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.

Summertime Fine Cork Wedges
You’ll be looking extra fine this summer in these wedges! They feature an open almond toe, a single toe strap, an adjustable ankle strap and a cork wedge. Pair them with a sundress and oversized sunglasses.

Fit & Features
- Open almond toe
- Faux leather
- Adjustable ankle strap
- Cork Wedge
- Runs true to size
Style Number/Barcode: 07406-0263

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On Point Faux Leather Sandals
Your casual outfit will be on point when you pair it with these chic sandals! The sandals feature a single toe strap with a cross puff design, an open square toe and a flat footbed. Pair them with a bodysuit and distressed jeans.

Fit & Features
- Open square toe
- Faux leather
- Puff toe strap
- Runs true to size
Style Number/Barcode: 07404-0716

Category Name: Vacation Looks

Price: $10.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Studded Babe Faux Leather Sandals
Be a total babe this summer in these studded sandals! They feature an open round toe, a caged design with studs and an adjustable ankle strap. Pair them with a cropped graphic tee and denim shorts.

Fit & Features
- Open round toe
- Caged design
- Metal stud detailing
- Flat sole
- PU material
- Runs true to size
Style Number/Barcode: 07404-0894

Category Name: Vacation Looks

Price: $7.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Vibes Sleeveless Maxi Dress
Bring on the effortless vibes this season with this pretty maxi dress! It features a sleeveless square neckline, spaghetti straps, side pockets, and a flowy silhouette with an asymmetrical hem. Cinch the dress with a belt and style it with mules for an adorable look.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side pockets
- Flowy, relaxed fit
- Asymmetrical hem
- Smooth knit fabric
- Runs true to size
Style Number/Barcode: 05102-4171

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Major Jetsetter Tropical Print Maxi Dress
Nail your vacay-bound look with a maxi dress that brings those tropical vibes! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a high side slit, and a tropical palm leaf print. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and sunglasses.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back
- High side slit
- Tropical palm leaf print
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0542

Category Name: Vacation Looks

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho-Chic Crochet Midi Dress
Bring the boho-chic vibes to your stylish summer look with this stunning midi dress! It features a sleeveless scoop neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a sheer crochet fabric with a trendy fringe hem. Wear this dress as a cover-up over your fave bikini for the perf poolside outfit.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mid-length, form-hugging fit
- Sheer crochet fabric, fringe hem
- Runs true to size
Style Number/Barcode: 06005-0949

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty In Lace Crochet Duster
Keep it pretty in lace with a duster that is perf to layer over your gorge outfits! The duster features a draped open front, kimono sleeves, and a crochet lace pattern. Complete look with a crop top and high waist shorts.

Fit & Features
- Open front
- 3/4 kimono sleeves
- Crochet lace
- Flowy long length
- Mesh fabric
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-0907

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All That Eyelet Tie Front Top
This top is all that and more with pretty details! The top features a plunging V-neckline, long puff sleeves, tie-front, and an eyelet pattern. Complete look with a mini skirt and wedges.

Fit & Features
- V-neckline
- Long puff sleeves
- Tie-front
- Cropped hem
- Eyelet pattern
- Lightweight woven fabric
- Form hugging fit runs true to size
Style Number/Barcode: 06204-0894

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bold Muse Floral Print Tube Top
Serve fab vibes on vacay in this cropped tube top featuring a bold floral print pattern. Style with the matching maxi skirt for an iconic 'fit.

Shop Matching Bottoms: Bold Muse Floral Print Maxi Skirt

Fit & Features
- Smooth knit fabric, high stretch
- Large floral print
- Strapless straight-across neckline
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-000139

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Everyday Essential Espadrille Sandals
These trendy espadrille sandals are an everyday essential for the summer season. They feature an open round toe, a double strap design with buckle detailing, and an elevated espadrille sole. Style these sandals with a cool graphic tee and denim shorts.

Fit & Features
- Open round toe
- Double strap design, buckle detailing
- Elevated espadrille sole
- Faux leather straps
- Runs true to size
Style Number/Barcode: 07404-0854

Category Name: Vacation Looks

Price: $7.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sheer Appeal Ruched Asymmetrical Skirt
Keep it sheer and stylish with a mesh skirt makes for the perfect swim coverup! The skirt features a high-rise waist, a ruched side seam with drawstring, and an asymmetrical hem. The skirt is composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with a floppy hat!

Fit & Features
- High rise waist
- Ruched side seam with drawstring
- Asymmetrical hem
- Mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0379

Category Name: Vacation Looks

Price: $5.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Beauty Sheer Tie-Front Top
Hey beauty, showcase your chic style in this cool tie-front top! It features long bell sleeves, a V-neckline, a tie-front detail, and a cropped fit. The sheer mesh fabric has an all-over leaf pattern, making it a perf option to pack for your next vacay. Complete the look with a denim mini skirt.

