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

Discover Short Sleeve Dresses

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Get Eye-Catching Sandals For Women

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.

Summer Spice Lace-Up Ruffle Crop Top
Set the tone in this spicy ruffled crop top with a lace-up back that turns heads! Pair with the matching shorts to complete the vibe.

Fit & Features
- Mesh-lined fabric
- Cap sleeves
- Crew neck
- Ruffled crop hem
- Bungee strap lace-up back
- Runs true to size
Shop The Matching Shorts: Summer Spice Low-Rise Ruffle Hot Shorts
Style Number/Barcode: 06001-000034

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: BLACK, PINK

Available Size: S, M, L
Product Badge:
- Sale
Strut It Lace-Up Stiletto Heels
Strut all around town in these super sultry pair of stiletto heels! They feature lace-up ankle ties, an open toe, and a stiletto heel. Wear them with a bodycon dress for your next GNO!

Fit & Features
- Lace-up tied ankle
- Open toe
- Stiletto heel
- Fits true to size
Style Number/Barcode: 07401-3121

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Trendy Braided Block Heel Mules
Stay on trend with mules that keep your look on point! The mules feature an open back, a double braided strap design, an open square toe, and a block heel. The mules are composed of a faux leather material. Complete look with a midi dress and hoops.

Fit & Features
- Open back
- Double braided strap design
- Open square toe
- Block heel
- Faux leather material
- Runs small
Please be advised that these heels run a 1/2 size too small.
Style Number/Barcode: 07401-3545

Category Name: Vacation Looks

Price: $16.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Beauty A-Line Midi Dress
Bring a sweet style to your everyday look with this adorable flowy midi dress. It features a square neckline, half-length puff sleeves, a partially smocked back, a high waist, and a mid-length, A-line silhouette with a tiered hem. Complete the outfit with sleek hoop earrings and cute mules.

Fit & Features
- Square neckline
- Half-length puff sleeves, elastic cinched hems
- Partially smocked back
- High waist
- Mid-length, A-line flowy silhouette, tiered hem
- Cotton fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4243

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ella High Rise Distressed Mom Jeans
Keep it lowkey in jeans that are perf to pair with your dressy and casual tops! The dark-wash jeans feature a high-rise waist, a light distressing, and a straight-leg fit. Complete the look with a cable knit sweater and ankle booties.

Fit & Features
- High rise waist
- Front-button, hidden zipper closure
- Five-pocket with belt loop design
- Light distressing
- Straight leg fit
- Dark-wash denim fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06602-0248

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Minimal And Chic Ribbed Knit Pajama Jumpsuit
This minimal and chic pajama jumpsuit is perf for looking stylish as you lounge at home! It features a sleeveless V-neckline, spaghetti straps, and a form-hugging silhouette with fitted pant legs. The lightweight ribbed knit fabric offers plenty of stretch for comfortable wear. Complete the look with cute slides.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Form-hugging silhouette
- Fitted pant legs
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 07103-0649

Category Name: Vacation Looks

Price: $8.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fierce And Fabulous Mini Dress
Fierce and fab will be your go-to vibe in this sexy mini dress. It features a square neckline, spaghetti straps, a lower back cutout, ruched detailing, and a short, curve-hugging fit. The stretchy knit fabric has an on-trend all-over leopard print. Complete the look with clear heels.

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Lower back cutout
- Ruching
- Mini-length, form-fitting silhouette
- Lined knit fabric, moderate stretch, leopard print
- Runs true to size
Style Number/Barcode: 05103-3910

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Deets Panama Hat
This cute Panama hat has chic details to get a trendy look this fall season. It features a flat brim with a thin chain-link trim around the center to add an edgy glam vibe. Style this hat with ankle booties.

Fit & Features
- Flat brim
- Chain-link trim
- Faux wool material
Style Number/Barcode: 07302-0372

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casually Fab Tie-Dye Mini Dress
Get a casually fab look in this on-trend tie-dye mini dress. It features a crew neckline, short sleeves, ruched detailing down the sides with ties at the hem, and a short, curve-hugging silhouette. Style this dress with a denim jacket and sneakers.

Fit & Features
- Crew neckline
- Short sleeves
- Ruching down the sides
- Ties at the hem
- Mini-length, form-hugging fit
- Ribbed knit fabric, plenty of stretch, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4233

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Gotta Be Chic High Rise Destructed Mom Jeans
Stay on trend with jeans that bring out those vintage vibes! The jeans feature a high-rise waist, mom-styled leg, heavy destruction, and a relaxed fit. The dark denim jeans offer a minimal stretch. Complete look with a bodysuit and chunky sneakers.

Fit & Features
- High rise waist
- Heavy destruction
- Mom-styled leg
- Dark denim fabric
- Relaxed fit, minimal stretch, runs true to size
- Single-button with zipper closure
- Traditional five-pocket with belt loop design
Style Number/Barcode: 06602-0294

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Taking The Plunge Ruched Halter Dress
Take the plunge with a dress that reveals more than a hint of skin! The dress features a twist halter neck with a keyhole at the bust, a ruched drawstring, a high side slit, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels.

Fit & Features
- Twist halter neck
- Keyhole at bust
- Ruched drawstring, high side slit
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4073

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bound To Stun One Shoulder Mini Dress
You were born to stun babe, impress with a mini dress that draws all eyes on you! The dress features a one-shoulder neckline, tank shoulder strap, side waist cutout, and a ruched mini-length silhouette. Complete look with mules.

Fit & Features
- One-shoulder neckline
- Tank shoulder straps
- Side waist cutout
- Ruching
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05103-4027

Category Name: Vacation Looks

Price: $5.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stunning Style Snake Print Mini Dress
Showcase a stunning, sassy style in this trendy snake print mini dress. It features a sleeveless scoop neckline with shirring at the bust, adjustable spaghetti straps, ruching down the sides, and a short, form-hugging fit. Complete the look with sleek hoop earrings.

Fit & Features
- Sleeveless scoop neckline
- Shirring at the bust
- Adjustable spaghetti straps
- Ruching down the sides
- Mini-length, form-fitting silhouette
- Lined knit fabric, moderate stretch, snake print
- Runs true to size
Style Number/Barcode: 05103-3927

Category Name: Vacation Looks

Price: $6.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stack It Up PVC Crisscross Block Mules
Stack up your height in this pair of covetable mules! They're designed with a block heel, a clear crisscross PVC strap, and an open toe. Wear them with a tie-front top and jeans for a Insta-worthy look.

Fit & Features
- Crisscross clear PVC strap
- Block heel
- Open toe
- Fits true to size
Style Number/Barcode: 07401-3544

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Golden Hour Tube Top Energy
She’s luxe, bold, and lowkey lethal. With gleaming metal hardware and a tropical print that’s giving goddess getaway, this tube top brings the heat wherever you wear her—beach club or rooftop takeover. Pair with the matching bottoms.

Shop Matching Bottoms: Golden Hour Wide Leg Pants Energy

Fit & Features
- Tropical print, stretchy knit fabric
- U-cut out strapless tube neckline, hardware insert
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06001-000153

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Don't Call It Basic Strap Sandal
You know you'll be comfortable and on-trend all day in this must-have pair of sandals! It's designed with a thick strap, buckled ankle strap, and open toe. Wear it with a floral top and jeans for casual-chic style.

Fit & Features
- Open toe
- Thick strap
- Buckled ankle strap
- Fits true to size
Style Number/Barcode: 07404-0890

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Picnic Please Braided Block Heels
Soak up the sun in this pair of block heels! They're designed with braided straps and an open almond toe. Finish your look off with a sweet sundress.

Fit & Features
- Open almond toe
- Braided straps
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3317

Category Name: Vacation Looks

Price: $12.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep Blooming Rhinestone Flower Earrings
Stay blooming babe in this gorgeous pair of flower earrings! They feature a matte design with different-sized flowers and rhinestone accents. Wear them with a sundress for an in full bloom look.

Fit & Features
- Different sizes of flowers
- Matte design
- Rhinestone accents
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0892

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
No Hands Croc Embossed Fanny Pack Belt
Go totally hands-free babe with this fanny pack belt! It's designed with cross-embossed faux leather material, envelope-style front, and snap button closure. Wear with a romper for the ultimate music festival vibes.

Fit & Features
- Removable faux leather belt
- Envelope style front
- Snap-button closure
Style Number/Barcode: 07203-0807

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Good Vibes Only Croc Embossed Fanny Pack Belt
Bring the good vibes on with this mini fanny pack belt! It's made from faux leather with a croc-embossed design, a removable belt strap, and chain detail. Rock on with faux leather leggings.

Fit & Features
- Adjustable faux leather belt
- Mini fanny pack
- Snap-button closure
- Removable chain accent
Style Number/Barcode: 07203-0811

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
The Everday Espadrille Platform Wedges
Keep it casually chic with platform wedges that keep it lowkey! The platform wedges feature an open back, an adjustable ankle strap, a triple-row strap design, and an espadrille platform. Complete look with a cute matching top and skirt set.

Fit & Features
- Open back
- Adjustable ankle strap
- Triple-row strap design
- Espadrille platform
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0947

Category Name: Vacation Looks

Price: $7.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sultry Strappy Waist Sleeveless Midi Dress
This ribbed knit midi dress is the perf option for a casual yet still sultry look! It features a sleeveless crew neckline, tank shoulder straps, a front waist cutout with a strappy design, and a mid-length, curve-hugging silhouette with a chic side slit. Style this dress with strappy heels.

Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Front waist cutout, strappy design
- Mid-length, form-hugging fit
- Side slit
- Lined ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4272

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cozy And Chill Pajama Shorts
Chill out in cute pajama shorts that will keep you stylish and comfy! The shorts feature an elastic high rise waist, drawstring waist, hidden side pockets, and a mid-thigh length. The shorts are composed of a soft-to-the-touch knit fabric that offers a relaxed fit with a moderate stretch. Complete look with the matching pajama tank.

Shop Matching Pajama Tank: Cozy And Chill Pajama Tank

Fit & Features
- Elastic high rise waist
- Drawstring waist
- Mid-thigh length
- Hidden side pockets
- Knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0653

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Retro Mood Tie Dye Midi Dress
Channel a retro mood with a midi dress that is totally fab! The dress features a tie-dye print, a crew neckline, short sleeves, and a high side slit with a twist knot accent. The dress is composed of smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a denim jacket.

Fit & Features
- Crew neckline
- Short sleeves
- High side slit, twist knot accent
- Tie-dye pattern
- Midi length silhouette
- Cotton kbit fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4271

Category Name: Vacation Looks

Price: $9.97 $29.90

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