
- Zebra print
- Lined mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4742

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Breezy Chic Crochet Trim Kimono
Layer on this breezy and chic kimono to elevate every outfit! It features short sleeves, an open-front design, a back crochet trim, and a flowy long hem. Complete the look in flat sandals for a boho style!

Fit & Features
- Short sleeves
- Open front design
- Back crochet trim
- Flowy hem
- Lightweight woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1586

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Switch It Up Wayfarer Oversized Sunglasses
Switch up your style this season in these wayfarer sunglasses perfect for wearing on beach days or at pool parties! They feature an oversized design, pink frames with sleek metal arms, and tinted pink lenses. Complete the look in a sassy matching set.

Fit & Features
- Oversized design
- Sleek metal arms
- Pink frame
- Tinted pink lenses
- 100% UV protection
Style Number/Barcode: 07008-1007

Category Name: Vacation Looks

Price: $3.96 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bold Muse Floral Print Maxi Skirt
Serve fab vibes on vacay in this maxi skirt featuring a bold floral print pattern. Style with the matching tube top for an iconic 'fit.

Shop Matching Top: Bold Muse Floral Print Tube Top

Fit & Features
- Smooth knit fabric, high stretch
- Large floral print
- Mid-rise waist
- Hip-hugging fit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000047

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Road Trippin' Classic Aviator Sunglasses
Slip on these classic aviator sunglasses during your next road trip or beach day! They feature a sleek design, a metal frame, rubber nose supports, and tinted brown lenses to help protect your eyes from the sun. Complete the look in a trendy crop denim jacket.

Fit & Features
- Sleek design
- Metal frame
- Rubber nose supports
- Tinted brown lenses
- 100% UV protection
Style Number/Barcode: 07008-1004

Category Name: Vacation Looks

Price: $3.96 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Playful Touch Crepe Daisy Print Short Dress
Add a playful touch to your closet with this adorable crepe daisy print dress to wear for birthdays or family parties! It features puff short sleeves, a sweetheart neckline, a flirty bust tie, a stretchy smocked back, hidden side pockets for keeping your hands warm, and a tiered ruffled short-length hem. Complete the look with dainty earrings.

Fit & Features
- Puff short sleeves
- Sweetheart neckline
- Bust tie front, stretchy smocked back
- Hidden side pockets
- Tiered ruffled short-length hem
- Daisy print,
Style Number/Barcode: 05101-2338

Category Name: Vacation Looks

Price: $19.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Subtle Love Ditsy Floral Mini Dress
Effortlessly cute with subtle detail, what's not to love about this ditsy floral mini dress? It features a sleeveless V-neckline with a ruched bust seam, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a brunch.

Fit & Features
- Sleeveless V-neckline, ruched bust seam
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print
- Ribbed stretchy knit fabric, knit lining
- Runs true to size
Style Number/Barcode: 05102-5073

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Can't Resist Chiffon Floral Skater Dress
No one can resist you in this chiffon floral dress - a staple for all of the upcoming soirees! It features a sleeveless V-neckline, adjustable spaghetti straps, a tie-back closure, and a flattering skater short silhouette. Complete the look in faux leather mules.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Tie-back closure
- Skater silhouette
- Short-length hem
- Floral print, chiffon fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05101-2057

Category Name: Vacation Looks

Price: $9.97 $44.90

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