Fit & Features
- Long bell sleeves
- V-neckline
- Tie-front
- Cropped
- Sheer mesh fabric, leaf pattern
- Runs true to size
Style Number/Barcode: 06204-0942

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Come Away With Me Cotton Crop Top
Come away with me, to another place, where we can sip on mimosas and take pics in our cute cotton sets! The crop top features a sleeveless square neckline, tank-like shoulder straps, and a tassel fringe. Complete the look with the matching skort.

Shop Matching Bottoms: Come Away With Me Cotton Skort

Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Tassel fringe
- Cropped hem
- Cotton fabric
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-2147

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropics Bound High Slit Maxi Skirt
Head out for the tropics with a maxi skirt that channels those vacay vibes. The skirt features a high-rise waist, a tropical palm leaf print, a high side slit, and a maxi length silhouette. Complete look with a crochet crop top and a floppy hat.

Fit & Features
- High rise waist
- Tropical palm leaf print
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0447

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
High-Rise Belted Twill Shorts
Level up your look with high waist shorts that keep your look so chic! The shorts feature a paper bag waist, an adjustable belt with a D-ring buckle, front pockets, and a cheeky fit. Complete the look with a blouse and wedges.

Fit & Features
- Paper bag waist, elastic banded back
- Adjustable belt, D-ring buckle
- Front pockets, faux back pocket
- Cheeky fit
- Twill woven fabric, no stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06303-0117

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Headturner Platform Heels
Create a major head-turning moment with these pretty platforms! The heels feature an open back, an adjustable ankle strap, an open almond toe with a strap over the toe, a raffia platform, and a block heel. Complete look with a white dress.

Fit & Features
- Open back
- Adjustable ankle strap
- Open almond toe
- Strap over the toe
- Raffia platform
- Block heel
- Denim material
Style Number/Barcode: 07401-3074

Category Name: Vacation Looks

Price: $7.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreaming Of Paradise Mesh Duster
This stunning duster will have you dreaming of a relaxing day in paradise! It features long fitted sleeves, an open front, a chic tie-front belt, and a floor-length flowy silhouette. The sheer mesh fabric has a gorgeous tropical palm leaf print to bring those vacay vibes. Style this duster over your fave bikini and top off the look with a cute floppy hat.

Fit & Features
- Long fitted sleeves
- Open front
- Tie-front belt
- Floor-length flowy fit
- Sheer mesh fabric
- Tropical palm leaf print
- Runs true to size
Style Number/Barcode: 06202-0162

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fab And Fierce Leopard Print Kimono
Keep it fierce with a kimono that can be layered over your favorite outfits! The kimono features a leopard print, a draped open front, kimono sleeves, dual side slits, and a flowy long length. Complete look with a crop top and high waist shorts.

Fit & Features
- Leopard print
- Open front
- Kimono sleeves
- Dual side slits
- Long length
- Sheer
- Relaxed fit, moderate stretch, runs true to size
Style Number/Barcode: 06204-0941

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Here For The Drama Sunglasses
You're all about that over-the-top dramatic look, so these shades are perfect for you! The sunglasses feature an oversized square-shaped design, a plastic frame with sleek metal accents on the sides, and tinted lenses. Style these sunglasses with a trendy shoulder bag.

Fit & Features
- Oversized square-shaped design
- Plastic frame, metal details on the sides
- Tinted lenses
Style Number/Barcode: 07008-0854

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty In Paradise Maxi Skirt
You'll be looking pretty on your next vacay to paradise in this adorable maxi skirt! It features a high-rise waist, a sultry thigh-high side slit, and a floor-length flowy silhouette. The knit fabric has a beautiful tropical floral print, perfect for a summer getaway. Style this skirt with a crop top and strappy sandals.

Fit & Features
- High-rise waist
- Thigh-high side slit
- Floor-length flowy silhouette
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 06501-0365

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Glam Tassel Earrings
Add some trendy glam vibes to your look with these gorgeous statement earrings. They feature a chain-link design with rhinestone embellishment and a chic tassel detail. Style these earrings with a curve-hugging midi dress and heels.

Fit & Features
- Chain-link design
- Rhinestone embellishment
- Tassel detail
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0872

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Fling Tassel Butterfly Earrings
Sweeten up your summer look with these tassel earrings! They feature a metal hoop, connected threaded tassels and a butterfly charm. Style them with a sundress and straw wedges.

Fit & Features
- Metal hoop
- Threaded tassels
- Butterfly charm
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07002-0797

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffle Me Up Midi Skirt
Flirty, flowy, and made for vacay vibes! This ruffle-trim midi skirt brings soft drama with a sleek fit and side slit that shows just enough—pair it with the matching top to complete the look.

Shop The Matching Top: Ruffle Me Up Crop Top

Fit & Features
- Smooth double-lined stretchy knit fabric
- High-rise waist
- Side ruched seam and ruffled slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000060

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Beach Please Floppy Hat
Have a stylish beach day in this chic floppy hat! It features an illusion stripe design. Pair it with a bikini and oversized sunglasses.

Fit & Features
- Illusion stripes
- Floppy design
Style Number/Barcode: 07302-0321

Category Name: Vacation Looks

Price: $6.97 $13.90

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