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

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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.

Precious In Faux Pearl Flat Sandals
Look and feel precious in these chic flat sandals perfect for slipping on while getting ready for a formal wedding or styling for a dressy date! They feature a square toe, and a wide strap with faux pearl insets, and are composed of an ultra-soft faux suede material. Complete the look with a hair clip to create a cute updo!

Fit & Features
- Square toe
- Wide strap with faux pearl insets
- Flat sole
- Ultra-soft faux suede material
- Runs true to size
Style Number/Barcode: 07404-1136

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendsetting Style Chain Strap Mini Dress
Show off your trendsetting style in this sleeveless bodycon mini dress! It features a scoop neckline, adjustable spaghetti straps with chunky chain-link accents, a mini-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Complete the look in this short dress with a mini handbag and clear mules.

Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps, chain-link accents
- Mini-length hem
- Form-hugging fit
- Stretchy ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4917

Category Name: Vacation Looks

Price: $5.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pristine Chic Bandage Midi Skirt
Keep your style pristine and chic in this must-have bandage midi skirt featuring a smooth high-rise fit and a bodycon silhouette. The skirt is designed with a specialty bandage-seamless knit fabric that hugs your body like a glove! Complete the look in a lace-bustier and oversized blazer for dinner and drinks.

Fit & Features
- Smooth high-rise fit
- Bodycon silhouette
- Midi-length hem
- Bandage-seamless knit design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0839

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sun Seeker Sheer Crochet Kimono
Layer on the cute and relaxed vibes of this sheer crochet kimono perfect for pool parties, beach days, or vacations!

Fit & Features
- Sheer crochet fabric
- Slouchy long sleeves
- Open front design
- Relaxed silhouette
Style Number/Barcode: 06204-2071

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Cotton V-Neck Crop Top
Let the sunshine on your shoulders in this cotton crop top for your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a center front drawstring along the cropped hem, and a back smocked panel. Complete the look in a mini skirt and sandals.

Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Center front drawstring
- Cropped hem
- Back smocked panel
- Lined cotton fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1905

Category Name: Vacation Looks

Price: $11.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Biker Chick Cropped Graphic Tee
Edge up your look with this trendy cropped graphic tee! It features a crew neckline with a notched front, short sleeves, a tie-front design, a skull and wings graphic with the script, "Motorcycle," and a fitted cropped hem. Complete your biker chick look with a fringe skirt and cowboy boots.

Fit & Features
- Crew neckline, notched front
- Short sleeves
- Tie-front design
- Skull and wings graphic, script that reads, "Motorcycle"
- Fitted cropped hem
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1516

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
GNO Denim Corset
Step out for GNO in a stunning corset that stuns! The corset features a sleeveless sweetheart neckline, adjustable shoulder straps, padded demi-cups, flexible boning, and a hook and eye front closure. The corset is composed of a lined denim fabric that offers a form hugging fit with a moderate stretch. Complete look with a wrap skirt.

Fit & Features
- Sleeveless sweetheart neckline
- Padded demi cups
- Flexible boning
- Hook and eye front closure
- Cropped hem
- Lined denim fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06003-1684

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Find Balance Ying Yang Graphic Crop Tee
Find your balance with this graphic tee to add to your weekly rotation! It features short sleeves, a crew neck, a front ying yang graphic, and a raw-cut cropped hem on cotton fabric. Complete the look in denim shorts for a casual hang with friends!

Fit & Features
- Short sleeves, crew neck
- Front ying yang graphic
- Raw-cut, cropped hem
- Relaxed fit
- Soft and stretchy cotton fabric
- Runs true to size
Style Number/Barcode: 06002-1509

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweet And Chic Paperbag Shorts
Sweet and chic, these dressy paperbag shorts will elevate your everyday looks. They feature a high-rise waist, a tie-front belt, front pockets, and a relaxed fit. Style with a basic bodysuit or a cute cropped blouse.

Fit & Features
- High-rise elasticized paperbag waist
- Tie-front belt
- Front pockets, single faux back pocket
- Relaxed fit
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0287

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Nail The Trend Swirl Print Sweater Dress
Make heads turn in this on-trend sweater dress to show off your new spring style! It features a sleeveless square neck, adjustable spaghetti straps, a bodycon silhouette, and a midi-length hem on swirl print knit fabric. Complete the look in sandals for a backyard party!

Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Swirl print
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1671

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Starstruck Glitter Mesh Mini Dress
You'll leave them starstruck by your beauty in this glitzy glitter mesh mini dress! It features a sleeveless V-neckline with a dainty ruffled trim, spaghetti straps, all-over ruching, a mini-length ruffled hem with a front adjustable drawstring, and a curve-hugging silhouette. The sheer glitter mesh fabric includes a full knit lining. Style with metallic heels.

Fit & Features
- Sleeveless V-neckline, ruffled trim
- Spaghetti straps
- All-over ruching
- Mini-length ruffled hem, front adjustable drawstring
- Curve-hugging fit
- Sheer glitter mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1873

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Free Spirited Paisley Tie-Back Crop Top
Calling all free-spirited babes! This crop top is perfect for festivals and your warm-weather closet. It features adorable puff short sleeves, a scoop neck, and a flirty tie-back on woven fabric with a boho paisley-floral print. Complete the look in trendy denim shorts.

Fit & Features
- Puff short sleeves
- Scoop neck
- Cropped hem
- Tie-back design
- Paisley-floral print
- Non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 06003-1924

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty And Bold Floral Jelly Sandals
Pretty and bold, these floral jelly sandals add a casual-chic vibe. They feature a square-shaped toe, a wide toe strap with a floral pom design, an open back for easy on-and-off styling, and a flat sole for comfortable wear. Style with a mini handbag.

