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.

The Good Life Geometric Sunglasses
Live the good life with chic sunglasses to pack on your next vacay, babe! The sunglasses feature an oversized geometric-shaped frame, nose pads, and sleek arms. Complete look with a romper and sandals.

Fit & Features
- Oversized geometric frames
- Nose pads
- Sleek arms
Style Number/Barcode: 07008-0891

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Chic Espadrille Platform Sandals
Keep it casually chic with stylish sandals that are perf for keeping it lowkey! The sandals feature an open back, wide criss-cross ankle straps, an open almond toe with strap over the toe, and an espadrille platform. Complete look with a high-low floral dress and gold huggies.

Fit & Features
- Open back
- Wide criss-cross ankle straps
- Open almond toe, strap over the toe
- Espadrille platform
- Faux leather
- Runs true to size
Style Number/Barcode: 07404-0923

Category Name: Vacation Looks

Price: $12.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On Trend Rimless Ombre Sunglasses
Keep your look on-trend with a chic pair of sunglasses for your next beach day! The sunglasses feature rectangular-shaped frames, nose pads, ombre-hued lenses, and sleek arms. Complete look with a romper and sandals.

Fit & Features
- Rectangular-shaped frames
- Nose pads
- Ombre-hued lenses
- Sleek metal arms
- 100% UV protection
Style Number/Barcode: 07008-0902

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Iconic Diva Round Rainbow Sunglasses
Dazzle like the iconic diva you are with sunglasses that are everything! The sunglasses feature a round frame, a rainbow-hued trim, light-hued lenses, and sleek arms. Complete look with a matching crop top and skirt set!

Fit & Features
- Round frame
- Rainbow-hued trim
- Light-hued lenses
- Sleek arms
- 100% UV protection
Style Number/Barcode: 07008-0905

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fierce And Fab Leopard Print Sandals
Keep your summertime look fierce and fab with these trendy sandals. They feature an open round toe, a toe strap and adjustable ankle strap with a leopard print design, and a flat sole. Style these sandals with a casual dress.

Fit & Features
- Open round toe
- Toe strap, adjustable ankle strap, circular buckle detail
- Leopard print
- Runs true to size
Style Number/Barcode: 07404-0941

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wild At Heart Sunglasses
Hey babe, showcase your wild and trendy style with these cool shades! The sunglasses feature a heart-shaped design, a plastic frame with an all-over leopard print, and tinted lenses. Wear these shades with a basic tee and denim shorts.

Fit & Features
- Heart-shaped design
- Plastic frame, leopard print
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0906

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All Eyes On Me Floral Eyelet Maxi Dress
Draw all eyes on you in this bold maxi dress! The dress features a vibrant floral print, an eyelet pattern, a sleeveless V-neckline, spaghetti straps, dual waist cutouts, and a maxi-length silhouette with a flared hem. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Includes a mini skirt-length knit lining. Complete look with sandals and hoops.

Fit & Features
- Floral print
- Sleeveless V-neckline, spaghetti straps
- Dual waist cutouts
- Eyelets
- Maxi length silhouette
- Lightweight woven fabric, mini skirt knit lining
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4123

Category Name: Vacation Looks

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortless Chic Mid-Rise Ruffled Shorts
Effortless for vacay or weekend fun, these chic shorts are designed with a smocked drawstring high-rise waist and a ruffled hem!

Fit & Features
- Cotton woven fabric
- Flowy short sleeves
- V-neckline
- Tie-front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06303-000008

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK, LIGHT, BLUE, RED, OFF, WHITE

Available Size: S, M, L, XS
Product Badge:
- Sale
Vacay Beauty Floral Maxi Skirt
You'll look like a stylish beauty as you jet off to your next vacay in this maxi skirt! It features a high-rise waist, side ruched detailing leading to a thigh-high slit, a fitted silhouette, and a fab all-over tropical floral print. Complete the look with the matching crop top and some chic shades.

Shop Matching Top: Vacay Beauty Floral Crop Top

Fit & Features
- High-rise waist
- Side ruched detailing
- Thigh-high slit
- Fitted silhouette
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 06501-0404

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Beauty Floral Crop Top
You'll look like a stylish beauty as you jet off to your next vacay in this crop top! It features a sleeveless V-neckline with a center bar strap design, spaghetti straps, a cropped, form-hugging fit, and a fab all-over tropical floral print. Complete the look with the matching maxi skirt and some chic shades.

Shop Matching Bottoms: Vacay Beauty Floral Maxi Skirt

Fit & Features
- Sleeveless V-neckline
- Center bar strap design
- Spaghetti straps
- Cropped, form-hugging fit
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 06001-3269

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Studded Strappy Sandals
These cute strappy sandals have a chic studded design that is so on-trend! They feature an open round toe, a toe strap, an adjustable ankle strap, a flat sole, and a stylish studded trim. Wear these sandals with your fave casual dresses.

Fit & Features
- Open round toe
- Toe strap
- Adjustable ankle strap, buckle detail
- Flat sole
- Studded trim
- Runs true to size
Style Number/Barcode: 07404-0845

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beach Bound Straw Tote
You'll be totally ready for your next beach trip with this adorable straw tote. It features a woven design with dual wooden O-ring handles. Style this bag with sandals and cute shades.

Fit & Features
- Straw material, woven design
- Dual wooden O-ring handles
- Nylon woven lining
Style Number/Barcode: 07203-0771

Category Name: Vacation Looks

Price: $12.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wrapped In Style Faux Suede Sandals
Wrap yourself in stylish sandals this season for that next weekend getaway! The sandals feature wrap-around straps, an open almond toe with toe loop strap, and a flat footbed. The sandals are composed of a faux suede material. Complete look with a romper and hoops.

Fit & Features
- Wrap around straps
- Open almond toe
- Toe loop strap
- Faux suede material
- Runs true to size
Style Number/Barcode: 07404-0942

Category Name: Vacation Looks

Price: $7.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual And Trendy Strappy Sandals
These casual and trendy sandals are perf for the summer season. They feature an open square-shaped toe, a multi-colored strappy design with leopard print and croc-embossed details, and a flat sole. Style these sandals with a basic tee and denim shorts.

Fit & Features
- Open square-shaped toe
- Multi-colored strappy design
- Leopard print and croc-embossed details
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0940

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Simply Stylish Strappy Sandals
Simple and stylish, these faux leather sandals are the perfect pair for summer. They feature an open round toe, a thin strappy design, and a flat sole. Wear these sandals with denim shorts.

Fit & Features
- Open round toe
- Thin strappy design
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0939

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Chic Jelly Strappy Sandals
Keep it casual with cute jelly sandals that go with everything! The sandals feature an adjustable ankle strap, an open square toe with a strap over the toe, and composed of a jelly material. Complete look with a romper and studs.

Fit & Features
- Adjustable ankle strap
- Open square toe
- Strap over the toe
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-0926

Category Name: Vacation Looks

Price: $7.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feelin' Boho Scallop Hem Knit Hot Shorts
Create a boho babe vibe in these high-rise knit hot shorts with a cheeky form-hugging fit and trendy scalloped hem. Style with the matching top for festival season!

Shop Matching Top: Feelin' Boho Halter Open Back Knit Top

Fit & Features
- Sweater knit fabric
- High-rise banded waist
- Cheeky form-hugging fit
- Scalloped hem
- Runs true to size
Style Number/Barcode: 06503-1275

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Paisley Chic High Waist Shorts
Keep it chic in paisley shorts that will have you ready for festival season! The shorts feature a high-rise waist, a paisley print, and a cheeky fit. Complete look with the matching crop top.

Shop Matching Crop Top: Paisley Chic Tie Front Crop Top

Fit & Features
- High rise waist
- Paisley print
- Cheeky fit
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0254

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Forever Fierce Snake Print Mini Dress
Keep your look forever fierce in this trendy snake print mini dress. It features a sleeveless square neckline, bungee spaghetti straps, and a short, form-fitting silhouette to hug your curves. Style this dress with clear heels for a night out with the girls.

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Mini-length, form-hugging fit
- Snake print
- Knit fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05103-3928

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Sunsets Asymmetrical Midi Dress
Take in those tropical vibes with a midi dress that will have you vacay-ready! The dress features a tropical palm leaf print, a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and an asymmetrical hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops and sandals.

Fit & Features
- Tropical palm leaf print
- Sleeveless scoop neckline
- Adjustable spaghetti straps, cross at back
- Midi length silhouette
- Asymmetrical hem
- Smooth knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4111

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fabulous Floral Puff Sleeve Mini Dress
Keep your look fresh and fab in this adorable floral printed mini dress! It features a sweetheart neckline with a tie at the bust, short puff sleeves, and a short, curve-hugging silhouette. Style this dress with strappy sandals and chic sunnies.

Fit & Features
- Sweetheart neckline, tie at the bust
- Short puff sleeves, elastic cinched hems
- Mini-length, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-4125

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreamy Floral Asymmetrical Midi Dress
Get a gorgeous and dreamy look in this chic floral midi dress. It features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back design, ruched detailing, and a mid-length, curve-hugging silhouette with a high-cut asymmetrical hem. Style this dress with cute wedges.

Fit & Features
- Sleeveless scoop neckline, spaghetti straps
- Open back, cross-back design
- Ruching
- Mid-length, form-hugging fit
- High-cut asymmetrical hem
- Knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-1113

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Serving Prep & Sass Bubble Mini Skirt
This skirt said “main character energy” and meant it. With a playful bubble mini hem and classic pinstripe print, she’s made for casual hangs, day dates, and being the moment.

Fit & Features
- Pinstriped print, cotton woven fabric, sewn-in woven lining
- High-rise waist
- Side zipper and hook-eye closure
- Flouncy bubble mini hem
- Runs true to size
Style Number/Barcode: 06301-000005

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: In Stock

Available Color: LIGHT, BLUE

Available Size: M, L
Product Badge:
- Sale
Casual-Chic Vibes Crochet Crop Top
Showcase casual-chic vibes in this crop top that is perf for summer. It features a sleeveless V-neckline, spaghetti straps, and a cropped fit with a cute scalloped hem. The crochet fabric makes this top a must-have for weekend getaways. Style it with high-rise flare pants and sandals.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Cropped fit, scalloped hem
- Crochet fabric
- Runs true to size
Style Number/Barcode: 06005-0974

Category Name: Vacation Looks

Price: $4.97 $24.90

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