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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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.

Love's In The Air Floral Chiffon A-Line Dress
Slip into the romantic vibes of this floral chiffon mini dress for day dates to shower celebrations! The dress flaunts a pretty corset bodice and lace-up back that turns heads, while the A-line silhouette flatters your figure.

Fit & Features
- Dainty floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05101-4046

Category Name: Vacation Looks

Price: $9.97

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Touch Faux Wool Beret
This beret will add a chic touch to all of your 'fits this season! It features a classic beret design and is composed of a faux wool material. Style with an oversized blazer and ankle booties for a city trip!

Fit & Features
- Classic beret design
- Faux wool material
- Moderate stretch
Style Number/Barcode: 07302-1486

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Influence Strapless Bodycon Midi Dress
Achieve a stylish rep in this strapless midi dress wherever you go! With a flattering bodycon fit and trendy stone metal insert, this dress will enhance your natural silhouette and captivate any room you enter.

Fit & Features
- Stretchy knit fabric
- Strapless neckline, stone metal insert
- bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000062

Category Name: Vacation Looks

Price: $19.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Softest Style Plaid Frayed Scarf
This plaid frayed scarf will be the softest style in your lineup! Perfect for wearing around your neck or shoulders, the styling possibilities are endless. Complete the look in cute boots.

Fit & Features
- Plaid pattern
- Frayed edge trim
- Ultra-soft knit material
Style Number/Barcode: 07305-0459

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Escape Cropped Halter Top
Shop Matching Bottoms: Coastal Escape High Rise Ruched Midi Skirt

Fit & Features
- Smooth knit fabrication
- Sleeveless halter neckline
- Halter neck ties
- Cutouts
- Beaded detailing
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5672

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cold Weather Luxe Faux Fur Trim Gloves
Enter into the cold season with luxe style with these faux fur gloves! They feature a fitted design made from soft faux suede material with chic faux fur cuffs. Complete your cute cold-weather 'fit with a rhinestone-embellished beanie!

Fit & Features
- Fitted design
- Faux suede fabric
- Faux fur cuffs
Style Number/Barcode: 07304-000007

Category Name: Vacation Looks

Price: $16.90

Availability: In Stock

Available Color: BLACK-2

Available Size: NS
Product Badge:
- Best Seller
Feelin' Bold Floral Mesh Strapless Maxi Dress
Be a bold babe in this airy mesh maxi dress designed with a large floral print pattern to turn heads. Featuring ruching at the bust, a high-cut side slit, and a form-hugging silhouette, style with wedges for a sunset dinner.

Fit & Features
- Sheer mesh fabric with full-length brushed knit lining, high stretch
- Large floral print
- Strapless straight-across neckline
- Ruched bust
- Thigh-high side slit
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000098

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
My Lane Corduroy Faux Sherpa Collar Crop Jacket
Take a walk down style lane in this corduroy crop jacket essential for the chilly season ahead! It features long sleeves with button cuffs, a faux sherpa collar, button-down front and flap pockets, and a back elasticized cinch hem. Layer over a basic top and currently trending cargo pants.

Fit & Features
- Long sleeves, button cuffs
- Faux sherpa collar
- Button down front, flap pockets
- Cropped hem
- Back elasticized cinch hem
- Corduroy fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1690

Category Name: Vacation Looks

Price: $15.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Escape Floral Slit Maxi Skirt
Giving off total romantic vibes, this floral maxi skirt is flirty without trying too hard. With a high-rise waist, curve-hugging fit, and a high side slit detail, it’s the perfect blend of dreamy and effortless.

Fit & Features
- Floral print, mesh-lined fabric
- High-rise waist
- Curve-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000065

Category Name: Vacation Looks

Price: $11.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK-2

Available Size: S, M
Product Badge:
- Sale
Such A Daydream Chiffon Crop Top
You'll look like such a daydream in this airy chiffon crop top! It features a subtle sweetheart neckline, a ruched bust, long sheer bishop sleeves, a cropped hem with a wrap-front detail, and a stylish tie-back design. Complete the look with cute denim and clear mules.

Fit & Features
- Sheer chiffon fabric, front knit lining, minimal stretch
- Sweetheart neckline
- Ruched bust
- Long sheer bishop sleeves, elastic cinched hems
- Cropped hem, wrap-front detail
- Tie-back design
- Runs true to size
Style Number/Barcode: 06003-2301

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On Repeat Flat Over-The-Knee Boots
These must-have flat over-the-knee boots will be styled on repeat all season long. They feature a fitted over-the-knee design, an inner zipper closure that runs down the length of the boot, an almond-shaped toe, and a flat sole with a short block heel. The boots have a trendy design of sleek faux leather at the front with smooth spandex at the back. Pair with a sweater dress for such a chic winter look.

Fit & Features
- Fitted over-the-knee design
- Complete inner zipper closure
- Almond toe
- Flat sole, short block heel
- Half faux leather material
- Half lycra material
- Runs true to size
Style Number/Barcode: 07402-0980

Category Name: Vacation Looks

Price: $11.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Babe Knit Cutout Tube Top
Channel a boho babe vibe in this sweater knit tube top featuring a strapless straight neckline, dual bust cutouts with a beaded trim, and a front slit accent. Style with the matching mini skirt for a chic and seamless look!

Shop Matching Bottoms: Bohemian Babe Knit High-Rise Mini Skirt

Fit & Features
- Sweater knit fabric, ribbed hems, high stretch
- Strapless straight-across neckline
- Dual bust cutouts, beaded trim
- Front slit design
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06005-000031

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Gimme The Flare Denim Jumpsuit
Give your closet a trendy upgrade in this essential denim jumpsuit perfect for hitting up the farmer's market or grabbing brunch with friends! It features short sleeves, a collar neckline, button-down front closures, four-pocket styling, belt loop accents, and a hip-hugging flare-leg silhouette. Complete the look in peep toe booties.

Fit & Features
- Short sleeves
- Collar neckline
- Button-down front closures
- Four-pocket styling, belt loop accents
- Hip-hugging, flare-leg silhouette
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0366

Category Name: Vacation Looks

Price: $6.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Chic Straw Platform Block Heels
Platform and boho chic, these block heels were made for fun under the sun! Pack these essential shoes for vacations, weekend trips, or a beach day. They feature an almond toe, an adjustable ankle strap with buckle closure, and a platform sole to elevate the style. Complete the look with the matching hat and bag!

Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote Bag

Fit & Features
- 3.5" Block heel
- Almond toe
- Adjustable ankle strap, buckle closure
- Platform sole
- Luxe fit cushioned insole
- Straw material
- Runs true to size
Style Number/Barcode: 07401-4659

Category Name: Vacation Looks

Price: $20.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Irresistibly Sweet V-Neck Floral Chiffon Maxi Dress
You'll be irresistibly sweet in this floral chiffon maxi dress at showers, graduations, or semi-formal events! The V-neckline and spaghetti strap tie accentuate your frame while the flowy maxi silhouette adds a touch of elegance. With a front slit and floor-length hem, this dress is perfect for any occasion. Complete the look in espadrille wedges.

Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- V-neckline
- Spaghetti strap ties
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3301

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Mood Rectangle Sunglasses
Top off your summer 'fits and bring that bold flair with these trendy rectangle sunglasses! These cool shades feature a rectangular-shaped design with a thick plastic frame, wide arms, built-in nose pads, and tinted lenses. Style with strappy sandals.

Fit & Features
- Rectangular-shaped design
- Thick plastic frame
- Wide arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1077

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Get Cutesy Faux Leather Sherpa Bucket Hat
Get cutesy with your outfit in this faux leather bucket hat perfect for bringing the cozy vibes! The hat features a classic bucket hat styling with a faux sherpa trim. Complete the look in a cozy jacket on a chilly day!

Fit & Features
- Faux leather exterior
- Classic bucket hat styling
- Faux sherpa trim
Style Number/Barcode: 07302-1488

Category Name: Vacation Looks

Price: $3.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Mode Cotton Bra Top
Activate summer mode with this lightweight cotton bra top featuring a sleeveless V-neckline, adjustable spaghetti straps, and a fitted ultra-cropped hem. Style with the matching button-down top and high-rise shorts for an effortlessly chic look.

Shop Matching Set: Summer Mode Button-Down Cotton Top, Summer Mode High-Rise Cotton Shorts

Fit & Features
- Textured cotton fabric
- Sleeveless V-neckline, surplice design
- Adjustable spaghetti straps
- Stretchy smocked back
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06003-000082

Category Name: Vacation Looks

Price: $22.90

Availability: In Stock

Available Color: CHARTREUSE

Available Size: S, M, L
Product Badge:
- Part of a Set
Posh And Pretty Strapless Bow Ponte Crop Top
You'll draw everyone will this posh and pretty ponte crop top! Designed with a sleek strapless neckline and front bows with cutouts, this top will turn heads.

Fit & Features
- Ponte knit fabric
- Strapless neckline
- Front bows with cutouts
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000124

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Quite A Bell Sleeve Crop Sweater
Your new favorite crop sweater to create all sorts of trendy outfits! It features long bell sleeves, a mock neck, and a center front slit accent, and is composed of a rib-knit fabric with minimal stretch. Style with flare denim jeans to complete the look.

Fit & Features
- Long bell sleeves
- Mock neck
- Center front slit accent
- Cropped hem
- Sweater rib-knit fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1812

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Simply Sunny Scoop Neck Skater Eyelet Mini Dress
Sunshine days are ahead and this skater mini dress is perfect for enjoying the weekend and weather! Crafted from an adorable eyelet knit fabric, this mini dress is designed with a flattering scoop neckline, adjustable spaghetti straps for a perfect fit, and a flirty tie-back detail to show off your style. The skater silhouette and tiered ruffled hem allow for movement and a fashionable sway with every step! Complete the look in heeled sandals.

Fit & Features
- Eyelet knit fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Tie-back detail
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5426

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Style Woven Tie-Waist Wide-Leg Pants
Capture that coastal-chic style with these breezy tie-waist wide-leg pants. Designed with an airy lightweight woven fabric, they feature a high-rise waist with an elasticized back waistband for added stretch, a side tie accent, and a flowy wide-leg silhouette. Pair with a basic crop top and strappy sandals.

Fit & Features
- Airy woven fabric, no stretch
- High waist, elasticized back waistband
- Side tie detail
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06402-1409

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Traveling Cute Halter Wide-Leg Cargo Jumpsuit
Travel cute wherever you're heading in this sleeveless woven jumpsuit for a chic and polished vibe! The halter collar neckline and front zipper closure provide a classic and utility touch, while the open back with an adjustable strap flaunts some skin, and side and flap pockets offer functionality along the wide-leg silhouette. Complete the look with a trendy shoulder handbag.

Fit & Features
- Woven fabric
- Front zipper closure
- Open back, adjustable strap
- Side pockets, flap pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1407

Category Name: Vacation Looks

Price: $24.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Now In Bloom Open Back Floral Maxi Dress
A sultry open back you'll adore with chic floral blooms! This maxi dress captures attention with its flattering cowl neckline and curve-hugging silhouette, perfect for shower celebrations and dressy events!

Fit & Features
- Floral print, mesh-lined fabric
- Cowl neckline
- Spaghetti strap ties
- Open back
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000023

Category Name: Vacation Looks

Price: $19.97 $44.90

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