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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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.

Ruffled Floral Mini Dress
This ruffled floral mini dress couldn't be more spring-ready! It features an off the shoulder sweetheart neckline with light padding and a ruffle overlay, a high waist seam, and a short, form hugging fit. The ivory dress is composed of a scuba knit fabric that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8713

Category Name: Vacation Looks

Price: $10.00 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Lace High Low Dress
Embrace a fresh spring vibe with pretty florals! This light blue dress features a plunging V neckline, princess seams, narrow straps and an unlined floral lace detail. The slim fit bodice leads to a flared high-low skirt to create a twirl worthy moment. The floral print features peach and white hues to complement the blue background. Dress is composed of a scuba fabric that offers a form hugging fit.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

Style Number/Barcode: 05101-0058

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fab In Floral Lace Back Mini Dress
Look your absolute best in this fab light blue floral mini dress! It features a plunging V neckline, spaghetti straps that lead to a partially exposed lace back with a zipper closure, and a form hugging bodycon fit. Crepe fabric offers moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

Style Number/Barcode: 05101-8813

Category Name: Vacation Looks

Price: $10.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Blossom With Beauty Bodycon Dress
Let your beauty blossom with this beyond gorg bodycon dress! It features a sleeveless bodice, a V neckline, spaghetti straps that lead to a sheer lace back with an exposed zipper closure, a back cut out, a high waist seam, and a short, form hugging fit. The black dress is composed of a scuba knit fabric that offers moderate stretch and showcases an all over floral print with hues of pink, green, and ivory.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8812

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Add Some Flair Skater Dress
Add some flair to your style with this adorable lace skater dress! It features an off the shoulder neckline with a sheer lace overlay, a high waist seam, and a flowy skater skirt with a high low hem. The dress is composed of a sheer lace fabric with a full knit lining and has moderate stretch.

Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

*Also available in Plus

Style Number/Barcode: 05101-8732

Category Name: Vacation Looks

Price: $18.97 $47.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Fly Abstract Slit Crop Top
Bring the heat in this abstract slit crop top! Featuring a front slit with hoop insert and an eye-catching abstract print, this top will make you stand out in any crowd.

Fit & Features
- Abstract print, knit fabric
- Strapless neckline
- Front hoop insert and slit
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000114

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Days Skater Dress
Make today a gorgeous one in charming florals! This ivory dress features a plunging wired V neckline with lined padded cups, a double row of narrow straps, a lattice back design and a flared skater skirt. The all over floral print features blush pink and lavender hues. The dress is composed of a scuba knit fabric that offers 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: 05101-8706

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spring With Florals Maxi Dress
Step out this season in pretty florals to make a charming impression! The ivory maxi dress features an off the shoulder neckline with the off the shoulder strap accents, a straight bust, a cinching tie waist belt and maxi length silhouette with a high side slit. The back features a lower back keyhole. The all over floral print features pink hues. Dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Includes an additional mini skirt length lining.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

Style Number/Barcode: 05101-8699

Category Name: Vacation Looks

Price: $19.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Skye Chiffon High Low Skater Dress
Special Occasion
Skye is airy, angelic, and will feel like you're walking on cloud 9! She features a slim fitting bodice with a V neckline, narrow shoulder straps that lead to a sheer lace back and a gold zipper closure, a banded waist, and a flowy, wrap, high-low skater skirt with a short skirt lining. Skye is composed of a light blue chiffon fabric with no stretch.
Model is 5'8" with a 32" bust, 23" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8679

Category Name: Vacation Looks

Price: $10.00 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Vibes Floral Skater Dress
This ivory skater dress is a perfect, soft vision of spring. It features a square neckline, adjustable spaghetti straps that lead to a sheer lace back and zipper closure, a high waist seam, and a fitted bodice that leads to a short flowy skirt. Dress is composed of a stretchy scuba fabric with an all over ivory and blush floral print.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05101-8683

Category Name: Vacation Looks

Price: $10.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Day Dream Midi Dress
You'll be too good to be true in this gorgeous light blue midi dress. It features a V neckline, spaghetti straps that lead to a cowl back, a knit lining, a form hugging silhouette and a below the knee length. Knit fabric features a pink hued floral print, and plenty of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8667

Category Name: Vacation Looks

Price: $10.00 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
What's Up Buttercup Maxi Dress
You're lookin' like a ray of sunshine in this mustard yellow maxi dress! It has an off the shoulder neckline with draped ruffle sleeves, a high waist seam with a tie belt and back cut out, and a flowy, floor-length wrap skirt that creates a high leg slit. Dress is composed of a gauze fabric. Includes exposed back zipper closures and a short knit lining.
Model is 5'8" with a 32" bust, 24.5" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8658

Category Name: Vacation Looks

Price: $10.00 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty & Proper Lace Midi Dress
Sit pretty and proper in this ivory lace midi dress! It features a sleeveless bodice with a mock neckline, a hidden back zipper closure, and a body-hugging fit. Dress has a full lining and is composed of a a stretchy lace fabric.
Model is 5'7" with a 34" bust, 24" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8642

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wrapped In Pleats Midi Dress
Wrap yourself in pretty pleats to make a gorgeous appearance! The mini dress features a sage green color, a wrap V neckline, narrow shoulder straps and an asymmetrical wrap silhouette. Dress is composed of a crepe fabric that offers a form hugging fit with a moderate stretch. Includes a back zipper closure.
Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05101-8615

Category Name: Vacation Looks

Price: $10.00 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Crochet Beauty Mini Dress
You're a total beauty, so showcase your stunning style in this crochet mini dress!

Fits & Features
- Adjustable Spaghetti Straps
- V Neckline & Back
- Scalloped Hem
- Fully Lined, Sheer Crochet Composition
- Form Hugging Fit
- Plenty Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-8534

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Glitz & Glam Lace Skater Dress
This fun skater dress is all about glitz and glam!

Fits & Features
- Plunging V Neckline I Padded Bust
- Spaghetti Straps
- Sheer Lace Back With Zip Closure
- High Waist Seam
- Short Flowy Skirt With Double-Tiered Hem
- Glitter Lace Composition I Fully Lined
- Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-8507

Category Name: Vacation Looks

Price: $22.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Feels Skater Dress
Get all the floral feels with this gorgeous printed skater dress! It features a sleeveless bodice, spaghetti straps that lead to a sheer lace back with an exposed gold zipper closure, a back cut out, and a flowy high low hem. The navy blue dress is composed of a scuba fabric with moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05101-8471

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty And Picturesque Skater Dress
Hello gorgeous! You'll look pretty and picturesque in this floral printed skater dress! It features an off the shoulder sweetheart neckline, short sleeves, a back zipper and hook and eye closure, a high waist seam, and a flowy skater skirt. The mauve dress is composed of a knit fabric with moderate stretch and a fitted and flowy fit.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05101-8221

Category Name: Vacation Looks

Price: $10.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chasing Dreams Ruffle Dress
Chase your dreams in this flowy blue ruffle dress! It features an off the shoulder neckline with a ruffle pop over, a fitted bodice with a high waist seam and tie belt detail, a hidden side zipper closure, and a flowy skirt with a double-tiered, high-low hem. Dress is composed of a woven fabric with no stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05101-8202

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
New Babe Strapless Slit Abstract Crop Top
Elevate your babe status in something new! This strapless abstract crop top is designed to flaunt your figure and style with a trendy slit and asymmetrical hem.

Fit & Features
- Abstract print, knit fabric
- Strapless neckline
- Side slit with tie and hoop insert
- Asymmetrical crop hem
- Runs true to size
Style Number/Barcode: 06001-000115

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Passionate About Florals Maxi Dress
Show your passion for pretty florals in this captivating maxi dress! It features a navy blue hued smocked bodice with a sweetheart neckline and leads to a sweeping maxi length silhouette. The skirt features a head turning floral print with coral and blue hues that contrast with the ivory hued background. Dress is composed of a combination smock and chiffon knit fabric that offers a relaxed fit.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8178

Category Name: Vacation Looks

Price: $10.00 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Painted In Florals Midi Dress
Radiate a romantic aura in soft water colored florals! This midi length dress has an off the shoulder neckline with an elastic hem and short sleeves. Paint yourself in the gorgeous blue and mauve colored blossoms that are complimented with green foliage. Dress is composed of a soft the touch sturdy knit fabric that offers a curve hugging fit with moderate stretch.

Model is 5'7 with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-7384

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweetly Chic Midi Dress
Have a sweetly chic look with this gray houndstooth print midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a hidden back zipper and hook and eye closure, a high waist seam, a front slit with a drawstring, and an asymmetrical hem. The dress is composed of a sheer lightweight woven fabric with a short white knit lining.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05101-0040

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fleur Floral Chiffon Dress
Special Occasion
Keep the romantic florals going in our navy blue Fleur chiffon dress. She features a plunging V neckline, a plunging V back that leads to a hidden zipper closure, a high waist seam with a tie back belt, and a wrap bodice. Long, floor-length skirt offers a flowy fit and includes a short skirt lining. Dress is composed of a semi-sheer floral chiffon fabric with no stretch.
Model is 5'6.5 with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.

Style Number/Barcode: 05002-6767

Category Name: Vacation Looks

Price: $29.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks