Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

Make It Slay 50/50 Stiletto Boots
Make every outfit slay with these stiletto boots featuring a sleek pointed toe, side zipper closure, a knee-high shaft length, and a 50/50 faux leather and scuba knit material. Style with a longline coat for a dinner in the city!

Fit & Features
- Pointed toe
- Stiletto heel
- Side zipper closure
- Knee-high shaft length
- 50/50 faux leather, scuba knit material
- Runs true to size
Style Number/Barcode: 07402-0802

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortlessly Elevated Strapless Linen-Blend Dress
Effortlessly elevated, this breezy linen-blend dress is such a summer staple. It features a strapless straight-across neckline, a secure back zipper closure, a ruched fitted high waist, hidden side pockets, and a flowy A-line mid-length silhouette for that relaxed casual-chic vibe. Style with espadrille sandals.

Fit & Features
- Linen-blend fabric
- Strapless straight neckline
- Back zipper hook-eye closure
- Ruched high waist
- Side pockets
- A-line fit, mid-length hem
- Runs true to size
Style Number/Barcode: 05102-5823

Category Name: Vacation Looks

Price: $20.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feeling Peachy Graphic Tube Top
Made for sunny day dressing, this graphic tube top showcases a front peach and graphic detailing that creates boldly cute looks!

Fit & Features
- Stretchy knit fabric
- Strapless neckline
- Peach and graphic detailing
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000035

Category Name: Vacation Looks

Price: $22.90

Availability: In Stock

Available Color: ORANGE

Available Size: L
Groovy Gal Striped Cutout Mini Dress
When your dress is the moment, this one’s got that groovy energy! The bold bell sleeves and plunging neckline were made for concerts, bright lights, and dance floors.

Fit & Features
- Striped texture knit fabric, soft stretchy knit lining
- Plunging V-neckline with half hoop insert
- Bell long sleeve
- Side cutouts and open back
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000118

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: MULTI

Available Size: XS, S, M, L
Made For Struts Over The Knee Boots
Made for stylish strutting down the street, you'll adore these faux leather over-the-knee boots featuring an almond toe, a stacked block heel, a side zipper closure, and a high shaft. Complete the look in a trendy sweater dress for a day in the city!

Fit & Features
- Almond toe
- Stacked block heel
- Side zipper closure
- High shaft, over the knee
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0843

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendsetting Vibe Lace-Up Denim Shorts
Show off a trendsetting vibe in these mid-rise denim shorts for festival season! The lace-up side design adds the perfect edge to your casual 'fits.

Fit & Features
- Denim fabric, moderate stretch
- Mid-rise waist, belt loops
- Front button and hidden zipper closure
- Lace-up side design
- Fitted
- Runs true to size
Style Number/Barcode: 06603-0472

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: OLIVE

Available Size: L, XL
Sleek Strut Knee-High Boots
This fall season, strut with style in these sleek knee-high boots! They feature a pointed toe, a sturdy block heel, an inner zipper closure, and a fitted shaft. Pair these faux leather boots with your favorite sweater dress.

Fit & Features
- Knee-high length
- Pointed toe
- Block heel
- Inner zipper closure
- Fitted shaft
- PU material, smooth lining
- Runs true to size
Style Number/Barcode: 07402-0793

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Example Tie-Front Lace Trim Crop Top
You'll be giving off plenty of sweet and sexy vibes in this crop top! Featuring delicate cap sleeves, a flattering lace trim scoop neckline, and dual tie-front closures, this crop top effortlessly adds a touch of romance to any outfit. Complete the look in denim jeans for any casual plans!

Fit & Features
- Rib knit fabric, moderate stretch
- Cap sleeves
- Lace trim scoop neckline
- Dual tie-front closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-0476

Category Name: Vacation Looks

Price: $24.90

Availability: In Stock

Available Color: WHITE

Available Size: XS, S, M, L
Fleece Shaper Leggings
Comfy and flattering, these fleece leggings are perfect for lounging, traveling, and the office! They feature a high-waist fit with tummy control to smooth and shape your figure. These fleece-lined leggings will keep you cozy while appearing incredibly chic paired with an elevated crop top and tailored blazer or moto jacket for a fierce #OOTD look.

