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.

Perfect Knit Distress Crop Sweater
The perfect knit crop sweater to level up your autumn closet! The crew neck sweater features long sleeves and a hem with distressed accents on a purl knit fabric. Complete your trendy look in high-rise jeans and booties for everyday styling!

Fit & Features
- Long sleeves and hem with distressed accents
- Crew neck
- Cropped length
- Purl knit design
- Fits true to size
Style Number/Barcode: 06005-1548

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Femme Edge Platform Lug Booties
Play up your edgy female energy in these faux leather booties featuring a trendy utility design, a round toe, block heel, chunky platform lug sole, knit side panels, and inner zipper closure on an ankle-length shaft. Complete the look in a cool moto jacket!

Fit & Features
- Round toe
- Block heel
- Chunky platform lug sole
- Side knit panels and inner zipper closure
- Ankle-length shaft
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1559

Category Name: Vacation Looks

Price: $12.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cold Babe Plaid Blanket Scarf
You can still be a babe and brace for the cold thanks to this cozy plaid blanket scarf! It features a trendy fringe edge design on cozy and soft fabric. Complete the look in a trendy jacket for a coffee run.

Fit & Features
- Plaid pattern
- Fringe edge design
- Soft and cozy fabric
Style Number/Barcode: 07305-0431

Category Name: Vacation Looks

Price: $3.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Best Of Friends Color Block Sweater
You and this cozy sweater will be the best of friends! The sweater top features color block long sleeves, a crew neck, a ribbed-knit design, and a relaxed fit hem. Complete the look in skinny jeans.

Fit & Features
- Color block long sleeves
- Crew neck
- Relaxed silhouette
- Ribbed-knit design
- Comfortable and soft fabric
- Fits true to size
Style Number/Barcode: 06005-1521

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The OG Rock Babe Slash Graphic Tee
Flaunt your original status as a rock babe in this edgy graphic tee featuring short sleeves, a crew neck with a V-cut notch, a slashed hem, and a front script that reads, "The Original Rock N Roll". Complete the look in sleek faux leather shorts for a concert!

Fit & Features
- Short sleeves
- Crew neck
- V-cut notch
- Slashed crop hem
- Front script that reads, "The Original Rock N Roll"
- Graphic detailing
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1428

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Jay High-Rise Wide Leg Jeans By Windsor Denim
Easy, breezy, and effortlessly cool slip into the Jay jeans by Windsor denim designed to showcase your edgy-cute style! They feature a flattering high-rise waist, front distressed accents, and knee rips along the wide-leg silhouette. The jeans are crafted from a medium wash with vintage-inspired color fading for the perfect worn-in fit and feel. Complete the look in sleek pointed-toe booties.

Fit & Features
- High-rise waist
- Front distressed accents, knee rips
- Wide-leg silhouette
- Hidden front five-button fly
- Five-pocket styling, belt loop accents
- Medium wash denim, color fade effect
- Runs true to size
Style Number/Barcode: 06602-0380

Category Name: Vacation Looks

Price: $6.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Look Back At Me Cable Knit Top
Watch head-turn as you walk by in this fab cable knit sweater top featuring a sleeveless mock neck, a flirty open-back design, and a cropped hem. Pair with skinny jeans and booties for a fall festival!

Fit & Features
- Sleeveless mock neck
- Open-back design
- Cropped hem
- Cable knit sweater fabric
- Soft and comfortable
- Fits true to size
Style Number/Barcode: 06005-1673

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sultry Bloom Floral Mesh Tube Top
Serve a sultry vibe in this blooming floral printed mesh tube top! Designed with ruched side seams to show off your curves, style with the matching maxi skirt for a gorgeous look.

Shop Matching Bottoms: Sultry Bloom Floral Mesh Maxi Skirt

Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Strapless straight neckline, no-slip strip
- Ruched side seams
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-5714

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreamy Date Vibes Satin Cropped Blouse
Get a dreamy-chic look for date night with this sleek satin cropped blouse! It features a deep V-neckline with a wrap-front, long peasant sleeves with smocked hems, a lace-up back design, and a cropped, form-hugging fit. The lightweight woven satin fabric has no stretch. Style with faux leather pants and heels.

Fit & Features
- V-neckline, wrap-front
- Long peasant sleeves, tapered smocked hems
- Lace-up back design, tie closure
- Cropped hem, form-hugging fit
- Woven satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1831

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Press Pause Faux Leather Corset Bodysuit
You'll wanna press pause cause you'll be obsessed with how you slay in this faux leather corset bodysuit perfect for a night out. It features a sleeveless sweetheart neckline, adjustable and detachable spaghetti straps, ruched bust, fitted bodice, and mesh thong bottom with dual snap-button closures. Complete the look in straight-leg jeans.

Fit & Features
- Sleeveless sweetheart neck
- Adjustable and detachable spaghetti straps
- Ruched bust, back zipper closure
- Corset-style fitted bodice
- Mesh thong bottom, dual snap-button closure
- Faux leather non-stretch lined fabric
- Runs true to size
Style Number/Barcode: 06003-1972

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Rock Babe Lace-Up Graphic Dress
If you're a rock babe this graphic short dress is the one for you! It features short sleeves, a crew neck, a front lace-up placket, and graphic detail with a script that reads, "Rock N Roll World Tour" along the fitted hem. Complete the look in over-the-knee boots.

Fit & Features
- Short sleeves
- Crew neck
- Front lace-up placket
- Graphic detail/ front reads, "Rock N Roll World Tour"
- Short and fitted hem
- Jersey knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1459

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Casual Cropped Denim Trucker Jacket
Layer on the casual vibes with this vintage-inspired cropped denim trucker jacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, side pockets, and a cropped fit. Style over a basic tee with distressed jeans.

Fit & Features
- Collared neckline
- Drop shoulder design, long sleeves, single button detailing
- Button-down front
- Buttoned chest pockets, side pockets
- Cropped
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0473

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Winter Strolls Fringe Scarf
This ultra-soft lightweight scarf is perfect for staying cozy on outdoor strolls this winter season. It features an oblong design with fringe detailing at the hems. The faux wool material has no stretch. Style with lace-up boots.

Fit & Features
- Oblong design
- Fringe detailing
- Soft faux wool material, no stretch
Style Number/Barcode: 07305-0425

Category Name: Vacation Looks

Price: $4.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wrap Me In Plaid Fringe Scarf
Layer on this plaid scarf to brace for the cold weather ahead! It features a fringe edge design on super soft and cozy fabric. Complete the look in a cute shacket and jeans.

Fit & Features
- Plaid pattern
- Fringe edge design
- Soft and cozy fabric
Style Number/Barcode: 07305-0432

Category Name: Vacation Looks

Price: $1.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Strut In Style Over-The-Knee Boots
Strut in style in these sleek faux leather over-the-knee boots. They feature an almond-shaped toe, a tall block heel, an inner zipper closure, and a tie-back detail at the top. Pair with a bodycon dress and a moto jacket.

Fit & Features
- Over-the-knee design
- Almond-shaped toe
- Block heel
- Partial inner zipper closure
- Tie-back detail
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0811

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Safari Babe Zebra Cowl Midi Dress
Go on safari looking like a total babe in this zebra midi dress sure to make you in charge of the animal kingdom! It features a sleeveless cowl neckline, dual spaghetti straps, and a form-hugging silhouette. Complete the look in strappy mules for brunch!

Fit & Features
- Sleeveless cowl neckline
- Dual spaghetti straps
- Form-hugging silhouette
- Midi-length hem
- Zebra print
- Knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-2026

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Knit Girl Cold Shoulder Sweater
If you're a girl who loves her knit sweaters this one is for you! The cold shoulder sweater features cozy long sleeves with ribbed cuffs, a turtle neckline, a relaxed fit, and a cropped hem ribbed knit fabric. Complete the look in a skirt and knee-high boots.

Fit & Features
- Long sleeves, ribbed cuffs
- Turtle neckline
- Cold shoulder accents
- Relaxed fit
- Cropped hem
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06005-1588

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
She's A Trendsetter Zebra Faux Fur Coat
Layer on this fab zebra-printed faux fur coat for a total trendsetter vibe. It features an open front with a lapel collar, long sleeves, front pockets, and a relaxed fit. The zebra-printed faux fur fabric is ultra-soft to the touch for cozy wear. Style over a sweater dress with ankle booties.

Fit & Features
- Open front, lapel collar
- Long sleeves
- Lined front pockets
- Relaxed fit
- Zebra print
- Faux fur fabric, smooth lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0335

Category Name: Vacation Looks

Price: $14.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cable Knit Vibes Crop Sweater
Embrace the autumn chill in this cable knit crop sweater featuring cozy long sleeves and a crew neckline on soft acrylic-knit fabric. Complete the look in jeans and knee-high boots.

Fit & Features
- Cozy long sleeves
- Crew neckline
- Cable knit design
- Cropped hem
- Soft acrylic-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1523

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Trend Alert Cropped Puffer Vest
Keep your status as a stylish trendsetter with this fab cropped puffer vest! It features a sleeveless collared neckline, a complete zip front, a cropped hem, and adjustable drawcords on each side for a cinched fit. The vest is composed of a lined nylon-woven fabric with insulation to help keep you warm and protected from the elements. Layer over a long sleeve top with your fave pair of denim.

Fit & Features
- Sleeveless collared neckline
- Zip front
- Cropped hem
- Adjustable drawcords
- Insulated and lined nylon-woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0336

Category Name: Vacation Looks

Price: $18.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make Hearts Flutter Butterfly Hair Clip
Make his heart flutter in this whimsical butterfly hair claw clip! Perfect for sweeping your hair up into a chic updo. Complete the look in a casual dress for a day date.

Fit & Features
- Butterfly hair claw clip
- Sleek metal frame
Style Number/Barcode: 07006-0351

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cutie At Heart Cutout Mini Skirt
Sweeten your every vibe in this bodycon mini skirt with a heart insert and a cutout that adds a cute look!

Fit & Features
- Smooth knit stretchy fabric
- High-rise waist
- Heart insert and cutout
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06501-000006

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: S, M, L
Product Badge:
- Sale
Peek-A-Boo Faux Suede Booties
Peek-a-boo do you see these chic shoes? Strut the catwalk in these faux suede booties featuring a peep toe almond toe, block heel, and a front lace-up placket and side zipper closure. Complete the look in a wide-leg jumpsuit.

Fit & Features
- Peep almond toe
- Block heel
- Front lace-up placket
- Side zipper closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07403-1483

Category Name: Vacation Looks

Price: $38.90

Availability: Out of Stock
Product Badge:
- Sale
Close Up Square Toe Block Heels
You'll be ready for your close-up in these faux leather block heels featuring a trendy square toe, platform sole, and an adjustable buckle ankle strap. Complete your gorgeous look in a chic ring set.

Fit & Features
- Square toe
- Platform sole
- Block heel
- Adjustable buckle ankle strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3973

Category Name: Vacation Looks

Price: $4.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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