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

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

Rhine On The Horizon Slide Sandal
Can you see these glam rhinestone sandals on the horizon? They feature an on-trend square toe, dual PVC straps, rhinestone trim, and a slide-on/off styling. Complete the look in lace bustier and skinny jeans.

Fit & Features
- Square toe
- Dual PVC straps
- Rhinestone trim
- Slide-on/off styling
- Runs true to size
Style Number/Barcode: 07404-0971

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sassy Stripes Knit Halter Top
Show off your sassy side with a halter top that brings the style! The top features a stylish striped pattern, a halter neck with adjustable neck ties, triangle cups, and a cropped hem. The top is composed of an unlined knit fabric that offers a form hugging fit with minimal stretch. Complete look with distressed shorts.

Fit & Features
- Halter neck
- Adjustable neck ties
- Triangle cups
- Stripped pattern
- Cropped hem
- Unlined knit fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06005-1217

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sandy Beaches Boho Halter Top
The perfect boho top to walk the sandy beaches in while on vacay! It features a sleeveless, halter neck with tie, cropped hem, and an open back with tie closure on boho-inspired print on woven fabric. Complete the look in the matching top.

Shop Matching Bottoms: Sandy Beaches Boho Wide Leg Pants

Fit & Features
- Sleeveless, halter neck, tie closure
- Cropped hem
- Open-back with tie
- Boho-inspired print
- Woven lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1591

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sandy Beaches Boho Wide Leg Pants
The perfect boho pants to walk the sandy beaches in while on vacay! They feature a high-rise elasticized waist, flowy, wide-leg silhouette, and a boho-inspired print on woven fabric. Complete the look in the matching top.

Shop Matching Top: Sandy Beaches Boho Halter Top

Fit & Features
- High-rise elasticized waist
- Wide-leg silhouette
- Boho-inspired print
- Woven lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0619

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Back To Shore Crochet Cover Up Dress
You'll love this crochet cover up dress to pack with you on every vacation or beach day! With a plunge neckline with a chic hoop insert and form-hugging fit, this dress is perfect for layering over a swimsuit.

Fit & Features
- Sheer crochet knit fabric
- Long sleeves, flare cuffs
- Plunge neckline, hoop insert
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000054

Category Name: Vacation Looks

Price: $39.90

Availability: Out of Stock
Product Badge:
- Ships Free
Never Gets Old Denim Distressed Shacket
This denim shacket will always be a staple in your closet! It features long sleeves with button cuffs, a collared neckline, a button-down front, flap pockets, and an oversized fit with distressed accents. Complete the look in a sleek mini dress and booties for a stylish lunch date.

Fit & Features
- Long sleeves, button cuffs
- Collared neckline
- Button-down front
- Flap pockets
- Oversized fit, distressed accents
- Light wash denim, no stretch
- Fits true to size
Style Number/Barcode: 06203-0476

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Finish The Race Checkered Tank Top
Finish the race and win big in style points! This checkered tank top brings the edge you need to stay ahead of the trends. It features a sleeveless square neckline, tank straps with hoop insets, and a curved, cropped hem. Complete the look in distressed shorts.

Fit & Features
- Sleeveless, square neck
- Tank straps with hoop insets
- Curved, cropped hem
- Checkered print
- Knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4136

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Romance Chiffon Surplice Top
Get caught up in a floral romance with this top that brings the charm. The top features a floral print, a plunging wrap V-neckline, long sleeves, and tie-back ties at the hem. The top is composed of a semi-sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with high waist jeans and mules.

Fit & Features
- Floral print
- Wrap V-neckline
- Long sleeves
- Tie-back accents at hem
- Semi-sheer chiffon fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06003-1777

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Chic Lace Up Top
Channel your bohemian side with a top that will have you festival ready! The top features a bohemian print, a sleeveless square neckline, spaghetti straps that lead to a cross-back design, and a cropped hem. The top is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching maxi skirt.

Shop Matching Maxi Skirt: Bohemian Chic Maxi Skirt

Fit & Features
- Bohemian print
- Sleeveless square neckline
- Spaghetti straps
- Lace-up back
- Cropped hem
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3747

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Chic Maxi Skirt
Channel your bohemian side with a skirt that will have you festival ready! The skirt features a bohemian print, a high rise waist, and a maxi length with a high side slit. The skirt is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching crop top.

Shop Matching Crop Top: Bohemian Chic Lace Up Top

Fit & Features
- Bohemian print
- High rise waist
- Maxi length
- High side slit
- Lined smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0538

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Day & Night Crepe Tie Strap Romper
The perfect crepe romper to wear for day and night plans! It features a sleeveless, sweetheart neck, tie straps. and a form-fitting bodice atop flowy shorts. Complete the look in flirty heels.

Fit & Features
- Sleeveless, sweetheart neck, tie straps
- Form-fitting bodice
- Flowy shorts
- Crepe-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-0958

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Paradise Awaits Mesh Duster
Get ready for your getaway to paradise with this breezy lightweight mesh duster. It features long fitted sleeves, an open front, a mid-length flowy silhouette, and an all-over palm leaf print. Layer this duster over your fave bikini and complete the look with chic shades.

Fit & Features
- Long fitted sleeves
- Open front
- Mid-length flowy silhouette
- Palm leaf print
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0324

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Country Road Lace Tie-Front Top
Hit up the open country roads in this lace tie-front top for a little country romance! The crop top features 3/4 length kimono sleeves, a plunge neckline, and a tie-front detail along the cropped hem. Complete the look in a chic panama hat and denim shorts.