Fit & Features
- Tummy control waistband
- Skinny leg fit
- Cozy fleece-lined knit fabric
- Moderate stretch
- Sizes run small
Style Number/Barcode: 06502-1228

Category Name: Vacation Looks

Price: $6.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dinner And Drinks Halter Ruffle Romper
Create sultry flair in this halter ruffle romper for your next date night or GNO! This romper is designed to show off with a plunge halter neckline and a short ruffled hem.

Fit & Features
- Smooth knit stretchy fabric
- Plunge halter neckline with button closures
- Partial open back
- Ruffled short-length hem
- Shorts lining
- Runs true to size
Style Number/Barcode: 06503-1279

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Stylish Staple Henley Crop Top
This on-trend henley crop top is a stylish staple to add to your cart! It features a scoop neckline with a plunging notched front design, sleek metal grommet accents, long fitted sleeves, a fitted cropped hem, and a lower back cutout with a criss-cross strap design. Pair this ribbed knit top with cargo pants and mules.

Fit & Features
- Scoop neckline, plunging notched front design
- Metal grommet accents
- Long fitted sleeves
- Fitted cropped hem
- Lower back cutout, criss-cross strap design
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1495

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Festive Fun High-Rise Striped Palazzo Pants
Weekend activities just got a little cuter in these striped palazzo pants perfect for vacations or going to a summer fair! The high-rise elasticized waistband and pleating create a comfortable and flattering fit, while the wide-leg flowy silhouette and striped print bring a stylish touch. Complete the look with the matching top

Shop The Matching Top: Festive Fun Strapless Striped Bandeau Crop Top

Fit & Features
- Striped print, woven fabric
- High-rise elasticized waistband with pleating
- Wide-leg flowy silhouette
- Runs true to size
Style Number/Barcode: 06402-1424

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Enchantment Floral Pleated Maxi Dress
This floral maxi dress brings the effortless, enchanted vibes to any occasion! With a sweetheart neckline and a pleated, flowy silhouette, you'll adore this dress all season long.

Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline
- Adjustable spaghetti straps
- Tie-back detail, lower hidden zipper and hook-eye closure
- Pleated flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3914

Category Name: Vacation Looks

Price: $26.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Serving Shade Square Oversized Sunglasses
These oversized square sunglasses with tinted lenses = instant it-girl upgrade!

Fit & Features
- Oversized square frames
- Tinted 100% UV protection lenses
- Smooth plastic frame with luxe finish
Style Number/Barcode: 07008-000007

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: NUDE

Available Size: NS
Cozy Prep Collared Sweater
Cozy on up this fall while still keeping your look preppy with this cute collared sweater. It features a V-neckline with a trendy polo collar, long dolman-style sleeves, and a mid-length, relaxed fit. The soft ribbed knit fabric offers a moderate stretch for comfortable wear. Style this sweater with dark wash denim and booties.

Fit & Features
- V-neckline
- Polo collar
- Long dolman sleeves, tapered hems
- Mid-length, relaxed fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1300

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Ready Strapless Knit Tube Top
A summer-ready staple, this knit tube top boasts a flirty cutout accent and a cropped hem perfect for styling with high-rise bottoms!

Fit & Features
- Sweater knit fabric
- Strapless neckline
- Cutout design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-2301

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Destination Dinner V-Neck Midi Dress
Look fabulous in a flash wearing this sleeveless midi dress for dinner and drinks! It features a showstopping bodycon silhouette, a V-neck, tank straps, and side ruched seams that hug every curve like a glove. Complete the look with chic stiletto heels.

Fit & Features
- Sleeveless, V-neck, tank straps
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Slinky knit fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4834

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunny Oasis Halter Crop Top
Escape to a sunny destination with this alluring halter cowl crop top! Pair with the matching skirt to complete the trendy vibe.

