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.

Glitzy Poolside Vibes Maxi Skirt
Showcase fab glitzy poolside vibes with this sheer mesh maxi skirt. It features a high-rise banded waist, a fitted maxi-length silhouette with a sultry thigh-high side slit, and all-over rhinestone embellishment. Style this cover-up over your fave bikini and complete the look with a floppy hat.

Fit & Features
- High-rise banded waist
- Fitted maxi-length silhouette
- High side slit
- Sheer mesh fabric
- All-over rhinestone embellishment
- Runs true to size
Style Number/Barcode: 06501-0675

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortless Boho Flair Tulip Pants
Bring that effortless boho flair to your casual summer look with these trendy tulip pants. They feature a high-rise fitted waist, a wide-leg silhouette with high front slits, a flowy, relaxed fit, and an all-over bohemian-inspired border print. Style these pants with a crop top and sandals.

Fit & Features
- High-rise fitted waist
- Wide-leg silhouette, high front slits
- Relaxed fit
- Bohemian-inspired border print
- Lightweight woven fabric
- Runs true to size
Style Number/Barcode: 06302-0657

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Vibes Wide Leg Jumpsuit
Transport to a tropical paradise with a jumpsuit that is vacay ready! The jumpsuit features a tropical floral print, a sleeveless square neckline, and a wide-leg pant. The jumpsuit is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and sunnies.

Fit & Features
- Tropical floral print
- Sleeveless square neckline
- Wide leg pant
- Sleek knit lined fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0754

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On Fleek Cat Eye Sunglasses
Nail that cat-eye trend without having to master eye liner! These sunglasses feature a classic cat-eye silhouette, plastic frame, and gradient lenses. Complete the look in a casual jumpsuit for a weekend getaway.

Fit & Features
- Classic cat-eye silhouette
- Plastic frame
- Gradient lenses
- 100% UV protection
Style Number/Barcode: 07008-0940

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Retro Getaway Mesh Mini Dress
Make sure to pack this retro-fab mini dress for your next desert getaway! It features a sleeveless crew neckline, tank shoulder straps, cinched detailing down one side with an adjustable drawstring, and a short, form-hugging fit. The sheer mesh fabric features an all-over paisley print pattern. Style this dress over the matching bikini with cat-eye sunglasses.

Shop Matching Bikini Top: Retro Getaway Bikini Top

Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms

Shop Matching Headwrap: Retro Getaway Mesh Headwrap

Shop Matching Skirt: Retro Getaway Mesh Mini Skirt

Shop Matching Duster: Retro Getaway Long Mesh Duster

Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Cinched detailing down one side, adjustable drawstring
- Mini-length, form-fitting silhouette
- Paisley print
- Sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4028

Category Name: Vacation Looks

Price: $24.90

Availability: Out of Stock
Product Badge:
- Clearance
So Extra Glam Rhinestone Bucket Hat
Elevate your festival fit in this extra glam bucket hat featuring all-over rhinestone embellishments and a short brim. Complete the look in an edgy-cute graphic tunic top.

Fit & Features
- All-over rhinestone embellishments
- Short brim
- Classic bucket hat styling
Style Number/Barcode: 07302-0642

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreamy Island Vibes Crop Top
Showcase dreamy island vibes in this lightweight chiffon crop top! It features a sleeveless square neckline, adjustable spaghetti straps for a customizable fit, a cropped, form-hugging silhouette, and an all-over tropical palm leaf print. Style this cute top with the matching kimono and shorts.

Shop Matching Kimono: Dreamy Island Vibes Chiffon Kimono

Shop Matching Bottoms: Dreamy Island Vibes Tie-Waist Shorts

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper closure
- Cropped, form-hugging fit
- Tropical palm leaf print
- Chiffon fabric
- Runs true to size
Style Number/Barcode: 06003-1608

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Dreamy Island Vibes Chiffon Kimono
Showcase dreamy island vibes in this airy chiffon kimono! It features flowy three-quarter-length kimono-style sleeves, an open front, a relaxed fit, and an all-over tropical palm leaf print. Style this lightweight layer with the matching crop top and shorts.

Shop Matching Top: Dreamy Island Vibes Crop Top

Shop Matching Bottoms: Dreamy Island Vibes Tie-Waist Shorts

Fit & Features
- Flowy three-quarter-length kimono-style sleeves
- Open front
- Relaxed fit, subtle high-low hem
- Tropical palm-leaf print
- Semi-sheer chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1224

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreamy Island Vibes Tie-Waist Shorts
Showcase dreamy island vibes in these lightweight high-rise shorts! They feature a tie-front design, a back-smocked waistband for comfortable wear, a fitted silhouette, and an all-over tropical palm leaf print. Style these cute shorts with the matching kimono and crop top.

Shop Matching Kimono: Dreamy Island Vibes Chiffon Kimono

Shop Matching Top: Dreamy Island Vibes Crop Top

Fit & Features
- High-rise waist, back-smocked waistband
- Tie-front, pleated detailing
- Fitted silhouette
- Tropical palm leaf print
- Chiffon lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06403-0206

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish And Smocked Crop Top
This smocked crop top will give your summer look a stylish vibe! It features a sleeveless V-neckline, spaghetti straps, and a cropped, form-hugging fit. Complete the outfit with the matching mini skirt and chic mules.

Shop Matching Bottoms: Stylish And Smocked Mini Skirt

Fit & Features
- V-neckline
- Spaghetti straps
- Cropped, form-hugging fit
- Smocked knit fabric
- Runs true to size
Style Number/Barcode: 06001-3287

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In Town Large Straw Floppy Hat
Heading into town? Shade yourself from the sun in style wearing this large straw floppy hat. It features a wide brim and two-tone striped design. Complete the look in a darling matching set.

Fit & Features
- Large design
- Wide floppy brim
- Two-tone striped design
- Straw material
Style Number/Barcode: 07302-0515

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Holiday In The Sun Smocked Crop Top
If ya got it flaunt it on holiday! Sass up your look in this smocked crop top featuring a sleeveless sweetheart neck, sleek elasticized spaghetti straps, and a flirty front cinch accent. Complete the look with the matching mini skirt.

Shop Matching Bottoms: Holiday In The Sun Smocked Mini Skirt

Fit & Features
- Sleeveless, sweetheart neck
- Elasticized spaghetti straps
- Front cinch accent
- Cropped hem
- Smocked fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3756

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Good At Being Bad Lace Hot Shorts
Earn style cred in these lace hot shorts with frilly ruffles and a cheeky fit. Pair with the matching top.

Fit & Features
- Lace fabric
- Low-rise waist
- Frilly ruffled design
- Cheeky fit
- Runs true to size
Shop The Matching Top: Good At Being Bag Lace Crop Top
Style Number/Barcode: 06503-000027

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: L
Product Badge:
- Sale
Holiday In The Sun Smocked Mini Skirt
If ya got it flaunt it on holiday! Sass up your look in this smocked mini skirt featuring a high-rise waist and a mini-length, curve-hugging silhouette. Complete the look with the matching crop top.

Shop Matching Top: Holiday In The Sun Smocked Crop Top

Fit & Features
- High-rise waist
- Mini-length, form-fitting silhouette
- Smocked knit-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0543

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Retro Wide-Leg Pants
Showcase a trendy retro vibe in these chic palazzo pants. They feature a high-rise smocked waist, a wide-leg silhouette, and a relaxed fit. The lightweight woven fabric features a fab all-over geometric pattern. Style with the matching bandeau top.

Shop Matching Top: So Retro Halter Bandeau Top

Fit & Features
- High-rise smocked waist
- Wide-leg silhouette
- Relaxed fit
- Geometric pattern
- Unlined woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0636

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Retro Halter Bandeau Top
Showcase a trendy retro vibe in this alluring bandeau top. It features a sleeveless halter neckline with spaghetti straps, a center O-ring accent at the bust, and a tie-back strap design. The lightweight woven fabric features a fab all-over geometric pattern. Style with the matching wide-leg pants.

Shop Matching Bottoms: So Retro Wide-Leg Pants

Fit & Features
- Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
- Center O-ring detail
- Tie-back strap design
- Cropped, form-hugging fit
- Geometric pattern
- Woven fabric, front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4123

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Retro Getaway Bikini Top
Make sure to pack this retro-fab bikini top for your next desert getaway! It features a basic triangle design with padded cups, halter spaghetti straps, and lower tie-back spaghetti straps. The top features an all-over paisley print pattern. Style with the matching bikini bottoms and cat-eye sunglasses.

Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms

Shop Matching Headwrap: Retro Getaway Mesh Headwrap

Shop Matching Skirt: Retro Getaway Mesh Mini Skirt

Shop Matching Dress: Retro Getaway Mesh Mini Dress

Shop Matching Duster: Retro Getaway Long Mesh Duster

Fit & Features
- Triangle design
- Removable padding
- Halter spaghetti straps, tie at the back of the neck
- Lower tie-back spaghetti straps
- Paisley print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0641

Category Name: Vacation Looks

Price: $20.90

Availability: Out of Stock
Product Badge:
- Sale
Tight Race Seamless Biker Romper
Stay comfy while running errands in this stylish seamless biker romper featuring a sleeveless, boat neckline, adjustable spaghetti straps, and a bodycon silhouette. Composed of stretchy rib-knit fabric. Finish the look in an oversized plaid shacket and a dad hat.

Fit & Features
- Sleeveless, boat neckline, adjustable spaghetti straps
- Biker-length shorts
- Bodycon silhouette
- Stretchy rib-knit fabric
- Seamless design for comfort
- Fits true to size
Style Number/Barcode: 07103-0750

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Natural Instinct Snake Charm Anklet
Eyeing this anklet? It must be a natural instinct of yours to like nice things! It features a two-row rhinestone design and a snake charm with a lobster clasp closure. Complete the look in a chic midi dress for your next vacation.

Fit & Features
- Two-row rhinestone design
- Snake charm
- Lobster clasp closure
Style Number/Barcode: 07003-0334

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
When In Floral Chiffon Smocked Crop Top
When in floral, flaunt it! Create a cute look in this chiffon crop top featuring long peasant sleeves, a ruffled sweetheart neckline, and a smocked bodice with ruched tie closure. Complete the look in jeans and heels.

Fit & Features
- Long peasant sleeves
- Ruffled sweetheart neckline
- Smocked bodice, ruched tie closure
- Floral pattern
- Chiffon fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1686

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Days Polka Dot Jumpsuit
This breezy lightweight jumpsuit is perfect for casual summer days! It features a sleeveless V-neckline, spaghetti straps, a partially open back with an adjustable tie closure, and an on-trend, flowy, wide-leg fit. The airy woven fabric features an all-over adorable polka dot print. Complete the outfit with espadrille sandals.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Partially open back, adjustable tie closure, hidden zipper, hook and eye closure
- Relaxed wide-leg fit
- Polka dot print
- Woven fabric, short woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06302-0652

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Shades For Days Round Sunglasses
The perfect sunglasses for wearing on rotation! They feature a sleek plastic round frame, gradient lens, and side metal accents. Complete the look in a swim cover-up and swimsuit for the perf beach fit.

Fit & Features
- Sleek plastic round frames
- Gradient lens
- Side metal accents
- 100% UV protection
Style Number/Barcode: 07008-0966

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All Day Slay Square Ombre Sunglasses
Slay all day in these cool sunglasses featuring a sleek square metal frame, ombre tint gradient lens, and rubber nose support for comfort. Complete the look in a classic denim jacket for running errands.

Fit & Features
- Sleek square metal frame
- Ombre tint gradient lens
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-0964

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sea Breeze Tropical Midi Dress
Take a sunset stroll in this alluring tropical midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched detailing down one side, and a midi-length, asymmetrical hem creating a high side slit. The all-over palm leaf print will bring major vacay vibes. Style with strappy sandals and a flowy kimono.

Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruching down one side
- Midi-length, asymmetrical hem, side slit
- Curve-hugging silhouette
- Palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4421

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials