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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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.

Vip Treatment Snake Print One Piece Swimsuit
Get that VIP treatment in a little snake print! This one piece changes the game with a little strappy hip detail that we are obsessed with!

Fit & Features
- Scoop neckline
- Tank straps
- Removable padding
- Lattice strappy hip detailing
- Unique snake print pattern
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0208

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Total Doll Ruffle Mini Skirt
Step out looking like a fashion icon in this ruffle mini skirt, perfect for a haute night out! Pair with the matching top to complete the look.

Fit & Features
- Stretchy knit fabric
- Mid-rise waist
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Shop The Matching Top: Total Doll Halter Crop Top
Style Number/Barcode: 06501-000026

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Catch Me Poolside One Shoulder Braided Swim Top
Girl, make sure they catch you poolside in this fab swim top! Don't forget to pick up the matching bottoms for a completed look!

Shop Matching Bottoms: Catch Me Poolside Braided High Waist Swim Bottoms

Fits & Features
- Braided One Shoulder Strap
- Bandeau-Style Swim Top
- Removable Padded Bust
- Pull-On Design
- Matching Bottoms Sold Separate
Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0451

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Vibe Floral Swim Top
Your vacay looks are a total vibe! Pair this vibrant tropical floral swim top with the matching bottoms and get ready to relax under the palms!

Shop Matching Bottoms: Vacay Vibe Floral Swim Bottoms

Fit & Features
- Wrap neck | Back tie closure
- Front keyhole cut out
- Back hook closure
- All over tropical floral print
- Removable padding
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0348

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hot In The Tropics Tropical Bodycon Mini Dress
Walk around looking hot in this tropical bodycon mini dress while on a resort vacation or island destination!

Fit & Features
- Tropical palm print, knit fabric, stretchy knit lining
- Scoop neckline
- Spagehtti straps
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000101

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Vibe Floral Swim Bottoms
Your vacay looks are a total vibe! Pair these vibrant tropical floral swim bottoms with the matching top and get ready to relax under the palms!

Shop Matching Top: Vacay Vibe Floral Swim Top

Fit & Features
- High rise waist
- Ruched cheeky bottom
- All over tropical floral print
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0499

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tie Dye Frenzy Swim Bottoms
Brighten your summer with colorful tie-dye! These fun swim bottom keep it fab under the sun! Don't forget to pick up the matching top to complete your look!

Shop Matching Top: Tie Dye Frenzy Swim Top

Fit & Features
- Mid-Rise Fit
- Side Lattice Accents
- Ruched Back
- Cheeky Bottom
- Tie-Dye Pattern
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0599

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tie Dye Frenzy Swim Top
Brighten your summer with colorful tie-dye! This fun swim top keeps it fab under the sun! Don't forget to pick up the matching bottoms to complete your look!

Shop Matching Bottoms: Tie Dye Frenzy Swim Bottoms

Fit & Features
- V-Neckline
- Criss-Cross Strap Accent
- Adjustable Spaghetti Straps
- Removable Padding
- Tie Back Strap Accent
- Tie-Dye Pattern
- Built-In Flexible Boning
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0452

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Don't Underestimate Me Wired Swim Top
Don't underestimate a simple swimsuit babe! Dress it up with a gold chain belt and some stunner shades! Don't forge to pick up your matching swim bottoms!

Fit & Features
- Adjustable spaghetti straps
- Bar hook closure
- Molded cups
- Underwire
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0414

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tie Dye Kimono Sleeve Top
Add a splash of color to your OOTD with this tie top! If you got a beach day planned, we suggest pairing this over your bikini top and some denim cut-offs! For a casual outfit, a tube top with some high rise jeans would be so cute!

Fits & Features
- Quarter Length Kimono Sleeves
- Plunging V Neckline
- Tie Front Detail
- Mid-Length Hemline
- Textured Sheer Woven Fabric
- Relax Fit I No Stretch
Style Number/Barcode: 06204-0562

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Made For Sunny Dayz Black One Piece Bathing Suit
Babe you were made for sunny days, and your tan lewks so bomb when you wear a sleek black one piece and throw on those dark shades!!

Fit & Features
- One piece white swimsuit
- Adjustable spaghetti straps
- V neckline | Mesh inserts
- Cheeky bottom
- Mesh hip detailing
- Moderate stretch
- Padded
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0151

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fab In Floral Brushed Knit Maxi Dress
Walk right in like you own the place! This maxi dress features romantic florals throughout and a flowy, trailing skirt. Wear some bold earrings and block heels for a perfect 'fit!

Fits & Features
- Spaghetti Straps
- Square Neckline | Elastic Back
- Maxi Length Silhouette | Dual Front Slit
- Brushed Knit Fabric
- Form Hugging Fit | Plenty Of Stretch
- Zipper Not Featured
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0409

Category Name: Vacation Looks

Price: $9.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fresh Florals Flowy Chiffon Kimono
BB girl, you are the bouquet! Drape that casual OOTD with this flowy kimono for a spring-ready look!

Fits & Features
- Quarter-Length Sleeves
- Drape Open Front
- High-Low Hem
- Lightweight Sheer Chiffon Fabric I Floral Print
- Flowy Relax Fit
Style Number/Barcode: 06204-0267

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Stunner Lace Up Swimsuit
Aye babay you are a summer stunner in that sexy one piece swimsuit!

Fit & Features
- One piece design
- Lace up detail center bodice
- Adjustable spaghetti straps | Criss-cross back
- Built in padding
- Cheeky bottom
- Low back
- Ribbed detail | Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 07109-0178

Category Name: Vacation Looks

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hooked On Florals Crop Top
Get hooked on florals in this cute co-ord! Add some hoops and blocked heels and you'll be ready to take on the day! Make sure you add the matching bottoms to cart

Shop Matching Bottoms: Hooked On Florals Ruffle Trim Mini Skirt

Fits & Features
- Off Shoulder Neckline
- Fitted Long Sleeves I Elastic Cuffs
- 8 Rows Of Hook & Eye Closures Down The Front
- Crop Hemline
- Woven Textured Gauze Fabric I Lined At The Bust
- Moderate Stretch
- Matching Bottoms Sold Separately
Style Number/Barcode: 06003-0856

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chain Print Mesh Bodysuit
Amp up your look with this trendy chain print neon mesh bodysuit! A must for your festival season 'fit!

Fit & Features
- Adjustable spaghetti straps
- Sweetheart neckline
- Wired cups
- Low scoop back with hortizonal adjustable back strap
- Thong bottom | Dual hook and eye closures
- Sheer stretchy mesh fabric
- All over chain print
Style Number/Barcode: 06001-2646

Category Name: Vacation Looks

Price: $11.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Catch Flights Tropical Lace-Up Slit Maxi Dress
Booked the trip just for the outfit? Valid. This lace-up back maxi brings the heat with a tropical print and a leg-baring high slit that knows how to make an entrance.

Fit & Features
- Smooth knit stretchy fabric, tropical print, soft knit stretch lining
- Square neckline with spaghetti straps
- Bodycon silhouette
- Lace-up open back with tie closure
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000005

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Vibes Chiffon Kimono
Bring on those tropical vibes in this perf kimono for a little getaway! Layer over your fave swimsuit and get ready to soak up the sun.

Fit & Features
- Long kimono style sleeves
- Drape open front
- High low hem
- Tropical floral and palm print
- Woven chiffon fabric
Model is 5'6" with a 33" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-0258

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hooked On Florals Ruffle Trim Mini Skirt
Get hooked on florals in this cute co-ord! Add some hoops and blocked heels and you'll be ready to take on the day! Make sure you add the matching top to cart

Shop Matching Top: Hooked On Florals Crop Top

Fits & Features
- High Rise Waist
- 8 Rows Of Hook & Eye Closures Down The Front
- Mini Length Silhouette I Ruffle-Trim Hemline
- Cinched At Center Back
- Fully Lined Textured Gauze Fabric
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 06401-0227

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chiffon Tropical Floral Maxi Dress
You are bronzed and ready for vacay in this goddess-like tropical maxi dress!

Fit & Features
- V-neckline
- Spaghetti straps
- Drop shoulder detailing
- Long maxi hemline
- Chiffon material | Minimal stretch
- Tropical floral pattern
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0036

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Playful Petals Floral Chiffon Off Shoulder Mini Dress
Let your feminity show and flow in this darling mini dress!

Fits & Features
- Off Shoulder, Foldover Neckline
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette I Detachable Waist Tie I Wrap Skirt
- Chiffon Lined Fabric
- Moderate Stretch
Style Number/Barcode: 05101-0464

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Star Potential Satin One Piece Swimsuit
Bb you are star potential in this sexy one piece! Take it to the next level and pair with some strappy heels and cay eye sunnies. O-M-G fire.

Fit & Features
- One piece
- Deep v neckline
- Tank straps
- Triangular hip cut out
- High waist
- Open back | Bar hook closure
- Satin like sheen | Moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0168

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Butterfly Babe Jelly Sandals
These jellies are giving us major butterflies bby! These pretty sandals are perfect to pair with a pair of cut-off shorts and cute crop!
- T-Strap
- Large Irredscent Butterfly Accent
- Adjustable Sling Back Strap
- Jelly Insole
Style Number/Barcode: 07404-0590

Category Name: Vacation Looks

Price: $18.90

Availability: Out of Stock
Product Badge:
- Ships Free
Flower Girl Lace Up Crop Top
Girl, you've got that flower power for sure! Pair this adorable ditsy floral crop top with some light wash jeans and strappy mules for a too cute vibe.

Fit & Features
- Off the shoulder square neckline
- Short sleeves
- Lace up front
- Cropped
- Stretchy smocked fabric
- All over ditsy floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2210

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials