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.

Falling For You Floral Mini Skirt
They will be falling for you hard when you step out in this smocked mini skirt. Don’t forget to pick up the matching crop top to complete the look!

Shop the Matching Top: Falling For You Floral Crop Top

Fits & Features
- Ditsy Floral Print
- Smocked
- Ruffle Hem
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06301-0040

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Palm Leaf High Slit Maxi Skirt
Get set for the tropics in this skirt that will transport you to an island fantasy. The skirt features a high rise waist, a tropical palm-leaf print, and a maxi silhouette with a dramatic high slit to show off a hint of leg. Complete look with matching top and statement earrings.

Shop Matching Crop Top: Tropical Palm Leaf Tube Top

Fit & Features
- High rise waist
- Tropical floral print
- Maxi length silhouette
- High side slit
- Matching top sold separately
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06501-0225

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Glow-Up Watercolor Woven Shorts
Show off a summer glow-up in these watercolor-printed woven shorts designed with a high-rise waist and a relaxed silhouette. Style with the matching tube top for a chic vibe.

Shop Matching Top: Summer Glow-Up Watercolor Woven Tube Top

Fit & Features
- Linen-like woven fabric, watercolor print, woven lining
- High-rise waist, belt loops
- Hidden front zipper and hook-eye closure
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06303-000022

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Double Row Tie Front Ribbed Crop Top
Stand out babe in this chic crop top. Head out for a beach day in this trendsetting crop top that features a plunging V-neckline, a double-row tie front accent to create a customized fit, and a cropped hem. Complete your look with your favorite high waist jeans and stunning sunglasses.

Fit & Features
- Plunging v-neckline
- Spaghetti straps
- Double-row tie front accent
- Cropped hem
- Ribbed knit fabric
- Relaxed fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-2685

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Falling For You Floral Crop Top
They will be falling for you hard when you step out in this smocked crop top. Don’t forget to pick up the matching skirt to complete the look!

Shop the Matching Bottoms: Falling For You Floral Mini Skirt

Fits & Features
- Ditsy Floral Print
- Smocked
- Spaghetti Straps
Style Number/Barcode: 06003-0531

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Destruction High Rise Boyfriend Jeans
Start off a fire 'fit with these trendy boyfriend jeans! They feature a high rise waist, a traditional five-pocket and belt loop design, distressed detailing, and straight pant legs with an ankle cut hem. Style these jeans with a cute crop top and strappy heels.

Fit & Features
- High rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Distressed detailing
- Straight pant legs with an ankle cut hem
- Denim fabric with minimal stretch
Style Number/Barcode: 06602-0068

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Gorgeous Lace-Up Striped Maxi Dress
Look gorgeous everywhere you go in this striped maxi dress! Featuring a flattering halter crew neck and a chic lace-up back, this bodycon fit dress hugs your curves for a stunning silhouette.

Fit & Features
- Striped pattern, stretchy cotton knit fabric
- Halter crew neck
- Lace-up open back
- Bodycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000009

Category Name: Vacation Looks

Price: $8.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Walk in the Park Floral Mini Dress
Take a stroll in style wearing this sweet floral dress! Pair it with sandals and a straw bag.

Fit & Features
- Ribbed Fabric
- Off the Shoulder Puff Sleeves
- Tie Front Detail
- Mini Length
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0447

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Strapless Tube Tie Dye Midi Dress
Make a splash in a tie-dye dress that brings some serious summer vibes! Step out for that backyard bbq with the squad in this colorful midi dress. The dress features a strapless tube neckline, a tie-dye print, and a curve-hugging midi-length silhouette. Complete your summer outfit with clear heels.

Fit & Features
- Sleeveless tube neckline
- Tie-dye pattern
- Midi length silhouette
- Form hugging knit fabric
- Moderate stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0831

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
High Rise Distressed Acid Wash Denim Shorts
These cut off acid wash denim shorts are a must-have in your wardrobe! They feature a high rise waist and a majorly distressed hem with a cheeky bottom. Pair with a crop top and some heeled booties for a cute day date look!

Fit & Features
- High rise waist
- Front button closure
- Traditional five pocket and belt loop design
- Majorly distressed hem
- Cheeky bottom
- Acid wash denim fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0143

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High Rise Skinny Cropped Jeans
Your favorite skinny jeans just got a new update. This pair features a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, a little distressed detailing, a slight skinny leg fit, and a cropped raw cut hem. Jeans are composed of a denim fabric with moderate stretch.

Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

Style Number/Barcode: 06602-0044

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Trip To The Tropics Strapless Jumpsuit
Feel like you're taking a relaxing trip to the tropics in this bold strapless jumpsuit! Featuring a simple strapless top and palm leaf printed flowy pants, you'll feel like you're on a getaway vacay. Perf for a nice dinner with bae, pair with some statement earrings and clear heels.

Fit & Features
- Strapless square neckline
- High waist pants
- Tie front belt
- Flowy pant legs with palm leaf print
- Knit fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06502-0427

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Mesh Tie Waist Long Duster
Cinch your look with a duster to layer with your favorite pieces! The duster features a draped open front, long sleeves, a tie waist belt, and composed of a sheer mesh fabric. Complete your look with a lace bralette and high rise jeans.

