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.

Floral Ditsy Smocked Tie Front Mini Dress
Spring into a smocked disty mini dress to keep on trend this season. This flirty piece features a sweetheart neckline, a tie front with a small keyhole at the bust, and an all-over floral ditsy print. The relaxed fit bodice leads to a curve-hugging mini-length silhouette. The dress is composed of a smocked knit fabric that offers a moderate stretch. Complete your look with hoop earrings and minimal heels.

Fit & Features
- Sweetheart neckline
- Keyhole at bust
- Floral ditsy print
- Smoked fabric
- Form-hugging fit
- Moderate stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0497

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweetheart Neck Ruffled Ditsy Print Mini Dress
Keep on trend in a floral ruffle dress. The ditsy floral dress features a sweetheart neckline, ruffled shoulder straps and an-all over ditsy floral print. The relaxed fit waist leads to a mini length silhouette that offers a curve-hugging fit with slight stretch. Complete your outfit with hoops and dad sneakers for a casual vibe.

Fit & Features
- Sweetheart neckline
- Ruffled shoulder straps
- Ditsy floral print
- Mini length silhouette
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0538

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Gimme Shade Cat Eye Sunglasses
Throw some serious shade in sunglasses that bring the extraness to your outfit. The sunglasses feature a flat top, a cat-eye shaped frame, and a tortoise-shell pattern throughout. Complete look with a curve-hugging bodycon dress and heels for the perfect brunch-ready outfit.

Fit & Features
- Cat-eye shaped frame
- Tortoise-shell pattern
- Dark lenses
- Wide hard plastic arms
Style Number/Barcode: 07008-0797

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Two Pack Butterfly Hair Clips
Give them butterflies with hair clips that bring the charm. The two-pack features 3-D butterfly embellished hair clips to create gorgeous updos or statement side parts. Complete your fluttery look with a floral sundress and open-toe mules.

Fit & Features
- Two-pack
- Gold 3-D butterfly design
Style Number/Barcode: 07006-0189

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All the Shade Over-Sized Cat Eye Sunglasses
Bring the shade in fab sunglasses that elevate your looks. The sunglasses feature an over-sized cat-eye frame, dark lenses, and sleek metal arms. Complete look with a wide-leg jumpsuit and rhinestone studs.

Fit & Features
- Over-sized cat-eye frames
- Dark lenses
- Sleek metal arms
Style Number/Barcode: 07008-0798

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Energy Strapless Crop Top
Bring the energy to your destination getaway in this tropical crop top, designed with a sleek strapless neckline and fitted hem. Pair it with the matching skirt.

Fit & Features
- Tropical print, mesh fabric, soft knit stretchy lining
- Strapless neckline
- Fitted crop hem
- Runs true to size
Shop The Matching Skirt: Tropical Energy High-Rise Midi Skirt
Style Number/Barcode: 06001-000053

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Gurl Jelly Rhinestone Bow Sandals
Show off your sweet side gurrrrrrl!! These cute clear sandals are perfect for a day by the pool, feelin' fab and living it up!
- Open round toe
- Thong design with bow detail
- Rhinestone trim
- Composed of transparent jelly
Style Number/Barcode: 07404-0634

Category Name: Vacation Looks

Price: $10.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Strapless Ruffled Ditsy Romper
Bring the charm in a floral romper to make a sweet impression. The romper features a straight strapless neckline with a ruffled popover accent and an all-over ditsy floral print. Complete your brunch-ready outfit with a pair of cork wedges and layers of dainty jewelry.

Fit & Features
- Sleeveless straight neckline
- Ruffled popover accent
- Ditsy floral print
- Wide-leg shorts
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06303-0095

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Frilled and Flirty Off The Shoulder Smocked Crop Top
Keep it flirty in this frilly crop top to make a sweet impression. This cute top features an off the shoulder neckline, a smocked bodice, and ruffled hem. Complete your casual date night or create a chic festival outfit with a pair of your favorite high waist jeans and a dainty necklace.

Fit & Features
- Ruffled off the shoulder neckline
- Smocked bodice
- Long sheer chiffon sleeves
- Cropped hem with ruffle trim
- Relaxed fit
- Moderate stretch
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06003-0574

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sporty Cork Platform Sandals
Give your summer look a sporty finish when you step out in these cuties! Style them with cut off denim and a white tee!

Fit & Features
- Open almond toe
- Single-band over the toe
- Slingback + ankle strap
- Faux leather
- Cork platform
- Rigged sole
Style Number/Barcode: 07404-0554

Category Name: Vacation Looks

Price: $5.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
A Sparkling Finish Dainty Double O-Ring Belt
Finish your look with just a little bit of glam! Keep your vibe sleek and polished when you pair this belt with high waist black bottoms, and a sleek black bodysuit!
- Thin design
- Dainty O-ring rhinestone buckle
- Adjustable ball point closure
- Faux leather
Style Number/Barcode: 07301-0158

Category Name: Vacation Looks

Price: $5.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Ruffled Chiffon Skater Dress
Bring the charm in a ruffled dress that gets those tropical island vibes just right! This vacay-approved dress features a tropical palm-leaf print, a plunging V neckline, ruffled shoulder straps, a cinching tie waist belt, and a flirty skater silhouette. Complete the outfit with pretty wedge heels and fringe earrings.