Fit & Features
- 3/4 length kimono sleeves
- Plunge neckline
- Tie-front detail
- Cropped hem
- Sheer lace trim
- Fits true to size
Style Number/Barcode: 06204-1248

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Palm Leaf Maxi Skirt
Hit the tropics in a maxi skirt that is ready for those island vibes! The skirt features a palm leaf print, an elastic high rise waist, a high side slit, and a maxi length silhouette. The skirt is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching crop top.

Shop Matching Crop Top: Tropical Palm Leaf Crop Top

Fit & Features
- Tropical palm leaf print
- Elastic high rise waist
- High side slit
- Maxi length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0540

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Bell Paisley Off-The-Shoulder Top
Set the trend for the festival season! This boho paisley top features an off-the-shoulder neckline with long bell sleeves and an elastic cropped hem. Composed of woven linen fabric with no stretch. Finish the look in a mini skirt.

Fit & Features
- Off-the-shoulder neckline
- Long bell sleeves
- Elastic cropped hem
- Paisley pattern
- Woven linen fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1712

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Palm Leaf Crop Top
Hit the tropics in a crop top that is ready for those island vibes! The crop top features a palm leaf print, a plunging sleeveless V-neckline, a ruched drawstring, spaghetti straps, and a cropped hem. The top is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching maxi skirt.

Shop Matching Maxi Skirt: Tropical Palm Leaf Maxi Skirt

Fit & Features
- Tropical palm leaf print
- Sleeveless V-neckline
- Ruched drawstring
- Spaghetti straps
- Cropped hem
- Lined smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06001-3752

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
A Total Vibe Halter Bodysuit
You in this sultry-chic bodysuit would be a total vibe! Featuring a sleeveless twist-front halter neckline with a center keyhole cutout at the bust, this bodysuit will elevate your basic look. Style with a faux leather skirt and mules.

Fit & Features
- Sleeveless twist-front halter neckline
- Center keyhole cutout
- Open back
- Thong bottom, dual snap-button closure
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4271

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Colette Formal Ruched Midi Dress
Special Occasion

Create a stunning impression with a formal bodycon that is the perfect choice for your cocktail affair! Colette features a sleeveless wired sweetheart neckline, ruching throughout to enhance curves, a sexy cutout at the midriff for a hint of skin, and a midi-length silhouette accented with a high center slit. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a sphere clutch and rhinestone earrings.

Fit & Features
- Sleeveless wired sweetheart neckline
- Adhesive bra friendly
- Ruching, cutout at the midriff
- High waist
- Bodycon
- Midi length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05001-0960

Category Name: Vacation Looks

Price: $29.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweetest Style Lace-Up Eyelet Skater Dress
Show off the sweetest style at your weekend plans in this airy eyelet skater dress! Designed with a lace-up bust and fit-and-flare silhouette, pair with a charm necklace.

Fit & Features
- Woven eyelet fabric
- Sleeveless square neckline, lace trim, lace-up bust design
- Pleating at the bodice, back zipper closure
- Thin adjustable tank shoulder straps
- High waist seam
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3951

Category Name: Vacation Looks

Price: $49.90

Availability: In Stock

Available Color: WHITE

Available Size: XS, S, M, L, XXS
Fiercely Chic Leopard Bikini Top
Make a fierce impression chic impression with a bikini top that shows off your wild side! The bikini top features a leopard print, demi cups with underwire, adjustable spaghetti straps, and a slide-hook closure at the back. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Fiercely Chic Leopard Bikini Bottoms

Fit & Features
- Leopard print
- Demi cups, underwire
- Adjustable spaghetti straps
- Slide hook closure at back
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0649

Category Name: Vacation Looks

Price: $4.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Strap Up PU Knotted Block Heels
Strap up for a night on the town in these block heels featuring a trendy, lace-up on a square toe with knotted accents. Complete the look in a sultry club dress.

Fit & Features
- Square toe
- Block heel
- Lace-up design with tie closure
- PU faux leather material
- Runs true to size
Style Number/Barcode: 07401-3781

Category Name: Vacation Looks

Price: $12.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bronzed Beauty One-Piece Swimsuit
Showcase your beauty as you relax poolside in this sultry one-piece! The swimsuit features a wrap-front design with halter straps with a tie-back closure, a front waist cutout, an open back with a lower back strap, and a high-cut, semi-cheeky fit. Style with chic sunglasses.

Fit & Features
- Wrap-front design
- Halter straps, tie closure
- Front waist cutout
- Open back, lower back strap
- High-cut, semi-cheeky fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0291

Category Name: Vacation Looks

Price: $4.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Comfort Slides Criss-Cross Sandals
Slide into the comfort of these sandals featuring PU criss-cross straps, a slight platform sole, and a soft footbed. Complete the look in a cute lounge set for a coffee run.

Fit & Features
- PU criss-cross sandals
- Slight platform sole
- Soft footbed
- Slide-on/off styling
- Runs true to size
Style Number/Barcode: 07404-1029

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Style Icon Faux Leather Block Heels
Step out like the style icon you are in these heels slay! The heels feature an open back, an open square toe, a multi-strap caged design over the toe, lace-up ties, and a block heel. The heels are composed of faux leather material. Complete look with a bodycon for a GNO.

Fit & Features
- Square toe
- Multi-strap caged design
- Lace-up ties
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3779

Category Name: Vacation Looks

Price: $36.90

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