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 Frayed Denim Mini Skirt
Look oh so fab in this frayed denim mini skirt! With its high rise waist and form-hugging fit, it provides the ultimate flattering fit. A must-have to wear to brunch with the girls! Pair with a graphic tee and some chic shades to pull the look together.

Fit & Features
- High rise waist
- Front button closure
- Traditional five pocket and belt loop design
- Back slit
- Short frayed hem
- Form hugging fit
- Denim fabric
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06601-0031

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Frayed Hem Denim Mini Skirt
Style up this frayed hem denim mini skirt for a fun day out with your girls! Featuring a high waist and trendy frayed hem, this skirt is oh so cute. Pair with a crop top and some clear heels for the perfect look.

Fit & Features
- High rise waist
- Button front closure
- Traditional five pocket and belt loop design
- Short frayed hem
- Form hugging fit
- Denim fabric
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06601-0034

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Button Up Raw Hem Denim Mini Skirt
Button up into this adorable denim mini skirt to make your 'fit all the more trendy! With its high waist and raw cut hem, the skirt is a must-have for grabbing lunch with your squad. Pair with some wedges and tortoiseshell shades for that laid back, yet chic look.

Fit & Features
- High rise waist
- Traditional five pocket and belt loop design
- Button front closure
- Short raw cut hem
- Denim fabric
- Form hugging fit
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06601-0032

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Everyday Must Have Cuffed Jean Shorts
Yes girl, these cuffed jean shorts are an everyday must have for sure! They feature a high waist with slightly distressed detailing. Perfect for wearing to go lounge poolside! Pair with a flowy blouse and some cute wedges.

Fit & Features
- High rise waist
- Front button closure
- Traditional five pocket and belt loop design
- Swirl design detail on back pockets
- Slight destructed detailing
- Cuffed hem
- Denim fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0142

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Of The Moment Faux Leather Espadrille Sandals
Get a trendy, of the moment look in these faux leather espadrille sandals! They feature a wide faux leather band and a sporty ridged espadrille sole. Wear with a flirty floral dress and gold jewelry for your next backyard bbq!

Fit & Features
- Open round toe | Wide toe strap
- Adjustable around the ankle strap
- Open back
- Espadrille sole | Sporty ridged detail
Style Number/Barcode: 07404-0546

Category Name: Vacation Looks

Price: $13.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Dream Tie Front Crop Top
Effortlessly dreamy, this tie front crop top will pull together your boho inspired look! Featuring kimono style sleeves and a plunging V neckline, this top is perfect for a date night in. Pair with some distressed mom jeans and strappy heels to really level up your 'fit.

Fit & Features
- Three quarter length kimono style sleeves
- Deep V neckline
- Tie front
- Cropped
- Sheer woven fabric | Dot pattern
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-0551

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweeter In Stripes Strapless Romper
Keep it sweet and simple in this adorable strapless romper! It features a fun ruffled popover detail and tie front waist to make you look snatched! Perfect for a picnic in your backyard, pair it with some cute wedges and sleek gold hoops.

Fit & Features
- Strapless square neckline
- Ruffle popover detail
- High rise tie front waist
- Form-fitting shorts
- All over striped print
- Woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06303-0096

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Vacay Queen Tropical Floral Mesh Tie-Front Top
Slay your next vacay in this gorg tropical floral mesh tie-front top with long sleeves and an ultra-cropped hem. Style with the matching maxi skirt for a sultry vibe!

Shop Matching Bottoms: Vacay Queen Tropical Floral Mesh Maxi Skirt

Fit & Features
- Sheer mesh fabric, high stretch
- Large tropical floral print
- V-neckline
- Tie-front design
- Long bishop sleeves
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06202-000019

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
She's A Stunner Mesh Tie Front Top
You'll be quite the stunner in this mesh tie front top! With its sheer mesh fabric and cropped, form-fitting style, you can easily rock this over your bikini at the pool! Pair with some chic bottoms and oversized shades.

