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.

Taking It Easy High Rise Cut Off Shorts
Take it easy in these cut-off shorts that keep your look laidback! The shorts feature a high-rise waist, heavy destruction, and a cut-off cheeky fit hem. Complete the look with a tie-dye top and sneakers.

Fit & Features
- High rise waist
- Heavy destruction
- Cut-off cheeky fit hem
- Multi-button down closure
- Traditional five-pocket, belt loop design
- Non-stretch denim fabric
- Fits true to size
Style Number/Barcode: 06603-0162

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Beauty Mesh Mini Dress
Get a stunningly beautiful look in this floral mesh mini dress! It features spaghetti straps, a scoop neckline, ruched detailing, and a mini length, curve-hugging silhouette. The mesh fabric has an all-over foiled floral print, making it the perfect dress choice for a date night with bae. Complete your outfit with rhinestone statement earrings and strappy heels.

Fit & Features
- Spaghetti straps
- Scoop neckline
- Ruched detailing
- Short, form-hugging fit
- Mesh fabric
- Foiled floral print
Style Number/Barcode: 05101-0679

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
No Drama Destructed Denim Shorts
Leave the drama behind in these chic shorts. The shorts feature a high rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, destructed detailing, and a mid-thigh length. Complete your look with a basic crop top and sneakers for that casual feel.

Fit & Features
- High rise waist
- Single-button and zipper closure
- Traditional five-pocket and belt loop design
- Mid-thigh length
- Destructed detailing
- Form hugging fit, moderate stretch
Style Number/Barcode: 06603-0149

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beautiful Bloom Ruched Midi Dress
Showcase your beauty in this stylish floral printed midi dress! It features spaghetti straps, a square neck and back, ruched detailing, and a mid-length, curve-hugging fit. Pair this dress with strappy heels and a rhinestone necklace for a romantic date night.

Fit & Features
- Spaghetti straps
- Square neck and back
- Ruched detailing
- Mid-length
- Form-hugging silhouette
- Floral print
- Knit fabric with plenty of stretch
Style Number/Barcode: 05101-0949

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
High Rise Destructed Diva Denim Shorts
Rise up in these destructed shorts that are perfect for a casual day out. The shorts feature a high rise waist, a traditional five-pocket with belt loop design, moderate destruction, and a cuffed hem. Complete the look with a cute tank and sneakers.

Fit & Features
- High rise waist
- Traditional five-pocket with belt loop design
- Moderate destruction
- Cuffed hem
- Medium wash denim
- Form-hugging fit
Style Number/Barcode: 06603-0158

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High Rise Button-Down Denim Shorts
Elevate your denim game with shorts that bring the edge! The shorts feature a high rise waist, a multi-button down front, a traditional five-pocket with belt loop design, and heavy destruction. Complete the look with a long sleeve crop top.

Fit & Features
- High rise waist
- Multi-button down front
- Traditional five-pocket with belt loops
- Heavy destruction
- Faded medium denim fabric
- Form-hugging fit
Style Number/Barcode: 06603-0159

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Faux Suede Quilted Chevron Crossbody
Go glam with a crossbody that showcases your taste for the luxe life! The crossbody features a quilted chevron design, a fold-over closure with clasp detail, and is composed of a faux suede material. Complete look with a chic mock neck top and high waist jeans.

Fit & Features
- Quilted chevron design
- Fold-over closure with clasp detail
- Faux suede
- Detachable chain shoulder strap
Style Number/Barcode: 07203-0401

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Beauty Statement Earrings
Bring the effortless beauty like the boho babe you are in these gorgeous statement earrings. They feature an intricate design of pastel-hued gemstones leading to cascading tassel detailing. Pair these bold earrings with an off the shoulder top for a flirty look.

Fit & Features
- Pastel-hued gemstone design
- Tassel detailing
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0756

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunkissed and Snatched Halter Midi Dress
Serving body, legs, and “where’d you get that?” energy. This halter midi dress hugs every curve in a flattering bodycon fit while the cutouts do all the flirting! Pair with cute sandals or mules.

Fit & Features
- Stretchy knit fabric
- Halter neckline with tie straps
- Side cutouts
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000022

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Icy Rhinestone Baseball Cap
Flex in this glam cap that showcases your affinity for the luxe life! The cap features a traditional baseball cap design and a rhinestone embellishment that reads: "Icy". Complete look with a crop top and faux leather joggers.

Fit & Features
- Traditional baseball cap design
- Rhinestones
- Embellishment reads: "Icy"
Style Number/Barcode: 07302-0289

Category Name: Vacation Looks

Price: $6.97 $13.90

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: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Butterfly Babe Hoop Earrings
These hoop earrings will give your stylish 'fit a cute and trendy vibe. They feature an open hoop design with an intricately detailed butterfly base. Pair these adorable earrings with a casual dress and chunky sneaks.

Fit & Features
- Open hoop design
- Butterfly base
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0754

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Two Pack Rhinestone Butterfly Bobby Pins
Adorn your tresses with shimmering butterfly bobby pins that bring the dazzle. The pack includes two bobby pins that feature rhinestone embellished butterflies. Complete the look with a bodysuit and jeans for an effortlessly cute look.

Fit & Features
- Pack includes two bobby pins
- Rhinestones
- Butterfly design
Style Number/Barcode: 07006-0200

Category Name: Vacation Looks

Price: $5.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Touch of Chic Boater Hat
Add a touch of chic to your look with a trendy boater hat! The hat features a boat design with a short brim, a dainty chain-link trim, and composed of a faux wool material. Complete look with a ribbed bodysuit and black skinny jeans.

Fit & Features
- Boater design
- Short brim
- Dainty chain-link trim
- Faux wool material
Style Number/Barcode: 07302-0284

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Chic Chain Link Mask Chain
Dazzle with a mask chain to keep your face mask or sunglasses close by, girl! The chain features a trendy chain-link design and lobster clasp closures. Complete your look with a chic face mask.

Fit & Features
- Trendy chain-link design
- Lobster clasp closures
- Can be attached to use on a face mask or sunglasses
Style Number/Barcode: 07308-0149

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rhinestone Star Charm Necklace
Add a little sparkle to your chic look with this pretty necklace! It features a dainty chain with a center star charm embellished with mini rhinestones. Pair this necklace with a sleek ring pack for a trendy vibe.

Fit & Features
- Dainty chain
- Star charm
- Mini rhinestones
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0586

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rhinestone and Butterfly Charm Bracelet Five Pack
Layer up with dainty bracelets that bring the charm. This set includes five bracelets that feature a dainty rhinestone bar charm, a mini buttery charm design, and a chain-link design.

Fit & Features
- Pack includes five bracelets
- Dainty rhinestone bar charm
- Mini butterfly charm design
- Dainty chain link design
- Adjustable bolo closure
Style Number/Barcode: 07003-0215

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Rhinestone Heart Buckle Faux Leather Belt
Create a flattering silhouette while also bringing the glam in this trendy faux leather belt! It features a gold metal heart-shaped buckle with two rows of rhinestone embellishments. Pair this belt with your fave pair of mom jeans.

Fit & Features
- Faux leather belt
- Gold metal heart-shaped buckle
- Rhinestone embellishments
Style Number/Barcode: 07301-0251

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Extra Chunky Chain Link Necklace
This necklace is not for the basic babe! Showcase your affinity for all things extra life with this over the top necklace! The necklace features a chunky chain link design and a lobster clasp closure. Complete look with a bodycon dress.

Fit & Features
- Chunky chain link design
- Lobster clasp closure
Style Number/Barcode: 07002-0578

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make 'Em Look Cubic Zirconia Statement Ring
Make em look your way, and keep them here to stay! This statement ring wraps around your finger with sheer elegance! Complete your look with a formal dress and heels for a sophisticated evening outfit.

Fit & Features
- Cubic Zirconia
- Ability to stretch slightly
- Open-ended
Style Number/Barcode: 07004-0120

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Faux Wool Panama Hat
Keep it chic with a statement hat to style tresses with! The hat features a traditional Panama design with a faux leather band to adorn the brim and is composed of a faux wool material. Complete look with a moto jacket.

Fit & Features
- Traditional Panama design
- Short brim
- Faux leather band
- Faux wool
Style Number/Barcode: 07302-0281

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Layered Chain Link Anklets
Accessorize with these trendy layered chain link anklets to add a boho-chic vibe to your look! The set features two anklets, one with two rows of dainty chains, and the other with varying sized circular charms. Pair these anklets with your favorite pair of chunky sneakers.

Fit & Features
- Two-pack layered design
- Dainty chain links
- Circular charms
- Adjustable lobster clasp closures
Style Number/Barcode: 07003-0202

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Natural Beauty Butterfly Charm Necklace Pack
Showcase natural beauty with dainty necklaces that bring the charm. The pack includes three necklaces that can be worn alone or layered for a gorgeous look. The pack features a rhinestone embellished choker, a butterfly outline cham, and a rhinestone embellished butterfly charm. Complete look with a floral dress and wedges.

Fit & Features
- Pack includes three necklaces
- Butterfly charm
- Rhinestones
- Rhinestone choker
- Lobster clasp closure
Style Number/Barcode: 07002-0556

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Weekend Lace-Up Espadrille Wedges
Unlock coastal vibes in these cute lace-up espadrille wedges for a picnic or strolling the boardwalk.

Fit & Features
- Almond toe
- Lace-up ankle straps
- Wedge heel
- Espadrille material
- Runs true to size
Style Number/Barcode: 07406-000004

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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