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.

Cozy Diva Faux Fur Collar Jacket
Even divas want to be cozy and cute on their off-duty days! Keep it chic in this faux fur jacket featuring long sleeves, a collared neckline, an open-front design, hidden side pockets, and a mid-length hem. Style with best-selling shoes to complete the look!

Fit & Features
- Long sleeves
- Collared neckline
- Open-front design
- Hidden side pockets
- Mid-length hem
- Faux fur fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0374

Category Name: Vacation Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Delicate Beauty Six-Pack Earrings Set
Dainty and delicate, adorn your ears with these beautiful earrings! The six-pack set features pairs of two in assorted styles perfect for everyday or formal styling. Complete the look in glitzy block heels for a celebration!

Fit & Features
- Six-pack earring set with lobster clasp closures
- One metal studs
- One rhinestone studs
- One faux pearl studs
- One geo-shaped studs
- One chain-twist hoop studs
- One dangly chain studs
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1449

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Whimsical Statement Flower Earrings
Add these charming and whimsical statement earrings to your look! They feature a large flower design with rhinestone embellishments and a post-back closure. Style with a chic ring set.

Fit & Features
- Flower design
- Rhinestone embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1454

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Nautical Charm Flower Huggies
The perfect blend of nautical and charm! These huggie earrings feature rhinestone flower charms on a sleek metal half-hoop with an omega closure. Complete the look in a cute denim jacket for a day date.

Fit & Features
- Rhinestone flower charm
- Sleek half-hoop
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1453

Category Name: Vacation Looks

Price: $2.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bringing The Heat Abstract Cutout Mini Dress
You'll bring the sizzle to every party in this sexy abstract mini dress! The halter neckline with hoop insert adds a trendy touch while the cutout front and bodycon fit make a statement.

Fit & Features
- Abstract print, mesh fabric, stretchy knit lining
- Halter neckline with tie straps, hoop insert
- Front cutout
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000307

Category Name: Vacation Looks

Price: $38.90

Availability: In Stock

Available Color: ORANGE

Available Size: M, L
It-Girl Layered Chain Necklace Set
Give off that it-girl energy when you accessorize your 'fits with this trendy necklace set. It features a flat chain-link choker necklace and a longer paperclip chain-link necklace detailed with a faux pearl accent and a toggle closure. Style this set with rhinestone stud earrings.

Fit & Features
- Two necklaces
- Flat chain-link choker necklace, adjustable chain, lobster clasp closure
- Longer paperclip chain-link necklace, faux pearl accent, toggle closure
Style Number/Barcode: 07002-1360

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cool-Girl Layered Charm Necklace Set
Step up your 'fits and achieve that cool-girl style with this trendy layered necklace set! It features a flat chain-link choker necklace and a double-layered dainty chain-link necklace with a rhinestone flower charm and a cascading lariat with rhinestone accents and a mini rhinestone star charm. Pair this necklace set with stud earrings.

Fit & Features
- Two necklaces
- Flat chain-link choker necklace
- Double-layered chain-link necklace
- Rhinestone flower charm
- Lariat, rhinestone accents, rhinestone star charm
- Adjustable chains, lobster clasp closures
Style Number/Barcode: 07002-1366

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Swirls Of Style Satin Midi Dress
Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.

Fit & Features
- Sleeveless v-neck, adjustable spaghetti straps
- Flexible boning inserts
- Back zipper and hook-eye closure
- Front slit, curve-hugging, midi-length hem
- Marble print
- Satin fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4867

Category Name: Vacation Looks

Price: $5.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
A Little Sassy Platform Block Heels
A little sassy yet completely eye-catching! Rock these faux suede heels with your going-out fit. They feature an open square toe, wide toe strap, a chunky platform sole, triangular block heel, and a closed ankle with lace-up straps. Complete the look with a crop denim jacket.

Fit & Features
- Open square toe, wide toe strap
- Chunky platform sole
- Triangular block heel
- Closed ankle
- Lace-up straps
- Faux suede material
- Runs true to size
Style Number/Barcode: 07401-4177

Category Name: Vacation Looks

Price: $34.90

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Shine Rhinestone Stud And Duster Earrings Set
Show off a chic shine with this effortlessly chic earrings set! The multipack features nine pairs of dainty studs and linear duster earrings in varying rhinestone designs that will give both your casual and dressy looks the prettiest sparkle. Style these earrings with a rhinestone ring set for all the more glamour.

Fit & Features
- Nine pairs of studs and linear duster earrings
- Various rhinestone embellished designs
- Post-back closures, rubber stoppers
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1521

Category Name: Vacation Looks

Price: $2.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
City Girl Plaid Faux Wool Coat
Layer on this plaid faux wool coat for a chic city girl look! It features a lapel collar, an open front, long sleeves, lined side pockets, and a mid-length hem with a fitted silhouette. The all-over plaid print will give your 'fit that classic vibe. Style over a sweater dress with knee-high boots.

Fit & Features
- Lapel collar, open front
- Long sleeves
- Side pockets, smooth lining
- Mid-length hem, fitted silhouette, back slit accent
- Plaid print
- Faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0315

Category Name: Vacation Looks

Price: $27.97 $62.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
A Polished Vibe Plaid Faux Wool Coat
Layer on this plaid faux wool coat for a polished vibe! Featuring a lapel collar, an open front, long sleeves, side pockets, a mid-length hem, and a fitted silhouette, this coat is a definite winter staple. The all-over plaid print will keep your looks classic and chic. Style with faux leather ankle booties.

Fit & Features
- Lapel collar, open front
- Long sleeves
- Side pockets, back slit accent
- Mid-length hem, fitted silhouette
- Plaid print
- Unlined faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0313

Category Name: Vacation Looks

Price: $27.97 $62.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
All The Feels Faux Fur Lined Denim Jacket
Cuddle up in this trendy denim jacket to layer over all of your favorite crop tops and bodysuits! It features a faux fur hood, long sleeves, a multi-button down front, pockets, and a relaxed fit. The denim fabric features an ultra-soft faux fur lining for a warm and cozy feel. Style this jacket with distressed jeans and combat boots.

Fit & Features
- Faux fur hood
- Long sleeves, faux fur cuffs
- Multi-button down front
- Dual buttoned chest pockets, faux side pockets
- Relaxed fit
- Denim fabric, faux fur lining
- Runs true to size
Style Number/Barcode: 06203-0480

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Coffee First Cable Knit Bodysuit
Got coffee on your mind? Look cute for your run to the shop in this cable knit bodysuit featuring long sleeves, a ribbed mock neck, a form-hugging fit, and a thong bottom with dual snap-button closure. Style with high-rise jeans for the perf look!

Fit & Features
- Long sleeves
- Ribbed mock neck
- Form-hugging
- Thong bottom, dual snap-button closures
- Cable knit design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1535

Category Name: Vacation Looks

Price: $11.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Fabulous Vibe Faux Fur Crop Jacket
Layer on this luxe faux fur crop jacket for to give off a fabulous vibe! It features a lapel collar, an open front, long sleeves, and a fitted, cropped hem. The ultra-soft faux fur fabric features an all-over illusion stripe design to give the look of a trendy puffer design. Style with a faux leather mini skirt and heels.

Fit & Features
- Lapel collar
- Open front
- Long sleeves
- Fitted, cropped hem
- Soft faux fur fabric, smooth woven lining, no stretch
- Illusion stripe design
- Runs true to size
Style Number/Barcode: 06201-0368

Category Name: Vacation Looks

Price: $26.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Stylishly Edgy Faux Leather Flare Pants
Show off a cool-girl vibe in these stylishly edgy faux leather flare pants! They feature a high-rise waist with a five-pocket and belt loop design, a front button and zipper closure, a hip-hugging fit, and a flared-out hem. The smooth-coated faux leather fabric offers a moderate stretch. Pair with a corset top and clear heels.

Fit & Features
- High-rise waist
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Hip-hugging fit
- Flared-out hem
- Coated faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06402-0670

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
That's My Type Mock Neck Zip Top
This everyday basic is just your type! The long sleeve top features a mock neck, front zipper closure, and a fitted hem on rib-knit fabric. Complete the look in a mini skirt and a jacket.

Fit & Features
- Long sleeves
- Mock neck
- Front zipper closure
- Fitted hem
- Rib-knit fabric
- Fits true to size
Style Number/Barcode: 06002-1498

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Taylor High-Rise Destructed Skinny Ankle Jeans by Windsor Denim
This pair of Taylor skinny ankle jeans by Windsor Denim will instantly become a new fave! They feature a high-rise waist, light-destructed detailing down the front, a skinny-leg fit, and an ankle-cut hem. The dark wash denim fabric features minimal stretch and color fading for the perfect vintage look. Style with a crop top and booties.

Fit & Features
- High-rise waist
- Light-destructed detailing down the front
- Skinny-leg fit, ankle-cut hem
- Five-pocket and belt loop design
- Front button and hidden zipper closure
- Dark wash denim fabric, minimal stretch, color fading
- Runs true to size
Style Number/Barcode: 06602-0379

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Appearance Side-Tie Wrap Denim Skort
Your summer style wouldn't be the same without this mini denim skort to make stylish appearances! This form-hugging, high-waisted denim skort boasts a stylish faux wrap skirt overlay with a side tie, adding both function and flair to your wardrobe. The frayed hem adds a touch of edginess. Complete the look in a basic top.

Fit & Features
- Dark wash denim, slight stretch
- High-rise waist, front zipper closure
- Faux wrap skirt overlay, side-tie
- Form-hugging fit
- Frayed short hem
- Runs true to size
Style Number/Barcode: 06603-0390

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Delicate Blooms Flower Hair Clips
Tame your tresses while giving your hair a luxe look! This hair clip set features a flower design with rhinestone embellished petals, a faux pearl center, and a sleek metal frame. Style with sleek hoop earrings to complete the look!

Fit & Features
- Hair clip set
- Flower design
- Rhinestone embellished petals
- Faux pearl center
- Sleek metal frame
Style Number/Barcode: 07006-0377

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Factor Snake Chain Panama Hat
Amp up the chic factor of your look with this trendy panama hat! It features a structured top with a wide flat brim and a sleek snake chain trim. Style with hoop earrings.

Fit & Features
- Panama hat design
- Structured top
- Wide flat brim
- Thin snake chain trim
- Faux wool material
Style Number/Barcode: 07302-1393

Category Name: Vacation Looks

Price: $4.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
See My Style Clear Box Handbag
Show everyone your new favorite handbag! It features a clear box-shape design, a rhinestone handle, push-lock closure, and a detachable chain link strap. Complete the look in rhinestone heels for a social occasion!

Fit & Features
- Clear box-shape design
- Top push-lock closure
- Rhinestone handle
- Spacious interior
- Detachable chain link strap
Style Number/Barcode: 07204-0678

Category Name: Vacation Looks

Price: $14.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dazed And Chic Hoop Earrings Set
Everyone will be in a daze at you in these chic hoop earrings! The set features three pairs of assorted shapes and sizes with a multi-layered design, sleek twist, and textured metal frames and each with omega-back closures. Style with a posh cardigan to complete your trendy look!

Fit & Features
- Three pair earrings set
- Assorted shapes and sizes
- Sleek twist and textured metal frames
- Multi-layered design
- Each with omega-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1423

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dainty Deets Duster Earrings
You'll absolutely adore the dainty details of these duster earrings! They feature a linear design with a thin chain and small round accents. Style with a trendy ring set.

Fit & Features
- Linear design
- Thin chain
- Small round accents
- Post-back closure
- Metal material
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1434

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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