Fit & Features
- Long sleeves with elastic cuffs
- Deep V neckline
- Tie front detail
- Cropped
- Unlined sheer mesh fabric
- Moderate stretch
Style Number/Barcode: 06202-0096

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortless Eyelet Puff Sleeve Crop Top
Create an effortless everyday look in this eyelet crop top that is a must have for your summer vibe. Perfect paired with the matching mini skirt for a chic photoshoot in your backyard! The adorable top features short eyelet puff sleeves with a flirty trim and a flattering front tie. Complete your cute outfit with some classic gold hoops and trendy wedges.

Shop Matching Skirt: Effortless Eyelet Mini Skirt

Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Delicate trim
- Cropped tie front
- All over eyelet detail
- Form-fitting style
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-2625

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fierce and Fab Triangle Bralette
Keep it fierce and fab in a bralette that brings major style to your loungewear! The bralette feature triangle-shaped cups, a trendy print, and adjustable straps that provide a comfortable customized fit. Complete your look with the matching shorts and throw hair up in a cute messy bun with a scrunchie.

Shop Matching Bralette: Fierce and Fab Tulip Hem PJ Shorts

Fit & Features
- Triangle-shaped cups
- Adjustable spaghetti straps
- Elastic back
- Relaxed fit
- Matching shorts sold separately
- Available in Leopard or Floral print
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 07107-0476

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fierce and Fab Tulip Hem Pajama Shorts
Keep it fierce and fab in pajama shorts that bring major style to your loungewear! The pajama shorts feature a high rise waist, a trendy print, and a cute tulip hem. Complete your look with the matching bralette and throw hair up in a cute messy bun with a scrunchie.

Shop Matching Bralette: Fierce and Fab Triangle Bralette

Fit & Features
- High rise waist
- Tulip hem
- Cheeky bottom
- Relaxed fit
- Matching bralette sold separately
- Available in Leopard or Floral print
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 07103-0351

Category Name: Vacation Looks

Price: $9.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sassy Strap Stunner Cork Wedges
Keep it sassy in cute wedges to channel those summer vibes girl! The wedges feature an open back, an adjustable ankle strap with mini square buckle, an open almond toe with clear PVC strap over the toe, and a cork wedge heel. Complete look with a floral sundress.

Fit & Features
- Open back
- Adjustable ankle strap with mini square buckle
- Open almond toe with clear PVC strap over the toe
- Cork wedge heel
Style Number/Barcode: 07406-0231

Category Name: Vacation Looks

Price: $16.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Four Row Dainty Chain Necklace
Keep it simply chic in a necklace that keeps it sleek! The necklace features a four-row layered design and features a sleek chain-link design. Complete your look with a fab matching set.

Fit & Features
- Four-row tiered design
- Chain link
Style Number/Barcode: 07002-0402

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Essential High Waist Pajama Leggings
Add these staple pajama leggings to your cozy collection, perfect for lounging in while keeping it stylish. These leggings feature a high rise waist, a drawstring, and a skinny leg fit. Complete your laidback look with the matching PJ tank and throw up hair in a cute messy bun with a scrunchie.

Shop Matching Tank: Essential Cropped Pajama Tank

Fit & Features
- High rise waist
- Drawstring
- Skinny leg fit
- Matching tank sold separately
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 07103-0356

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Essential Cropped Pajama Tank
Add this staple pajama tank to your cozy collection, perfect for lounging in while keeping it stylish. The tank features a sleeveless square neckline, a square neckline, and a cropped hem. Complete your laidback look with the matching pajama leggings and throw up hair in a cute messy bun with a scrunchie.

Shop Matching Leggings: Essential High Waist Pajama Leggings

Fit & Features:
- Sleeveless square neckline
- Spaghetti straps
- Cropped hem
- Soft knit fabric
- Relaxed knit fabric
- Matching leggings sold separately
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 07103-0355

Category Name: Vacation Looks

Price: $9.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
X Marks the Spot Open Back Bodysuit
Stop your search, this bodysuit is the one you need in your life! The bodysuit features a scoop neckline, spaghetti straps, and a bold open back with a cross-strap accent. Complete your look with high waist denim and hoops.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back with cross-strap accent
- Snap button closure
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2650

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rhinestone Butterfly and Bar Charm Layered Necklace
Charm in a rhinestone necklace that will give major butterflies. The layered necklace features a tiered design, a dainty chain with rhinestone embellished butterfly, and bar charm. Complete look with fab matching separates and sneakers for a laidback vibe.

Fit & Features
- Tiered layered design
- Dainty chain
- Rhinestone embellished butterfly
- Rhinestone embellished bar charm
Style Number/Barcode: 07002-0444

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Button Down Beauty Maxi Dress
Button-down in a casual maxi dress for a cute day-out outfit the next time you're picking up a must-have iced coffee! This maxi dress features a plunging sweetheart neckline with a tie-front accent, mini cutout at the bodice, and a button-down front with a high center slit. Complete your look with sleek sandals for those low-key vibes.

Fit & Features
- Plunging sweetheart neckline
- Tie-front accent with a small cutout at the bodice
- Adjustable spaghetti straps
- Multi-button down front
- High center slit
- Maxi length silhouette
- Ribbed knit fabric, form-hugging fit
Navy Dress: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

Mustard Dress: Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0746

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Kara High Rise Cuffed Destructed Shorts
Oasis by Eunina

With more sun coming our way, It's essential to have a pair of high-rise shorts in your wardrobe! We love to see you pairing this with your favorite top!

Fits & Features
- High Rise Fit
- Traditional 5-Pocket Styling
- Belt Loop Design
- Button Waist I Zip Fly
- Destructed Detailing
- Frayed, Rolled Cuffs
- Denim Fabric I Moderate Stretch
Style Number/Barcode: 06603-0035

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleeveless Striped Smocked Peplum Top
Keep it sassy in a striped peplum top. The top features a sleeveless bodice, a square neckline, tie-up straps, a smocked bodice, a striped pattern, and a peplum hem. The top is composed of a smocked knit fabric that offers a relaxed fit with a moderate stretch. Complete your outfit with high waist shorts and statement earrings.

Fit & Features
- Sleeveless bodice
- Square neckline
- Tie-up spaghetti straps
- Stripped pattern
- Smocked knit fabric
- Peplum hem
- Relaxed fit, moderate stretch
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0922

Category Name: Vacation Looks

Price: $4.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Off To Paradise Tie-Front Crop Top
A trending abstract crop top designed with flowy short sleeves and a tie-front design that flaunts your figure on vacay! Pair with the matching pants.

Fit & Features
- Abstract print, stretchy knit fabric
- Short sleeves
- V-neckline
- Tie-front design
- Cropped hem
- Runs true to size
Shop The Matching Pants: Off To Paradise Wide-Leg Abstract Pants
Style Number/Barcode: 06202-000002

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: S, M
Product Badge:
- Sale
Sassy Smocked Mini Skirt
Ooo girl, you'll be lookin' sassy in this smocked mini skirt! Pair with the matching crop top for the perf look for a sunny day out!

Shop Matching Top: Sassy Smocked Crop Top

Fit & Features
- High rise elastic banded waist
- Short, form hugging fit
- Merrow edge hem
- Stretchy smocked knit fabric
- Knit lining
Style Number/Barcode: 06501-0224

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Crushing On You Long Puff Sleeve Crop Top
We're totally crushing on this crop top, perfect for that upcoming BBQ with the squad. The crop top features plunging v-neckline, long puff sleeves, tie front ties, and a cropped hem. Complete your casually cute look with high waist jeans and sunnies.

Fit & Features
- Plunging v-neckline
- Tie-front ties at center of the bodice
- Long puff sleeves
- Cropped hem
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-0943

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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