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.

Sultry And Stunning Halter Midi Dress
Get a sultry and stunning look for date night in this curve-hugging midi dress. It features a sleeveless halter neckline, an open back with a subtle strappy design, and a mid-length, form-fitting silhouette. The dress is composed of a slinky lurex fabric. Complete the outfit with a faux leather jacket and clear heels.

Fit & Features
- Sleeveless halter neckline
- Open back, strappy design
- Mid-length, form-hugging fit
- Slinky lurex fabric
- Runs true to size
Style Number/Barcode: 05101-0996

Category Name: Vacation Looks

Price: $9.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ring Me Up Strapless Romper
Built-in beach club energy. This strapless romper brings the heat with a keyhole O-ring detail and a cinched waist that flatters every curve—perfect for hot days, hotter nights, and bottomless brunches.

Fit & Features
- Woven fabric, stretchy knit shorts lining
- Sweetheart strapless neckline, hoop insert, cutout
- Back zipper and hook-eye closure
- Fitted cinch bodice
- Runs true to size
Style Number/Barcode: 06303-000027

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay On My Mind Tropical Print Shorts
You'll be ready for a vacay in these cute shorts that bring those island vibes! The shorts feature a high-rise waist, a tie waist belt with loops, a tropical palm leaf print, and a cheeky fit. Complete look with the matching crop top and kimono.

Shop Matching Crop Top: Vacay On My Mind Tropical Print Crop Top

Shop Matching Kimono: Vacay On My Mind Tropical Print Kimono

Fit & Features
- High rise waist
- Tie waist belt with belt loops
- Tropical palm leaf print
- Cheeky fit
- Chiffon fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0147

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Like Summer Crochet Maxi Skirt
Sweet like summer, this crochet maxi skirt was made to flirt. With a high-rise waist, scalloped trim, and high-cut side slit, it's your new go-to for coastal vibes. Style with the matching bralette top.

Shop Matching Top: Sweet Like Summer Crochet Bralette Top

Fit & Features
- Sheer crochet knit fabric, moderate stretch
- High-rise waist, scalloped trim
- Adjustable tie-front drawstring
- Thigh-high side slit
- Maxi-length fitted silhouette, scalloped hem
- Runs true to size
Style Number/Barcode: 06501-000096

Category Name: Vacation Looks

Price: $46.90

Availability: In Stock

Available Color: IVORY

Available Size: S, M, L
Product Badge:
- Part of a Set
Vacay On My Mind Tropical Print Crop Top
You'll be ready for a vacay in this cute crop top that brings those island vibes! The top features a sleeveless square neckline, adjustable spaghetti straps, a tropical palm leaf print, and a cropped hem Complete look with the matching shorts and kimono.

Shop Matching Shorts: Vacay On My Mind Tropical Print Shorts

Shop Matching Kimono: Vacay On My Mind Tropical Print Kimono

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- Cropped hem
- Chiffon fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1183

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty And Chic Paisley Printed Mini Dress
Showcase a pretty and chic vibe in this on-trend paisley printed mini dress. It features a sleeveless V-neckline, a tie accent at the bust, ruffle detailed shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with wedges for weekend brunch with the girls.

Fit & Features
- Sleeveless V-neckline
- Tie-front at the bust
- Ruffled shoulder straps
- Smocked back
- Short, form-hugging fit
- Paisley printed chiffon fabric
- Runs true to size
Style Number/Barcode: 05102-0571

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feelin' Fab Tie-Dye Mini Dress
You'll be feelin' oh-so-fab in this trendy tie-dye mini dress. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. This dress would be perf for a casual date styled with a cute crossbody purse and clear heels.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Ruched detailing, drawstrings at the hem
- Short, form-hugging fit
- Ribbed knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1334

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ditsy Floral Daze Ribbed Knit Mini Dress
Get caught in a floral daze with this cute mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, ruching down the sides
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-3119

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On Trend Tie Front Crop Top
Stay on trend with a crop top that is Insta-worthy! The top features a plunging sweetheart neckline with a lace-up front, short puff sleeves, and a cropped hem. The top is composed of a linen fabric that offers a form-hugging fit with minimal stretch. Complete look with cutoff shorts.

Fit & Features
- Plunging sweetheart neckline
- Lace-up front
- Short puff sleeves
- Cropped hem
- Linen fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1284

Category Name: Vacation Looks

Price: $11.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreamy Vacay Vibes Maxi Dress
Bring the dreamy vacay vibes to your next getaway in this gorgeous maxi dress. It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist, and a flowy floor-length silhouette with a chic front slit. The mesh fabric has a tropical floral print, making the maxi dress a perf pick for summer. Complete the look with strappy sandals.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back zipper closure
- High waist
- Flowy floor-length silhouette, front slit
- Mesh fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0523

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Bound Off The Shoulder Smocked Jumpsuit
You'll be looking vacay bound in this stylish jumpsuit! The jumpsuit features an off-the-shoulder neckline, with cold shoulder straps, a smocked bodice, and a relaxed fit leg with a wide-leg hem. Complete look with wedges.

Fit & Features
- Off the shoulder neckline
- Smocked bodice
- Relaxed fit straight leg
- Gauze knit fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0198

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Moment For Mesh Ruched Midi Skirt
Create a head-turning moment in a mesh skirt that commands attention! The skirt features a high-rise waist, a ruched body, and a midi length silhouette. The skirt is composed of lined mesh fabric that offers a form-hugging fit with a moderate stretch.

Shop Matching Crop Top: Moment For Mesh Ruched Crop Top

Fit & Features
- High rise waist
- Ruched body
- Midi length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0461

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Moment For Mesh Ruched Crop Top
Create a head-turning moment in a mesh crop top that commands attention! The top features a sweetheart neckline with a ruched drawstring, long sheer sleeves, and a cropped hem. Complete look with the matching midi skirt and mules.

Shop Matching Midi Skirt: Moment For Mesh Ruched Midi Skirt

Fit & Features
- Sweetheart neckline
- Ruched drawstring at the center
- Long sheer sleeves
- Cropped hem
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3576

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wanderlust Beauty Lace-Up Top
You're a total wanderlust beauty, and this crop top is a must-have style for you! The crop features a sleeveless square neckline, lace-up front, a bohemian-inspired print. The top is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching flared pants.

Shop Matching Pants: Wanderlust Beauty Flared Pants

Fit & Features
- Sleeveless square neckline
- Lace-up front
- Bohemian-inspired print
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3329

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Making Waves Tie Dye Ruched Mini Dress
Make waves with a stylish mini dress that creates a commotion! The dress features a sleeveless V-neckline, a ruched center drawstring, a tie-dye print, spaghetti straps, and a mini-length silhouette. Complete look with clear mules.

Fit & Features
- Sleeveless V-neckline
- Ruched center drawstring
- Tie-dye print
- Spaghetti straps
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4056

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual Moment Striped Tie Front Top
Create a casual moment with a tie-front top that is perf for wearing alone or layering over a cute bralette! The top features a plunging V-neckline with a tie-front accent, kimono sleeves, a striped pattern, and a cropped hem. Complete look with cutoff shorts.

Fit & Features
- V-neckline
- Kimono sleeves
- Tie-front
- Striped pattern
- Cropped hem
- Gauze knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-0827

Category Name: Vacation Looks

Price: $8.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
One Short Day Linen High-Rise Ruffle Mini Skirt
Easy and effortless, this linen mini skirt boasts a playful vibe with a ruffled hem perfect for sunny-day dressing!

Fit & Features
- Linen-blend woven fabric, sewn-in knit lining
- High-rise waist
- Side zipper and hook-eye closure
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06301-000003

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Rhinestone Glam Oversized Round Sunglasses
Bring the glam with sunglasses that give off that luxe vibe! The sunglasses feature an oversized round frame, metal nose bar with nose pads, rhinestone trim, and sleek metal arms. Complete look with a romper and wedges.

Fit & Features
- Oversized round frame
- Nose bar with nose pads
- Rhinestone trim
- Metal arms
Style Number/Barcode: 07008-0839

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Floral Lace-Up Crop Top
Keep it flirty and pretty with a crop top that channels a romantic vibe! The crop features an off-the-shoulder neckline, short puff sleeves, a lace-up front, a floral print, a smocked bodice, and a cropped hem. Complete look with high waist jeans.

Fit & Features
- Off the shoulder neckline, sweetheart bust
- Lace-up front
- Short puff sleeves
- Floral print
- Smocked bodice
- Cropped hem
- Form hugging fit runs true to size
Style Number/Barcode: 06003-0970

Category Name: Vacation Looks

Price: $4.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Metallic Moment Thong Sandals
Have a chic metallic moment in these must-have summer sandals. They feature an open round toe, a metallic thong strap design, and a flat sole. Style these sandals with your fave pair of denim shorts.

Fit & Features
- Open round toe
- Metallic thong strap design
- Flat sole
- PU material
- Runs true to size
Style Number/Barcode: 07404-0852

Category Name: Vacation Looks

Price: $7.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Extra Oversized Square Sunglasses
Rock a look that's so extra with sunglasses that bring the drama! The sunglasses feature an oversized square frame, flat top, metal accents at each corner, and sleek arms. Complete look with a romper.

Fit & Features
- Flat top
- Oversized square frames
- Metal accents
- Dark lenses
Style Number/Barcode: 07008-0836

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Let Style Bloom Ditsy Floral Tube Dress
Let your style bloom with a tube dress that is perf for those beach days! The dress features a strapless square neckline, a ditsy floral print, and a mini-length silhouette. Complete the look with mules and a crossbody.

Fit & Features
- Strapless square neckline
- Ditsy floral print
- Mini-length silhouette
- Lightweight ribbed knit fabric, knit lining
- Form-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-2876

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Twirl And Pose Crepe Skater Dress
Get ready to strike a pose with a skater dress that will have you looking on trend! The dress features a sleeveless V-neckline, spaghetti straps, a strappy back design, and a skater-length silhouette. The dress is composed of a lined crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Strappy back
- Skater length silhouette
- Lined crepe fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0778

Category Name: Vacation Looks

Price: $19.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Charmer Ditsy Floral Mini Dress
You'll charm them all in this adorable ditsy floral mini dress! It features a sleeveless sweetheart neckline with a ruffle trim, a tie-front detail, adjustable spaghetti straps, and a mini-length, curve-hugging silhouette. Style this dress with a pair of strappy sandals.

Fit & Features
- Sleeveless sweetheart neckline, ruffle trim
- Tie-front detail
- Adjustable spaghetti straps
- Partial smocked back
- Short, form-hugging fit
- Chiffon fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-0757

Category Name: Vacation Looks

Price: $9.97 $33.90

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