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.

Faux-Ever Your Fave Shoulder Purse
This sleek little faux leather purse will quickly become your forever fave, trust us!
- Rectangular design
- Top metal clasp opening
- Lined interior
- Included metal and acrylic linked shoulder strap
- Faux leather material
Style Number/Barcode: 07203-0339

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Straight To Business One Piece Jumpsuit
Get right to it with this one-and-done jumpsuit! Layer this look with a chic blazer and heels and you got a boss-babe OOTD!

Fits & Features
- Elastic Ruffle Shoulder Straps
- Plunging V Neckline I Elastic Square Back I Back Zipper WIth Hook & Eye
- Fully Lined Woven Bodice
- Paperbag Tie Waist I Slant Hand Pockets
- Woven Fabric I Tapered Pant Legs
- Side Slits At Leg Opening
- Form Hugging I Moderate Stretch
Style Number/Barcode: 06302-0116

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Seaside Babe Button Front Midi Skirt
The perfect little getup for our resort babe! Slip into this set and look chic and comfy for your spring vacay! Make sure you add the matching top to cart before you check out

Shop Matching Top: Seaside Babe Off Shoulder Crop Top

Fits & Features
- High Rise Waist
- Button Down Front
- Midi Length Silhouette
- Textured Knit Fabric I Fully Lined
- Matching Top Sold Separate
Style Number/Barcode: 06301-0070

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Seaside Babe Off Shoulder Crop Top
The perfect little getup for our resort babe! Slip into this set and look chic and comfy for your spring vacay! Make sure you add the matching bottoms to cart before you check out

Shop Matching Bottoms: Seaside Babe Button Front Midi Skirt

Fits & Features
- Elastic Off Shoulder Neckline & Short Sleeves
- Drawstring Tie At Center Front & Down The Sleeves
- Back Zipper With Hook & Eye Closure
- Fully Lined Textured Knit Fabric
- Form Hugging Fit I Minimal Stretch
- Matching Bottoms Sold Separate
Style Number/Barcode: 06003-0900

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Do It All Strap Open Back Denim Jumpsuit
You can do it all in this chic jumpsuit! Elevate your outfit by slipping into a pair of wedges or heels!

Fits & Features
- Adjustable Spaghetti Straps
- Plunging V Neckline
- Elastic Smocked Open Back
- Lined, Hidden Hand Pockets
- Back Zipper I Wide Pant Legs
- Sturdy Denim Fabric
- Relax Fit I Moderate Stretch
Style Number/Barcode: 06602-0137

Category Name: Vacation Looks

Price: $6.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Such A Doll Ditsy Floral Tube Top
You'll look like such a doll in this adorable ditsy floral tube top! Pair with a denim skirt and some wedges for a perfect spring time vibe.

Fit & Features
- Strapless square neckline
- Cropped
- Smocked
- All over ditsy floral print
- Form hugging fit
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0715

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glow Up Button-Front Cropped Vest
Hit the scene in the glow up button-front cropped vest. This ribbed knit piece flaunts a sleeveless V-neckline and a chic button-front. Perfect for adding a touch of glam to any outfit.

Fit & Features
- Lurex knit fabric
- Sleeveless V-neckline
- Single button-front closure
- Fitted cropped ribbed hem
- Runs true to size
Style Number/Barcode: 06005-2149

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: In Stock

Available Color: GOLD

Available Size: M, L
Product Badge:
- Sale
Paper Bag Tie Waist Cargo Shorts
Tie your adorable look all together with these high waist woven cargo shorts! Paired with a chic blouse, they're perf for a dressier spring time event!

Fit & Features
- High rise elastic banded paper bag waist
- Tie front belt
- Two large front cargo style pockets
- Woven fabric with a pretty sheen | No stretch
Style Number/Barcode: 06403-0107

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Crochet Cutie Lace Triangle Bralette
We love a bralette that can be worn as a top or underneath! Pair this with a denim skirt or some cut-offs for a cute look!

Fits & Features
- Dual Adjustable Spaghetti Straps
- Cross Back
- Crochet Fabric I Lined At The Bust
- Scalloped Hemline
- Pull-Over Design
Style Number/Barcode: 07107-0398

Category Name: Vacation Looks

Price: $15.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Babe Floral Halter Romper
Pack your bags, but don't forget this romper! Style your look with a panama hat and a pair of slide-on sandals!

Fits & Features
- Tie Halter Neckline
- Keyhole Front
- Back Zipper With Hook & Eye Closure I Back Tie Waist
- Wide Leg Shorts I Pleated Design
- Chiffon Fabric I Fully Lined
- Relax Fit I Minimal Stretch
Style Number/Barcode: 06403-0103

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Crochet Queen Off The Shoulder Crop Top
Reign in the boho chic style like the true queen you are in this crochet crop top! Paired with some high rise denim and strappy sandals, your look will be effortlessly gorgeous.

Fit & Features
- Elastic banded off the shoulder neckline
- Long sheer bell sleeves
- Cropped | Ribbed hem
- Sheer crochet fabric | Knit lining
- Moderate stretch
Style Number/Barcode: 06005-0347

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Perfect Peplum Off The Shoulder Top
We love a top with a perf peplum detail! This adorable off the shoulder top is oh so flattering & amazing for spring!

Fit & Features
- Off the shoulder neckline
- Ruffle overlay | Tie front
- Long flared sleeves | Smocked details
- Stretchy smocked waist
- Ruffle peplum hem
- Eyelet crochet trim
- Lighweight woven fabric
Style Number/Barcode: 06003-0852

Category Name: Vacation Looks

Price: $11.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Crinkle Detail Square Neck Blouse
Get an effortlessly pretty look with this lightweight and airy blouse. It features long balloon sleeves with elastic cuffs, a square neck with ruffle detailing along the shoulders, and an elastic banded ruffle mid-length hem. Top is composed of a sheer crinkle detail sheer woven fabric with no stretch.

Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 06003-0507

Category Name: Vacation Looks

Price: $12.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Flow Front Slit Wide Leg Pants
Go with the flow and rock boho-chic vibes in these breezy pants! Don't forget to pick up the matching crop top to complete the look!

Shop Matching Top: Boho Flow Tie Back Crop Top

Fits & Features
- High Rise Waist I Elastic At The Back
- Flowy Wide Leg Openings
- Thigh High Front Slits
- Boho-Inspired Print I Gauze Fabric
- Relaxed Fit
Style Number/Barcode: 06302-0089

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Find Me On The Beach Studded Sandals
Find me on the beach walking in the sand with my new studded sandals! Pair with high waist denim and a graphic tee, or simple bathing suit!
- Open square toe
- Thong design
- Dainty stud detailing
- Adjustable pin buckle closure
- Faux leather
Style Number/Barcode: 07404-0562

Category Name: Vacation Looks

Price: $11.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Get Groovin' Tie Dye Scoop Neck Mini Dress
Get to movin' bb girl! This fab and fun mini dress features a splash of tie-dye print and goes perfect with white booties or sneakers!

Fits & Features
- Tank Shoulder Straps
- Scoop Neckline
- Mini Length Hemline
- Smooth Brush Knit Fabric | Tie Dye Print
- Form Hugging Fit | Plenty Of 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: 05102-0523

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Swing Into It Ruffle Mini Dress
Get into the swing of spring by refreshing that wardrobe with this cute mini dress! Slip into some block heels and add a rattan bag for a gorge look!

Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline With Snap Button Closure
- Button Closure At Back I Keyhole Opening I Back Zipper
- Ruched Drawstring At The Front
- Mini Length Silhouette I Tiered Ruffle-Trim Hem
- Woven Fabric I Full Knit Lining
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0718

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Goddess Mood Metallic Braided Sandals
Embrace your inner goddess with a pair of stunning braided sandals!
- Thong design
- Wrap around braided ankle
- Metallic finish
- Flat sole
- Zipper closure back of heel
Style Number/Barcode: 07404-0535

Category Name: Vacation Looks

Price: $11.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Studded Stunna Bow Jelly Sandals
Girllllll, Your pedi is not the only thing they're lookin' at! Slip into these cute af jelly sandals!
- Pyramid Stud Accents Along The Strap & Bow Tie
- Open Almond Toe
- Flat Sole
- Composed Of Jelly Material
Style Number/Barcode: 07404-0534

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunset Beauty Tropical Print Maxi Dress
Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.

Fit & Features
- Sheer knit fabric with mini-length knit lining, high stretch
- Tropical print
- Sleeveless cowl neckline
- Spaghetti straps, cross-back design
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-6074

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
In My Element Wide Leg Pants
Whatever the occasion, you'll be in your element once you slip into these pants! Don't forget to pick up the matching crop top for a put-together 'fit!

Shop Matching Top: In My Element Convertible Crop Top

Fits & Features
- High Rise Waist
- Pleated Details
- Wide Pant Legs I Built-In Shorts Lining
- Side Zipper With Hook & Eye Closure
- Cotton Blend Fabric I Lined At The Top
- Relax Fit I Minimal Stretch
Style Number/Barcode: 06402-0212

Category Name: Vacation Looks

Price: $13.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bold Flirt Floral Mesh Mini Skirt
Bold and flirty will be your vibe in this mini skirt featuring a large floral print to turn heads. The mid-rise waist paired with the short form-hugging fit create a sultry silhouette.

Shop Matching Top: Bold Flirt Floral Mesh Tube Top

Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Mid-rise waist
- Mini-length hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-000002

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Change It Up Crocodile Mini Envelope Fanny Pack
Dress it up in crocodile print babe! This mini fanny is the cutest little touch to your look! Style it by cinching over your biker shorts & sneaker look!
- Mini envelope fanny
- Snap closure
- Faux leather
- Croc print embossing
- Adjustable belt
Style Number/Barcode: 07203-0273

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On Another Level Nubuck Espadrille Block Heels
Girl, you're on a whole 'nother level with these heels! Pair them with that maxi dress you've been wanting to wear!
- Almond Shaped Peeptoe
- Single Band I Roller Buckle Ankle Closure
- Nubuck Fabric
- Sturdy Espadrille Block Heels
Style Number/Barcode: 07401-2176

Category Name: Vacation Looks

Price: $30.90

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