Fit & Features
- Tropical palm-leaf print
- Plunging V neckline
- Ruffled shoulder straps
- Tie waist belt
- Open back with tie back ties
- Lower back zipper and hook and eye closure
- Skater silhouette
- Sheer chiffon fabric with a woven lining
- Runs true to size
Style Number/Barcode: 05102-0264

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casually Chic Nubuck Platform Wedges
Keep it casually cute in wedges to style with sundresses this season. Step out for brunch in these wedges that feature an open back, an adjustable ankle strap, and a low platform to elevate looks.

Fit & Features
- Open almond toe
- Adjustable ankle strap
- Wide single strap over the toe
- Low platform
- Nubuck material
Style Number/Barcode: 07406-0060

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Luxe Life Quilted Chevron Crossbody
Keep it luxe with a chevron crossbody that elevates your date-night looks. The versatile crossbody features a quilted chevron body, a top zipper closure with tassel accent, and a chain with faux leather shoulder strap. Complete your look with a bodycon dress and clear heels.

Fit & Features
- Quilted chevron body
- Top zipper closure
- Tassel
- Faux leather
- Chain and faux leather shoulder strap
Style Number/Barcode: 07203-0297

Category Name: Vacation Looks

Price: $8.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keeping It Casual Tassel Kimono
Keep it casual in a cute kimono. This layer-worthy piece features a draped open front, kimono sleeves, and a georgette tassel detail at the hem. Complete look with cut-off shorts and stylish sunglasses.

Fit & Features
- Draped open front
- Kimono sleeves
- Georgette tassel detailed hem
- Sheer lightweight woven fabric
- Relaxed fit
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06204-0527

Category Name: Vacation Looks

Price: $8.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Passion Chiffon High Low Kimono
Bring a burst of florals in a kimono to layer with all your favorite looks. The kimono features a draped open front, an-all over floral print, long kimono sleeves, and a high low hem. Use this kimono as a coverup to layer over swimsuit or style with high waist shorts and a basic top.

Fit & Features
- Draped open front
- Long kimono sleeves
- Floral print
- High-low hem
- Sheer chiffon fabric
- Relaxed fit
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-0256

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Long Sleeve Mesh Crop Top
Bring the tropics in this crop top that will transport you to a floral paradise. The top features a sheer unlined mesh fabric, a tropical floral print, and a cropped hem. Complete look with high waist shorts and cork wedges.

Fit & Features
- High round neckline
- Fitted long sleeves
- Tropical floral print
- Cropped hem
- Sheer unlined mesh fabric
- Relaxed fit, moderate stretch
- Pasties/undergarments sold separately
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2420

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Dreams Floral Romper
You need this romper for your next getaway! Pair it strappy sandals and a straw hat for a insta worthy look.

Fits & Features
- All Over Floral Print
- Strapless
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06503-0237

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Gaze Sleeveless Romper
Gaze on at this cute pattern girl! Pair this season-ready romper with a pretty wedge and sleek hoops for a complete look!

Fit & Features
- V-Neckline
- Adjustable Spaghetti Straps | Cross-Back Straps
- Lined Floral Lace Bodice
- Unlined Crochet Waist Trim
- Floral and Paisley Pattern Wide Leg Shorts
- Gauze Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 06303-0089

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunny Oasis Ruffle Mini Skirt
Escape to a sunny destination with this alluring high-rise ruffle mini skirt! Pair with the matching top to complete the trendy vibe.

Fit & Features
- Slinky knit stretchy fabric
- High-rise waist
- Bodycon silhouette
- Side ruched seams
- Ruffled mini-length hem
- Runs true to size
Shop The Matching Top: Sunny Oasis Halter Crop Top
Style Number/Barcode: 06501-000053

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bring On The Boho Vibes Printed Pants
Bring on the major boho babe vibes in these printed wide leg pants! Pair with a crochet top and a trendy panama hat!

Fit & Features
- High rise waist
- Back zipper closure
- Flowy wide pant legs
- All over detailed boho striped print
- Woven gauze fabric | No stretch
Style Number/Barcode: 06302-0118

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Zebra Print High Slit Maxi Skirt
Give your summer look a wild vibe in this sassy zebra print high slit maxi skirt! Pair with a simple top and some heels and let the skirt be the major statement.

Fit & Features
- High rise elastic banded waist
- Wrap front with high slit
- Cheeky bodysuit bottoms
- Flowy maxi length
- Stretchy knit fabric
- All over zebra and animal prints
Style Number/Barcode: 06501-0220

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
High Waist Floral Ruched Mini Skirt
Spring into florals in a fab mini skirt. Dress up your basic tops with a floral mini skirt that features a flattering high rise waist, ruched side seams with drawstring ties, and an all-over floral print. The skirt is composed of a smooth knit fabric that enhances curves with a moderate stretch. Complete your outfit with strappy heels and a dainty necklace for a brunch-ready look.

Fit & Features
- High rise waist
- Ruched side seam with drawstring ties
- Floral print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06501-0263

Category Name: Vacation Looks

Price: $8.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tie Dye Cut Out Racer Neck Romper
A tie-dye romper brings the retro vibes. Hit your next festival in this fun tie-dye romper that impresses with sexy cutouts at bust through the mid-drift, a halter neck to show off shoulders, and a daring lower back cutout. The relaxed fit waist leads to a pair of flowy wide-leg shorts. Complete your look with statement wedges and extra-large hoops.

Fit & Features
- Halter neck with racer bust
- Cut out at the center of the bodice
- Mid-drift cut out with criss-cross strap accents
- Tye-dye print
- Wide-leg shorts
- Lower back keyhole with drawstring straps
- Lightweight knit fabric
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06503-0123

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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