Fit & Features
- Slinky knit stretchy fabric
- Halter cowl neckline, tie closure
- Side ruched seams
- Crop hem
- Runs true to size
Shop The Matching Skirt: Sunny Oasis Ruffle Mini Skirt
Style Number/Barcode: 06001-000145

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: In Stock

Available Color: YELLOW

Available Size: S, M, L
Product Badge:
- Sale
Slinky Knit Wrap Front Top
The perf dressy top to take you from the office to happy hour. It features bishop long sleeves, a plunge V-neckline, and a wrap-style bodice, with tie-front detail along the cropped hem. Complete your look with high-rise pants and heels.

Fit & Features
- Bishop long sleeves
- Plunge V-neckline
- Wrap-style bodice
- Tie-front detail, crop hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06001-4708

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Getaway Retreat Sweetheart Tropical Crop Top
Getaway in this tropical crop top for the sweetest vacay vibe! This crop top features wide shoulder straps, a sweetheart neckline for a flattering look, padded bra cups for support, and a stretchy smocked back and cropped hem to flaunt your figure. Complete the look with the matching bottoms.

Shop The Matching Bottoms: Getaway Retreat High Rise Tropical Pants

Fit & Features
- Tropical print, woven fabric, sewn-in lining
- Wide shoulder straps
- Sweetheart neckline
- Padded bra cups
- Stretchy smocked back
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2504

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Bloom Floral Mesh Maxi Skirt
Serve a sultry vibe in this blooming floral printed mesh maxi skirt! Designed with ruched side seams to show off your curves, style with the matching tube top for a gorgeous look.

Shop Matching Top: Sultry Bloom Floral Mesh Tube Top

Fit & Features
- Sheer mesh fabric with full-length knit lining, high stretch
- Floral print
- High-rise waist
- Maxi-length hem, lettuce-edge trim
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-1142

Category Name: Vacation Looks

Price: $24.90

Availability: In Stock

Available Color: MAGENTA

Available Size: S, M
Product Badge:
- Part of a Set
Little Miss Charming Strappy Back Denim Romper
Turn heads with your charm in this denim romper at concerts or weekend fun! Designed with a strappy open back, side pockets, and a pleated short hem, this romper is both stylish and functional.

Fit & Features
- Denim fabric
- Halter V-neckline, keyhole cutout
- Strappy open back, zipper closure
- Side pockets
- Pleated short hem
- Runs true to size
Style Number/Barcode: 06603-000008

Category Name: Vacation Looks

Price: $46.90

Availability: In Stock

Available Color: DENIM

Available Size: S
Chic Flowy Chiffon Midi Dress
Get the perf semi-formal look in this effortlessly chic chiffon midi dress. It features a sleeveless sweetheart neckline with a padded bust, spaghetti straps, a flattering high waist seam, and a mid-length skirt with a front slit and a flowy A-line silhouette. Style this dress with sleek earrings and cute heels.

Fit & Features
- Sleeveless sweetheart neckline
- Built-in padded bust
- Adjustable spaghetti straps
- Partially smocked back, zipper and hook-eye closure
- High waist seam, flowy A-line silhouette, front slit
- Sheer chiffon fabric, inner knit lining
- Runs true to size
Style Number/Barcode: 05101-2187

Category Name: Vacation Looks

Price: $5.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Style Ruched Romper
Show off your flirty style in this adorable romper! Designed with a stretchy smooth knit fabric, it features a sweetheart neckline, short puff sleeves that can be worn off-the-shoulder, ruched detailing at the waist, a fit and flare silhouette, and flowy shorts with a mini skirt overlay. Complete the look with gold hoops and strappy sandals.

Fit & Features
- Smooth knit fabric, plenty of stretch
- Sweetheart neckline
- Short puff sleeves, elastic cinched hems
- Ruching at the waist, elastic seams
- Fit and flare silhouette
- Flowy shorts, mini skirt overlay
- Runs true to size
Style Number/Barcode: 06503-0987

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials