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

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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.

Stripe With It Halter Ribbed Knit Crop Top
Own this striped knit crop top all season! It's perfect for flaunting your figure with a square halter neckline and fitted crop hem. The striped pattern on the ribbed knit fabric gives it a trendy vibe. Complete the look in denim shorts for a summer fair or BBQ.

Fit & Features
- Striped pattern
- Stretchy ribbed knit fabric
- Halter square neckline, tie closure
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-1994

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Laced-Up Masterpiece Floral Slit Maxi Dress
Elevate your style with this stunning floral maxi dress that commands attention. The striking lace-up back adds an alluring touch, while the front slit reveals some skin along the form-hugging silhouette.

Fit & Features
- Floral print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Back lace-up
- Front slit
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4143

Category Name: Vacation Looks

Price: $22.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Parisian Beauty Wool Beret
Look and feel like a Parisian beauty accessorizing with this wool beret perfect for styling with a sleek crop blazer for a city-girl look.

Fit & Features
- Classic beret style
- Wool material
Style Number/Barcode: 07302-1347

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Catch Flights Tropical Lace-Up Slit Maxi Dress
Booked the trip just for the outfit? Valid. This lace-up back maxi brings the heat with a tropical print and a leg-baring high slit that knows how to make an entrance.

Fit & Features
- Smooth knit stretchy fabric, tropical print, soft knit stretch lining
- Square neckline with spaghetti straps
- Bodycon silhouette
- Lace-up open back with tie closure
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000005

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: In Stock

Available Color: ROYAL

Available Size: XS, S, M
Product Badge:
- Sale
Cozy Fall Vibes Belted Plaid Shacket
Layer on this trendy plaid flannel shacket for all the cozy fall vibes! It features a collared neckline, long sleeves, a complete button-down front, pockets, a tie-front belt to stylishly cinch your waist, and a relaxed fit. Pair with a basic bodysuit and a knit midi skirt.

Fit & Features
- Collared neckline, long sleeves, single button details
- Button-down front
- Buttoned chest pockets, faux side pockets
- Tie-front belt
- Relaxed fit
- Plaid print, woven flannel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1447

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Factor Oversized Sunglasses
Amp up the chic factor of your everyday 'fits with these sleek oversized sunglasses. They feature an oversized slightly angled design with a thin gold metal frame and nose bridge, thin gold metal arms with long cutouts, tinted lenses, and built-in nose pads for support. Pair these stylish shades with hoop earrings.

Fit & Features
- Oversized angled design
- Thin gold metal frame and nose bridge
- Thin gold metal arms with long cutouts
- Tinted lenses
- Built-in nose pads
Style Number/Barcode: 07008-1097

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: BLACK

Available Size: NS
Cute Retreat Straw Envelope Clutch Crossbody Bag
A straw clutch crossbody bag features a detachable wristlet strap, a front flap with snap-button closure, and a detachable shoulder strap for multiple styling options. Perfect for vacation retreats or summer styling.

Fit & Features
- Detachable wristlet strap
- Front flap with snap-button closure
- Detachable shoulder strap
- Straw material
Style Number/Barcode: 07203-2071

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Chic Over-The-Knee Boots
These fitted over-the-knee boots are so effortlessly chic. They feature an almond-shaped toe, a block heel, and an inner zipper closure. The boots are composed of a half faux suede and half stretchy knit composition. Style with a sweater dress and a trendy boater hat.

Fit & Features
- Over-the-knee fitted design
- Almond-shaped toe
- Block heel
- Partial inner zipper closure
- Half faux suede and half stretchy knit composition
- Runs true to size
Style Number/Barcode: 07402-0812

Category Name: Vacation Looks

Price: $12.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry For The Summer Crochet Halter Mini Dress
Create a sultry look for the summer in this sheer crochet mini dress featuring a halter V-neckline with wooden beaded accents and a short, curve-hugging silhouette to flaunt your figure.