Fit & Features
- Draped open front
- Long sleeves
- Tie-waist belt
- Sheer mesh fabric
- Relaxed fit
- Moderate stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06202-0094

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flawless Finish Clear Quilted Crossbody Purse
Get the ultimate flawless finish when you add in a clear quilted purse to your look! Pair with a blazer and leather leggings, or dress down with sweats and trench coat!
- Rectangular structure
- Quilted design
- Convertible crossbody chain
- Turn lock closure
- Inner divider
- Cloudy jelly
- Gold Hardware
Style Number/Barcode: 07203-0379

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Kara Super High Rise Destructed Shorts
Oasis by Eunina

The Kara Super High Rise Destructed Shorts will be your fave of the season for sure! This black denim pair features trendy distressing and a flattering cuffed hem. Wear to go hang with the squad, paired with a chic cropped blouse and sleek heeled ankle booties.

Fit & Features
- High rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Destructed detailing
- Rolled cuffed hem
- Denim fabric with moderate stretch
Style Number/Barcode: 06603-0046

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casually Cute Slip On Sneakers
Keep it casual in sneakers to nail down those low-key outfits this season. The sneakers feature an easy slip-on design, a round toe, and a canvas material body. Complete your effortlessly casual look with a graphic tee and high waist jeans.

Fit & Features
- Slip-on design
- Round toe
- Canvas material body
- Thick sole
- Available in beige, black and camo print
Please be advised that these shoes run 1/2 a size small.
Style Number/Barcode: 07407-0064

Category Name: Vacation Looks

Price: $12.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Three Pack Cross Chain Anklet
Add a dainty detail with an anklet that brings a hint of dazzle to your favorite fits'. The pack includes three dainty chain anklets featuring a snake chain and mini cross charms. Complete your look with a sleek heel.

Fit & Features
- Three pack
- Dainty snake chain
- Mini cross charms
- Lobster clasp closure
Style Number/Barcode: 07003-0094

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tie You Down Mid-Rise Lace-Up Denim Shorts
Step into trendy fashion in these mid-rise denim shorts! The mid-rise waist and form-hugging fit accentuate your curves, while the front lace-up adds a touch of edgy style.

Fit & Features
- Light wash denim fabric, slight stretch
- Mid-rise waist, front lace-up placket
- Four-pocket styling
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-000004

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Season of Stripes Cutout Gauze Mini Dress
Keep it sassy in a striped dress this season to keep on-trend! Make a stunning impression for that upcoming date in a dress that features a plunging V-neckline, sexy bar waist cutouts, and a trendy striped design. Complete look with wedges and fringe earrings to channel bohemian vibes.

Fit & Features
- Sleeveless V-neckline
- Smocked waist
- Bar waist cutouts
- Striped pattern
- Mini length silhouette
- Gauze-linen fabric
- Form hugging fit, minimal stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0414

Category Name: Vacation Looks

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feelin' Fresh In Floral Ruffle Hem Mini Dress
Get a fresh look in this gorg floral ruffle hem mini dress! It features woven tie shoulder straps and cute ruffle detail at the hem for a fun and flirty vibe. A must-have for your next backyard bbq, style it up with clear slide on mules and sleek gold hoop earrings.

Fit & Features
- Tie shoulder straps
- Slight sweetheart neckline
- Partially smocked back with a hidden zipper closure
- Short ruffle hem
- Floral print
- Woven fabric
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0833

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Open Back Flared Skater Romper
Bring the flare in this fab romper and throw on this romper for your next GNO with the squad. The romper features a bold open back with tie back ties, spaghetti straps, and wide-leg shorts with a flared overlay that creates a skater silhouette. Complete your look with wedges and extra loop hoops.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back with tie back ties
- Wide-leg shorts
- Flared skater overlay
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06403-0128

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
The Classic Straw Floppy Hat
Step out this season with a floppy hat to give your sunkissed looks plenty of flair and style! The hat features a traditional floppy hat design with a wide brim and composed of light straw material. Complete your look with a floral sundress and cork wedges.

Fit & Features
- Traditional oversized floppy design
- Wide brim
- Straw material
Style Number/Barcode: 07302-0209

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Major Trendsetter Tie Front Crop Top
Trend alert! Impress in a tie front top that comes in a super cute print for that next happy hour with the squad! The top features a plunging v-neckline with a tie front accent, long sleeves, and a trendy geometric print. Complete your look with high waist skinny jeans.

Fit & Features
- Plunging v-neckline
- Tie-front bodice
- Cropped hem
- Long sleeves
- Geometric print
- Lightweight woven fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-0629

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Persuasion Ruched Mini Dress
Charm in a floral dress that brings major sweet appeal! Step out for your next lunch date with bae in this head-turning dress. The dress features a plunging v-neckline, quarter sleeves with a ruffled hem, a ruched center that runs bodice through the hem, and a cute floral print! Complete your look with cork wedges and sleek hoops.

Fit & Features
- Plunging v-neckline
- 3/4 sleeves with ruffled hem
- Ruched center that runs bodice through the hem
- Floral print
- Mini length silhouette with ruffled hem
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0724

Category Name: Vacation Looks

Price: $18.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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