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.

Summer Blend Crochet Knit Top
Sun's out, shoulders out! This crochet knit top is perfect for summer festivals and casual beach days. It features a sleeveless, square neck, adjustable spaghetti straps, and a cropped hem. Complete the look in the matching top.

Shop Matching Bottoms: Summer Blend Crochet Knit Shorts

Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Cropped hem
- Crochet knit striped pattern
- No stretch
- Runs true to size
Style Number/Barcode: 06005-1502

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Chic Linen Mini Skirt
Create a casually chic impression with a mini skirt that is perf for every day! The skirt features a high-rise waist, a side lattice accent, and a short-length hem. The skirt is composed of a linen fabric that offers a relaxed fit with minimal stretch. Complete look with a crop top and heels.

Fit & Features
- High rise waist
- Side lattice accent
- Short length hem
- Linen fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06301-0115

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Glam Floral Maxi Skirt
Channel a glam vibe with a skirt that is perf for that getaway! The skirt features an elastic high-rise waist, a tropical floral with palm leaf print, and a maxi length accented with a high-side slit. Complete look with the matching tie front top!

Shop Matching Top: Tropical Glam Tie Front Top

Fit & Features
- High rise waist
- Tropical floral and palm print
- Maxi length
- High side slit
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0606

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fierce And Fine Triangle Bikini Top
You'll be looking so fierce and fine in this minimal bikini top. It features a classic triangle design with halter spaghetti straps and tie-back straps and an all-over leopard print pattern. Style with the matching bikini bottoms and a sheer flowy duster.

Shop Matching Bottoms: Fierce And Fine Thong Bikini Bottoms

Fit & Features
- Triangle design
- No padding
- Halter spaghetti straps, tie at the back of the neck
- Tie-back straps
- Leopard print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0685

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend Muse Square Sunglasses
Serving low-effort luxe from sunrise to happy hour. These square sunglasses give effortless it-girl vibes with a sleek metal frame that pairs with everything from linen sets to poolside 'fits.

Fit & Features
- Curved square-shaped design
- Thin metal frame
- Thin arms
- Flexible nose pads
- Tinted lenses
Style Number/Barcode: 07008-000055

Category Name: Vacation Looks

Price: $5.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Dreamy Daisy Printed Swim Top
You'll look like a total daydream in this adorable daisy printed swim top! It features a convertible bandeau fit with spaghetti straps you can tie in a halter style, a cross-front design, as a one-shoulder neckline, or as a cute bralette. Style with the matching swim bottoms and some retro sunnies.

Shop Matching Bottoms: So Dreamy Daisy Printed Swim Bottoms

Fit & Features
- Convertible bandeau fit
- Spaghetti straps
- No padding
- Daisy print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0681

Category Name: Vacation Looks

Price: $4.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine On My Mind Swim Tank
You'll be ready for a beach day with the girls with this cute and bright swim tank. It features a V-neckline with a twist-front design and adjustable tank shoulder straps for a customized fit. Style with the matching swim bottoms and your fave shades.

Shop Matching Bottoms: Sunshine On My Mind Swim Bottoms

Fit & Features
- V-neckline
- Twist-front design
- Adjustable tank shoulder straps
- Runs true to size
Style Number/Barcode: 07104-0640

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Country Club Rhine Straw Floppy Hat
Meet up with the ladies at the country club looking glam in this straw floppy hat. It features a rhinestone embellished trim, a wide brim, and classic styling. Complete the look in a posh midi dress and heels.

Fit & Features
- Rhinestone embellished trim
- Wide brim
- Floppy silhouette
- Classic styling
- Straw material
Style Number/Barcode: 07302-0501

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Essential Straw Visor
Shield your tresses with a straw visor that is perf for those summer days! The visor features a traditional visor design with a wide brim and velcro straps to secure the visor. Complete your look with a matching crop top and maxi skirt.

Fit & Features
- Traditional visor design
- Wide brim
- Velcro straps
Style Number/Barcode: 07302-0517

Category Name: Vacation Looks

Price: $8.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wild At Heart Strappy Bikini Top
You'll fall head over heels for this adorable bikini top! It features a triangle design with a center metal heart accent, halter spaghetti straps, and a trendy wrap-around strappy design. Style with the matching bikini bottoms.

Shop Matching Bottoms: Wild At Heart Strappy Bikini Bottoms

Fit & Features
- Triangle design
- Center metal heart accent
- Halter spaghetti straps, tie at the back of the neck
- Wrap-around strappy design
- Removable padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0683

Category Name: Vacation Looks

Price: $4.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Let It Slide Nubuck Strap Sandals
Let these sandals slide into your everyday rotation! They feature an almond toe, dual nubuck straps, and a flat sole. Complete the look in a flowy blouse and skinny jeans for a coffee date.

Fit & Features
- Almond toe
- Nubuck dual straps
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1006

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lotus Floral Mesh Bodycon Dress
Look lovely in this floral mesh bodycon dress for a trendy afternoon tea look! Features a sleeveless, cowl neckline, adjustable spaghetti straps, on a mini-length hem. Complete the look in cute heels and a straw hat.

Fit & Features
- Sleeveless, cowl neckline, adjustable spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Floral mesh-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4363

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bora Bora Floral Chiffon Maxi Dress
Got vacay on the mind? This floral chiffon maxi dress is perfect for a trip to Bora Bora! Features a sleeveless, halter neck with tie-closure, ruched bust, and a cutout bodice atop a flowy, tiered maxi skirt. Complete the look in wedges and chic sunglasses.

Fit & Features
- Sleeveless, halter neck, tie-closure
- Ruched bust
- Cutout bodice
- Flowy, tiered maxi skirt
- Floral print
- Airy chiffon fabric, inner lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4391

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunset Walk Floral Midi Dress
Take a stroll at sunset on your relaxing vacay in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, an asymmetrical midi-length hem creating an alluring side slit, and a curve-hugging silhouette. The all-over tropical floral print pairs perfectly with strappy sandals. Complete the look with hoop earrings.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back design
- Asymmetrical midi-length hem, ruching, side slit
- Form-fitting silhouette
- Tropical floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4374

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Weekend Vibes Linen Midi Skirt
Bring the chic weekend vibes with this on-trend linen midi skirt. It features a flattering high-rise waist, ruched detailing down the side leading to a high slit, and a fitted, mid-length silhouette. Style with a crop top and strappy sandals.

Fit & Features
- High-rise waist
- Side zipper closure
- Side ruching, high side slit
- Fitted, mid-length silhouette
- Linen fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06301-0108

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Festival Vibes Wide-Leg Pants
Showcase trendy festival vibes all season with these fab flare pants! They feature a high-rise waist, a form-hugging fit throughout, and a wide-leg hem. Style with the matching crop top and retro shades.

Shop Matching Top: Festival Vibes Halter Crop Top

Fit & Features
- High-rise elasticized waist
- Form-hugging fit
- Wide-leg hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0801

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On Vacay Tropical Puff Sleeve Top
On vacay or just dreaming about sandy beaches? This cute tropical puff sleeve top is definitely a must! It features short puff sleeves, a square neckline, and an ultra-cropped hem with pleat detail and back zipper closure. Complete the look in the matching bottom.

Shop Matching Bottoms: On Vacay Tropical Tiered Shorts

Fit & Features
- Short puff sleeves
- Square neckline
- Ultra cropped hem
- Pleat detail, back zipper closure
- Tropical pattern
- Woven-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1572

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On Vacay Tropical Tiered Shorts
On vacay or just dreaming about sandy beaches? This cute tropical-tiered short is definitely a must! It features a high-rise waist and a tiered flowy design. Style with the matching crop top.

Shop Matching Top: On Vacay Tropical Puff Sleeve Top

Fit & Features
- High-rise waist
- Tiered flowy design
- Tropical floral pattern
- Wove-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0160

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Star Of The Show Crochet Sweater
An effortless crochet sweater for layering or styling alone! It's designed with a star front design that adds a trendy touch and a relaxed fit for comfort.

Fit & Features
- Sheer crochet fabric
- Crew neck
- Relaxed long sleeves
- Front star design
- Relaxed fit hem
- Runs true to size
Style Number/Barcode: 06005-000049

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Approved Printed Crop Top
This tropical palm leaf printed crop top is totally vacay approved! It features a sleeveless one-shoulder neckline with a single spaghetti strap and a cropped, form-hugging fit. Style with the matching maxi skirt for sunset dinner by the beach.

Shop Matching Bottoms: Vacay Approved Printed Maxi Skirt

Fit & Features
- Sleeveless one-shoulder neckline
- Single spaghetti strap
- Cropped, form-hugging fit
- Tropical palm leaf print
- Knit fabric, front lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3754

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Approved Printed Maxi Skirt
This tropical palm leaf printed maxi skirt is totally vacay approved! It features a high-rise waist, a chic thigh-high side slit, and a flowy, floor-length silhouette. Style with the matching crop top for sunset dinner by the beach.

Shop Matching Top: Vacay Approved Printed Crop Top

Fit & Features
- High-rise elasticized waist
- High side slit
- Maxi-length, flowy silhouette
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0542

Category Name: Vacation Looks

Price: $6.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend Getaway Floral Midi Dress
Pack this adorable floral printed midi dress in your carry-on for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, ruched detailing down one side leading to a slit, and a midi-length, curve-hugging fit. Style this dress with your fave oversized shades and espadrille wedges.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching down one side leading to a slit, adjustable drawstring
- Midi-length, form-fitting silhouette
- All-over floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4383

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paradise Falls Wide Leg Pants
Bring on paradise! Look so sultry in this palm print tube top featuring a strapless neckline with an o-ring center insert and an adjustable back tie closure. Complete the look in the matching bottoms.

Shop Matching Top: Paradise Falls O-Ring Tube Top

Fit & Features
- High rise waist
- Wide-leg silhouette
- Pull-on/off styling
- Palm print
- Stretchy lined fabric
- Runs true to size
Style Number/Barcode: 06502-0716

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Paradise Falls O-Ring Tube Top
Bring on paradise! Look so sultry in this palm print tube top featuring a strapless neckline with an o-ring center insert and an adjustable back tie closure. Complete the look in the matching bottoms.

Shop Matching Bottoms: Paradise Falls Wide Leg Pants

Fit & Features
- Strapless neckline
- O-ring center insert
- Adjustable back tie closure
- Palm print
- Stretchy lined fabric
- Runs true to size
Style Number/Barcode: 06001-3755

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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