Fit & Features
- Square-shaped toe
- Wide toe strap
- Floral pom design, faux leather material
- Open back
- Flat sole
- PVC material
- Runs true to size
Style Number/Barcode: 07404-1126

Category Name: Vacation Looks

Price: $8.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
In Spring Floral Block Heel Mules
Get in the spring of things in these fresh and flirty floral mules to elevate every outfit this season! They feature a square toe, dual straps with floral accents, and a block heel, and are composed of faux leather material. Complete the look in a cute short dress for a graduation ceremony or birthday!

Fit & Features
- Square toe
- Dual straps with floral accents
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4134

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Level Up Your Look Cargo Mini Skirt
Level up your cute and casual everyday look with this of-the-moment cargo mini skirt. It features a high-rise waist with belt loops, a front button closure, back pocket flaps, cargo-style side pockets with adjustable straps and buckles, a mini-length hem, and a form-hugging fit. Style with a corset top and clear mules.

Fit & Features
- High-rise waist, belt loops
- Front snap-button closures, hidden zipper closure
- Back faux flap pockets
- Cargo-style side pockets, adjustable straps, buckles
- Mini-length hem, form-hugging fit
- Twill denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0153

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cute In Chevron Print Mesh Flare Pants
You'll look cute in these chevron print pants for festival season or hitting up the country bar! It features a high-rise elasticized waist, a hip-hugging fit, and a flared hem. The semi-sheer mesh fabric features a built-in knit panty lining. Complete the look with the matching top.

Shop Matching Top: Cute In Chevron Print Mesh Crop Top

Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flared hem
- Chevron print
- Mesh fabric, knit panty lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-2248

Category Name: Vacation Looks

Price: $5.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Slay Tropical Print Midi Dress
Slay your vacay look with this curve-hugging tropical print midi dress! It features a sleeveless V-neckline, spaghetti straps, a ruched side seam, a midi-length asymmetric hem creating a chic side slit, and a bodycon silhouette. The all-over tropical palm leaf print will really bring those vacay vibes. Complete the look with clear mules.

Fit & Features
- Sleeveless V-neckline, spaghetti straps, bust lining
- Ruched side seam
- Midi-length asymmetric hem, side slit
- Bodycon silhouette
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4948

Category Name: Vacation Looks

Price: $5.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Eyes on You Abstract Print Cutout Mini Dress
You didn’t just enter the room—you owned it. With a bold cutout and curve-hugging fit, this iconic abstract print mini dress is your go-to for nights out where the vibe is flirty and fearless.

Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless sweetheart neckline, padded bra cups
- Bust cutout with lattice design, large waist cutout
- Adjustable spaghetti straps
- Ruching, mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000288

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: BLUE

Available Size: XS, S, L
Product Badge:
- Sale
Dream Escape Tropical Midi Dress
Pack right for your dream escape with this tropical print midi dress perfect for a dinner with a beachside view! It features a sleeveless V-neckline, adjustable spaghetti straps that crisscross in the back, a bodycon fit, and a ruched side seam to accentuate your curves atop a sultry slit. The smooth knit fabric features a gorgeous tropical floral print that will give off major vacay vibes. Complete the look with sleek earrings and a choker necklace.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, crisscross back
- Bodycon silhouette
- Side ruched seam, slit accent
- Asymmetric midi-length hem
- Tropical floral print, knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4957

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Style In Check Utility Denim Romper
Keep your style in check and looking fresh in this denim utility romper perfect for weekend road trips or exploring downtown! It features short sleeves, a collar neckline, front zipper closure, flap pockets, a belted waist with buckle closure, a short-length hem, and a form-hugging fit. Complete the look in trendy sandals.

Fit & Features
- Short sleeves, collar neckline
- Front zipper closure
- Belted waist, buckle closure, belt loop accents
- Chest flap pockets
- Short-length hem
- Medium-wash denim fabric, moderate stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0322

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
That 70s Chick Retro Print Crop Top
Inspired by the groovy era, you'll look like a cute chick in this retro crop top perfect for parties! It features a sleeveless bodice, convertible shoulder straps that can be worn in multiple ways, a fitted, cropped hem, and a geometric-retro print design. Complete the look with high-rise denim and platform heels.

Fit & Features
- Sleeveless bodice
- Convertible shoulder straps, multiple ways to wear
- Fitted, cropped hem
- Geometric-retro print design
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4740

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend Mode Basic Strap Sandals
Get into a chill weekend mode with these basic strap sandals. They feature an almond-shaped toe, a wide banded toe strap, adjustable ankle and heel straps, and a flat sole for comfortable wear. Style with a crop top and denim shorts.

Fit & Features
- Almond-shaped toe
- Wide banded toe strap
- Adjustable ankle and heel straps
- Buckle detail
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1076

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In Paradise Tropical Print Midi Dress
You'll be ready for your paradise getaway with this tropical print midi dress! It features a sleeveless V-neck, spaghetti straps, a sultry cutout back, a bodycon silhouette, and an asymmetrical side slit cutout. Complete the look in wedges.

Fit & Features
- Sleeveless V-neck, spaghetti straps
- Cutout back
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Tropical print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4987

Category Name: Vacation Looks

Price: $19.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Festival Fun Crochet Tie-Back Crop Top
Make your mark at festivals this season in this crochet knit crop top featuring bell long sleeves, a plunge V-neck, and a sassy open back with tie closure. Style with high-rise denim shorts for a trendy look!

Fit & Features
- Bell long sleeves
- Plunge V-neck
- Cropped hem
- Open back with tie closure
- Crochet knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06001-4627

Category Name: Vacation Looks

Price: $6.97 $36.90

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