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.

Fab And Trendy Rhinestone Low Heel Mules
These fab and trendy rhinestone mules will amp up your looks! They feature an open square-shaped toe, a wide banded strap with all-over mini rhinestone embellishments, a slide-on design with an open back, and a low block heel. Style with sleek hoop earrings.

Fit & Features
- Open square-shaped toe
- Wide banded strap, mini rhinestones
- Slide-on design, open back
- Low block heel
- Satin woven fabric, faux leather insole
- Runs true to size
Style Number/Barcode: 07404-1096

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Babe Ribbed Knit Flare Pants
Style up these comfy ribbed knit flare pants and you'll be a total trendy babe! They feature a high-rise elasticized waist, a hip-hugging fit that continues down the leg, and a flared-out hem. The ribbed knit fabric offers plenty of stretch for comfortable wear. Pair with a crop top and a button-down shacket for the cutest look!

Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flared-out hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-2262

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Downtown Girl Faux Wool Cabby Hat
You'll need this cabby hat as you make your way downtown! It features a wide brim, classic cabby-hat styling, and is made of faux wool material. Complete the look in a trendy denim jacket.

Fit & Features
- Wide brim
- Classic cabby-hat styling
- Faux wool material, woven lining
Style Number/Barcode: 07302-1395

Category Name: Vacation Looks

Price: $4.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Run This Town Platform Caged Heels
You'll run this town in elevated fashion! These chunky heels feature a square toe, caged toe straps, a platform sole, a block heel, and an adjustable ankle strap with buckle closure on faux leather material. Layer a fab faux fur jacket to complete your style slay!

Fit & Features
- Square toe
- Caged toe straps
- Platform sole
- Block heel
- Adjustable ankle strap with buckle closure
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4160

Category Name: Vacation Looks

Price: $14.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Elevated Chic Houndstooth Woven Shacket
This elevated chic houndstooth woven shacket will step up your everyday winter outfits! It features a collared neckline, long sleeves, a complete button-down front, a relaxed fit, and an all-over trendy houndstooth pattern on the woven fabric. Layer this cute shacket over a bodysuit with faux leather leggings.

Fit & Features
- Collared neckline
- Long sleeves
- Button-down front
- Chest flap pockets
- Relaxed fit
- Houndstooth pattern, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1513

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
To The Point Faux Leather Booties
These faux leather booties are essential for dressing up or down! They feature sleek pointed-toe, block-heel, and side knit panels for easy pull-on/off styling. Complete the look in a polished trench coat.

Fit & Features
- Pointed-toe
- Block heel
- Side knit panels
- Easy pull-on/off styling
- Faux leather material
Style Number/Barcode: 07403-1634

Category Name: Vacation Looks

Price: $5.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Strike Em' In Rhinestone Cowboy Hat
Strike 'em' with a glamorous look in this cowboy hat featuring a classic curved brim, and rhinestone trim, and it is composed of faux wool material—style with a casual jacket to complete the look.

Fit & Features
- Classic curved brim
- Rhinestone trim
- Cowboy design
- Faux wool material
Style Number/Barcode: 07302-1417

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Style So Sleek Faux Leather Puffer Vest
Your style will be looking so sleek layering on this faux leather puffer vest to elevate your outfit! The sleeveless vest features a standing collar neckline, front zipper and snap-button closures, hidden side pockets, and a fitted hem. The vest is composed of an insulated woven fabric designed to help keep you cozy and protected from the elements! Complete the look in casual cargo joggers.

Fit & Features
- Sleeveless, standing collar neckline
- Front zipper and snap-button closures
- Hidden side pockets
- Fitted hem
- Insulated faux leather lined fabric
- Fits true to size
Style Number/Barcode: 06201-0326

Category Name: Vacation Looks

Price: $17.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Strut It Out Abstract Zebra Tie-Front Top
Fit & Features
- Sheer mesh fabrication
- V-neckline
- Tie-front bodice
- Long sleeves
- Zebra print
- Cropped hem
- Runs true to size
Shop Matching Skirt: Strut It Out Abstract Zebra Maxi Skirt
Style Number/Barcode: 06202-0505

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Go With The Flow Floral Midi Dress
You'll love the casual vibes of this breezy floral midi dress! It features a sleeveless V-neckline with a padded bust and a draped accent, side cutouts at the waist, adjustable spaghetti straps that lead to a cross-back design, a partially open back with an elastic band, a flowy, midi-length, A-line silhouette, and a high front slit. The lightweight woven fabric features an all-over dainty floral print pattern. Style this dress with hoop earrings.

Fit & Features
- Sleeveless V-neckline, padded bust, draped accent
- Side cutouts at the waist
- Adjustable spaghetti straps, cross-back design
- Partially open back, elastic band, zipper, hook and eye closure
- Flowy, midi-length, A-line silhouette, front slit
- Floral print, woven fabric, lining at the bust, no stretch
- Runs true to size
Style Number/Barcode: 05101-2313

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
My Edgy Side One Shoulder Bodysuit
Turn up your stylish edge in this sleek and chic faux leather bodysuit featuring a one-shoulder crew neckline, a fitted long sleeve, a back keyhole with button closure, and a sultry waist cutout. Style with straight-leg jeans to complete the look!

Fit & Features
- One-shoulder crew neckline
- Fitted long sleeve
- Back keyhole with button closure
- Waist cutout accent
- Faux leather fabric
- Fits true to size
Style Number/Barcode: 06001-4383

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Best Match Plaid Slit Mini Skirt
From cool mornings to chilly afternoons, look stylish no matter the weather in this plaid mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look in the matching shacket and knee-high boots.

Shop The Matching Shacket: Best Match Plaid Longline Shacket

Fit & Features
- High-rise waist
- Back zipper closure
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Plaid pattern, soft woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06401-0462

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Best Match Plaid Longline Shacket
From cool mornings to chilly afternoons, look stylish no matter the weather in this plaid mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look in the matching cozy skirt and knee-high boots.

Shop Matching Bottoms: Best Match Plaid Slit Mini Skirt

Fit & Features
- Long sleeves, button cuffs
- Collar neckline
- Front button-down closures
- Flap pockets, side slit accents
- Longline hem
- Plaid pattern, soft woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1459

Category Name: Vacation Looks

Price: $26.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Layered In Luxe Faux Leather Trench Coat
You'll be layered in luxe in this trendy faux leather trench coat! It features a faux fur lapel collar, long sleeves with a faux fur trim, dual button-front closures, a belted waist to stylishly cinch your silhouette, and a long-line hem. The smooth faux leather fabric includes a woven lining. Pair over a crop top and a satin midi skirt with knee-high boots for a city-chic look.

Fit & Features
- Faux fur lapel collar
- Long sleeves, faux fur trim
- Dual button-front closures
- Belted waist, rectangular buckle, lined side pockets
- Long-line hem
- Faux leather fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06204-1503

Category Name: Vacation Looks

Price: $9.97 $64.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bold Glamour Gemstone Ring Set
Bring bold glamorous vibes to your everyday look with this trendy ring set! The pack features five sleek metal bands with varying designs with gemstone and rhinestone embellishments. Style this set with a dainty choker necklace.

Fit & Features
- Five-pack ring set
- Gemstone and rhinestone embellishments
Style Number/Barcode: 07004-0308

Category Name: Vacation Looks

Price: $3.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Central Park Chic Trench Coat
Layer on this structured trench coat for a city-chic look! Featuring a lapel collar, long sleeves, hidden lined side pockets, and a long-length hem, this fleece coat is a perfect pick for the season. Style over a mock neck bodysuit with dark wash denim.

Fit & Features
- Lapel collar
- Long sleeves
- Dual hidden side pockets, smooth woven lining
- Long-length hem, fitted silhouette
- Fleece fabric, little to no stretch
- Runs true to size
Style Number/Barcode: 06201-0330

Category Name: Vacation Looks

Price: $23.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wild Style Zebra Print Midi Skirt
Show off a trendy wild style in this eye-catching zebra print midi skirt! It features a high-rise waist, a midi-length hem with a sultry thigh-high side slit, and a hip-hugging fit flowing out to an A-line silhouette. The skirt is composed of a knit fabric with a moderate stretch. Style with a basic bodysuit and ankle booties.

Fit & Features
- High-rise waist
- Midi-length hem
- High side slit
- Form-hugging fit throughout the hips
- A-line silhouette
- Zebra print pattern, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0798

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Trendsetter Faux Fur Sweater
Showcase your trendsetter status with this posh sweater! It features long sleeves, a tie-front design, and a removable faux fur collar to make the look more casual. Style this sweater over a basic tank with high-rise jeans and booties.

Fit & Features
- Long fitted sleeves
- Tie-front design
- Removable faux fur collar, button details
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1026

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendsetting Girl Faux Fur Coat
Trendy and elevated, this faux fur coat will amp up your winter wardrobe! It features a collared neckline, long sleeves, a complete button-down front, lined side pockets, a mid-length hem, and a chic all-over houndstooth pattern. The ultra-soft faux fur fabric includes a smooth lining. Style with platform booties.

Fit & Features
- Collared neckline, long sleeves
- Button-down front
- Lined side pockets
- Mid-length hem
- Houndstooth pattern
- Faux fur fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0366

Category Name: Vacation Looks

Price: $9.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fur Real Slay Knit Crop Cardigan
Slay your outfit of the day with this cropped cardigan! It features fitted long sleeves, a faux fur removable collar with buttons, tie-front closure, and a slit on stretchy rib-knit fabric. Style with faux leather pants to complete the look!

Fit & Features
- Fitted long sleeves
- Faux fur removable collar with buttons
- Tie-front closure with slit
- Cropped hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1696

Category Name: Vacation Looks

Price: $8.97 $43.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
In The Knit Cable Sweater Dress
A fashionista like you needs to set the trends! Step it up this season in this staple cable knit sweater dress featuring a ribbed mock neck and long sleeves, a bodycon silhouette, and a short-length hem. Style with knee-high boots and a jacket to complete the look!

Fit & Features
- Ribbed mock neck and long sleeves
- Bodycon silhouette
- Short-length hem
- Cable knit design
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1564

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Always Luxe Faux Fur Long Coat
You'll always look luxe when you layer your 'fits with this sophisticated faux fur coat! Featuring a lapel collar, long sleeves, an open front, lined side pockets, and a long-length hem, this coat will elevate your winter wardrobe. The ultra-soft faux fur fabric includes a smooth lining. Style over a mini dress with knee-high boots.

Fit & Features
- Lapel collar
- Long sleeves
- Open front
- Lined side pockets
- Long-length hem
- Faux fur fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0321

Category Name: Vacation Looks

Price: $23.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Girly Chic Lace Trim Mini Skort
Serve all the girly chic vibes in this cute mini skort designed with a drop waist, pleating, and a peeking lace trim.

Fit & Features
- Ponte knit fabric, moderate stretch
- Drop waist design
- Pleating
- Mini-length overlay, skater silhouette, sheer lace trim
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000052

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: BLACK

Available Size: S, M, L
Chill Day Faux Wool Belted Vest
Add this faux wool vest to keep cozy and cute on chilly days! It features a sleeveless, collar neckline, open-front design, belted waist with belt loop accents, front pockets, and a long-length hem. Style with a button-down tunic top to complete the look.

Fit & Features
- Sleeveless collar neckline
- Open-front design
- Belted waist and belt loop accents
- Front pockets
- Long-length hem
- Faux wool fabric, no stretch
- Fits true to size
Style Number/Barcode: 06201-0296

Category Name: Vacation Looks

Price: $9.97 $46.90

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