Fit & Features
- Sheer crochet knit fabric, moderate stretch
- Sleeveless V-neckline, wooden beaded accents
- Tie-back halter straps, wooden beaded accents
- Partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000063

Category Name: Vacation Looks

Price: $32.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Feelin' Sweet Chiffon Halter Babydoll Dress
You'll be feelin' sweet and chic in this airy chiffon mini dress featuring a halter cutout neckline and flowy babydoll silhouette. Perfect for pairing with pearl earrings.

Fit & Features
- Sheer chiffon fabric with woven lining, no stretch
- Sleeveless halter neckline, V-cut bust
- Adjustable spaghetti straps, partially open back
- Flowy babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4035

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Always In Plaid Woven Crop Shacket
Don't be surprised if you find yourself wearing this plaid crop shacket on repeat! It features long sleeves with button cuffs, a collar neckline, a button-down placket, pockets, and a boyfriend silhouette. Complete the look in knee-high boots for a chic autumn outfit!

Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button-down placket, pockets
- Boyfriend silhouette
- Cropped hem
- Plaid pattern, flannel woven fabric
- Fits true to size
Style Number/Barcode: 06204-1454

Category Name: Vacation Looks

Price: $21.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Vacay Attitude V-Neck Floral Tropical Maxi Dress
Book those tickets and pack a bag cause vacation is calling and this floral tropical maxi dress is ready to answer! Made from an airy floral tropical printed chiffon fabric with a short woven lining, this dress is perfect for summer days. Featuring spaghetti strap tassel ties and V-neckline, cutout sides add a touch of flirty fun, while the flowy maxi-length silhouette and front slit provide style. Complete the look with a straw tote bag and sandals!

Fit & Features
- Tropical floral print, chiffon fabric, short woven lining
- Spaghetti strap tassel ties
- V-neckline
- Cutout sides
- Front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3446

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Total Doll Halter Crop Top
Step out looking like a fashion icon in this halter crop top, perfect for a haute night out! Pair with the matching skirt to complete the look.

Fit & Features
- Stretchy knit fabric
- Halter V-neckline, keyhole accent
- Fitted crop hem
- Runs true to size
Shop The Matching Skirt: Total Doll Ruffle Mini Skirt
Style Number/Barcode: 06001-000097

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: In Stock

Available Color: PINK

Available Size: M, L
Product Badge:
- Sale
Keep It On Check Plaid Crop Jacket
Keep your fall look in check in this plaid crop jacket perf for the cozy season! It features long sleeves, a collar neckline, snap-button front closures, flap pockets, and a pull tab hem with button closure. Complete the look in trendy boots.

Fit & Features
- Long sleeves, collar neckline
- Snap-button front closures
- Flap pockets
- Pull tab hem with button closure
- Cropped length
- Plaid pattern, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1421

Category Name: Vacation Looks

Price: $18.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Enticing Flirty Sleeveless Lace-Up Denim Romper
Entice them all with your flirtiness in this denim romper perfect for festivals, concerts, or casual plans! Featuring a square neckline and adjustable thin tank straps, this romper hugs your curves and offers a flirty lace-up front. Perfect for a casual day out, and with a short-length hem, it's the ultimate summer must-have. Complete the look in trendy cowboy boots.

Fit & Features
- Dark wash cotton-blend denim fabric, moderate stretch
- Square neckline
- Adjustable tank straps
- Back zipper with hook and eye closure
- Lace-up
- Form-hugging
- Runs true to size
Style Number/Barcode: 06603-0380

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Iconic Getaway Tie-Waist Wrap Fringe Skirt
Get ready for an iconic getaway with this tie-waist wrap fringe skirt perfect for days spent under the sun or sipping on drinks poolside!

Fit & Features
- Crochet knit design, sewn-in knit lining
- Wrap-tie waist
- Back zipper and hook-eye closure
- Cascading fringe hem
- Runs true to size
Style Number/Barcode: 06501-000032

Category Name: Vacation Looks

Price: $42.90

Availability: In Stock

Available Color: IVORY

Available Size: S, M, L
Love For Fall Plaid Cropped Shacket
Showcase your love for this cozy season with this on-trend cropped shacket. It features a collared neckline, long sleeves, a multi-button down front, and a cropped, cinched back hem. The flannel woven fabric features an all-over plaid print, perfect for the fall time. Layer over a bodysuit with faux leather pants for an elevated look.

Fit & Features
- Collared neckline
- Long sleeves, button details
- Multi-button down front
- Buttoned chest pockets
- Cropped hem with a cinched back
- Plaid print, flannel woven fabric
- Runs true to size
Style Number/Barcode: 06204-1450

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Weekend Chic Linen Tie-Front Corset Romper
Show up looking casual-chic for your weekend plans in this adorable tie-front corset romper! Designed with a lightweight linen woven fabric, it features a sleeveless square neckline with adjustable spaghetti straps offering a customized fit leading to a back zipper closure. The corset bodice will create that cinched silhouette, followed by a tie-front belt for a cute touch. Style with espadrille wedges.

Fit & Features
- Linen woven fabric
- Square neckline
- Adjustable spaghetti straps, back zipper and hook-eye closure
- Corset bodice, flexible boning
- Tie-front belt, side pockets
- Runs true to size
Style Number/Barcode: 06303-0251

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vibe Of Summer Tie Front Eyelet Crop Top
This gorgeous eyelet crop top will bring you the vibe of summer vacations and parties! The sweetheart neckline flatters your look while the tie front design and spaghetti straps add a playful touch to the cropped hem on breezy eyelet fabric. Complete the look with the matching maxi skirt.

Shop Matching Bottoms: Vibe Of Summer High Rise Eyelet Maxi Skirt

Fit & Features
- Eyelet fabric, moderate stretch
- Spaghetti straps
- Sweetheart neckline
- Tie front
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5358

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Major Sweetie Gingham Lace-Up Peplum Crop Top
Have yourself the sweetest summer in this gingham peplum top! Featuring playful puff sleeves and a flattering lace-up peplum ruffle, this crop top is perfect for any occasion.

Fit & Features
- Gingham print, cotton woven fabric
- Puff short sleeves
- Sweetheart neckline
- Spaghetti strap tie back design, stretchy smocked panel
- Front lace-up
- Peplum ruffle crop hem
- Runs true to size
Style Number/Barcode: 06003-000029

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: BLK/WHT

Available Size: S, M, L
Festival Vibes Halter Crop Top
Showcase trendy festival vibes all season with this alluring crop top! It features a sleeveless halter neckline with spaghetti straps in a cross-front design and a cropped, form-hugging fit. Style with the matching wide-leg pants and retro shades.

Shop Matching Bottoms: Festival Vibes Wide-Leg Pants

Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, cross-front design, tie at the back of the neck
- Cropped, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06001-4029

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blooming Beauty Floral Print Mesh Maxi Dress
Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels!

Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Floral print
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Bodycon-like fit
- Long maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3785

Category Name: Vacation Looks

Price: $44.90

Availability: Out of Stock
Product Badge:
- Ships Free
Minimalistic Chic Faux Leather Belt
Add the perfect touch of chic to your look with this faux leather belt featuring a sleek metal buckle accent, dual bands with perforated holes, and a pull-through design. Complete the look in a form-fitting jumpsuit and heels.

Fit & Features
- Sleek metal buckle accent
- Dual faux leather bands
- Perforated holes
- Pull-through design
Style Number/Barcode: 07301-0468

Category Name: Vacation Looks

Price: $3.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Meet Me in the Meadow Chiffon Floral Maxi Dress
Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.

Fit & Features
- Floral print, chiffon fabric, short woven lining
- Strapless smocked bodice
- Flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000107

Category Name: Vacation Looks

Price: $52.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L

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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