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.

Sweet Flair High Slit Ditsy Floral Knit Midi Dress
Bring the sweet flair to date night in this high slit ditsy floral midi dress! The all-over ditsy floral print on the stretchy knit fabric is the perfect amount of sweetness with the sultry details of the mid-length dress. The sleeveless scoop neckline features a tie-front at the bust for a cute touch, spaghetti straps, an alluring thigh-high side slit to showcase some leg, and a slim-fit silhouette to showcase your figure. Style this midi dress with a faux leather jacket and heels!

Fit & Features
- Ditsy floral print, stretchy knit fabric
- Sleeveless scoop neckline with bust tie
- Spaghetti straps
- Thigh-high side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5485

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Breeze Tropical Cutout Slit Maxi Dress
Feel the island breeze in this tropical maxi dress while on vacation! With a square neckline, spaghetti straps, and a form-hugging fit, this maxi dress is perfect for a day in the sun. The cutout bodice and high front slit add a touch of playfulness to your island look. Complete the look with sandals.

Fit & Features
- Tropical palm print, smooth stretchy knit fabric, sewn-in knit lining
- Square neckline
- Spaghetti straps
- Cutout bodice, high slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5670

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Catching Looks Crochet Bandeau Tube Top
Serving body and beach energy all in one slay. This crochet bandeau tube top features a strapless sweetheart neckline and chic tie-front design, perf for sipping cocktails, catching sunsets, or just catching looks.

Shop Matching Bottoms: Catching Looks Crochet Palazzo Pants

Fit & Features
- Sheer textured crochet fabric with lining
- Strapless sweetheart neckline
- Flow tie-front design at the bust
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06003-000048

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wish On A Rhinestone Starfish Straw Flat Sandals
Step into summer with these playful straw flat sandals. Featuring a round toe and wide strap adorned with rhinestone starfish and decor, you'll feel like a mermaid strolling on the beach! Complete the look with sunnies.

Fit & Features
- Flat sole
- Round toe
- Rhinestone embellished starfish and decor
- Straw with metallic woven threads material
- Runs true to size
Style Number/Barcode: 07404-1230

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sensational Match Bodycon Midi Skirt
Make a sensational impression in this bodycon midi skirt on vacay or brunch! Pair with the matching top to complete the cute look.

Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

Fit & Features
- Smooth stretchy double-lined knit fabric
- High-rise waist
- Side ruched seams
- Center back slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000021

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Crush Flower Stud Earrings
Major flower power energy happening here. These flower stud earrings add the perfect flirty touch to your everyday vibe—whether it’s jeans and a tee or your fave dress.

Fit & Features
- Dainty metal flower design
- Center rhinestone embellishment
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000122

Category Name: Vacation Looks

Price: $9.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Breezy Fave High Slit Maxi Dress
Show off effortless style in this breezy gauze maxi dress designed with a smocked waist, high front slit, and flowy A-line silhouette. Perf for summer parties, pair with espadrille sandals.

Fit & Features
- Gauze woven fabric, stretchy knit lining
- Sleeveless V-neckline, spaghetti straps
- Open cross-back tie-back design
- Smocked high waist
- Tiered design, thigh-high front slit
- Maxi-length hem, flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000121

Category Name: Vacation Looks

Price: $22.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Breeze Ruffled Eyelet Maxi Skirt
Spring into the new season in this eyelet maxi skirt for vacations or weekend fun! Featuring a flattering high-rise elasticized waist, this skirt will keep you feeling cool and confident. The tiered ruffled silhouette adds a touch of charm, while the maxi-length hem and eyelet lace fabric offer a romantic and airy look. Complete the look with the matching top.

Shop Matching Top: Spring Breeze Sweetheart Tie Eyelet Crop Top

Fit & Features
- Eyelet lace fabric, stretchy shorts lining
- High-rise elasticized waistband
- Tiered ruffled silhouette
- Runs true to size
Style Number/Barcode: 06503-1152

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Time Tropical Floral Mesh Maxi Dress
Get ready to be on island time in this gorg tropical floral mesh maxi dress perf for vacay. Featuring a strapless neckline and high side slit, style with heels.

Fit & Features
- Sheer mesh fabric with full-length knit lining, high stretch
- Large tropical floral print
- Strapless straight neckline
- High-cut side slit
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000102

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunny Posture Tie Back Floral Chiffon Skater Dress
Radiate sunshine energy in this effortless floral chiffon skater dress perfect for graduation, brunch, and any dressy occasion! The sweetheart neckline and adjustable spaghetti straps provide a flattering fit, while the tie-back design adds a unique touch. The skater silhouette and ruffled short-length hem give you a playful look, adorned with a beautiful floral embroidered pattern! Complete the look with simple earrings.

Fit & Features
- Floral embroidered pattern
- Chiffon fabric with woven lining
- Adjustable spaghetti straps, tie-back design
- Sweetheart neckline
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3246

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Love Game Plunge V-Neck Bubble Skater Dress
Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.

Fit & Features
- Poplin woven fabric, sewn-in knit lining
- Plunge V-Neckline
- Short ruffled bubble sleeves
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2935

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dearest Charm Bow Print Skater Dress
Show off your charm in this bow print skater dress boasting flirty details like puff sleeves and a short-length hem perfect for styling with sandals.

Fit & Features
- Bow print, woven fabric, woven lining
- Puff short sleeves
- Square neckline, bust tie
- Stretchy smocked bodice
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3981

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Into Action Floral Skater Dress
Spring into your seasonal closet by adding this floral skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a ruched bust with tie-front detail, and a fit-and-flare silhouette with a short ruffled hem. The dress is composed of chiffon fabric with a stretchy knit lining. Complete the look in trendy wedge sandals and a bracelet.

Fit & Features
- Sleeveless V-neck, adjustable spaghetti straps
- Ruched bust, tie-front detail
- Back zipper and hook-eye closure
- Fit and flare skater silhouette
- Short ruffled hem
- Floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4889

Category Name: Vacation Looks

Price: $5.97 $43.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Eye-Catching Halter Ruffle Chiffon Mini Dress
You'll look positively eye-catching in this floral mini dress at weddings or garden parties! The halter crew neckline and open back ooze elegance, while the ruffled bodycon silhouette flatters your curves. With a mini-length hem, this dress is perfect for any occasion. Complete the look with earrings.

Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Halter crew neckline, spaghetti strap tie
- Open back
- Ruffled bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5627

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wrapped In Power Snake Bracelet
Ssshe’s not your average accessory! This snake wrap bracelet slithers on with attitude—bold, edgy, and ready to strike a statement. Stack it or let it steal the show solo.

Fit & Features
- Smooth, flexible wrap-around design
- Snakehead and tail detailing with engraved texture
- Sculpted metal finish
- Adjustable styling
Style Number/Barcode: 07003-000024

Category Name: Vacation Looks

Price: $7.96 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Set For Good High Rise Texture Mini Skirt
You'll be set for good in this stylish mini skirt all season! Featuring a flattering high rise waist and bodycon silhouette, this mini-length skirt offers the perfect fit. Complete the look with the matching top.

Shop Matching Top: Set For Good Cap Sleeve Slit Texture Crop Top

Fit & Features
- Texture sheer fabric, knit lining, minimal stretch
- High rise waist
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1034

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling The Vibe Rhinestone Star Charm Platform Sneakers
You'll be feeling the vibe of these athleisure sneakers perfect for casual coffee shop runs and errands! These playful kicks feature a round toe, a lace-up placket with a rhinestone star charm, and a comfy footbed with a platform sole and gel insert. Complete the look in a comfy lounge set.

Fit & Features
- Round toe
- Lace-up placket, rhinestone star charm decor
- Chunky platform sole with gel insert
- Comfortable footbed
- Faux leather material
- Runs true to size
Style Number/Barcode: 07407-0227

Category Name: Vacation Looks

Price: $30.90

Availability: Out of Stock
Product Badge:
- Ships Free
Babe In Disguise Square Sunglasses
For when you feel low-key these square sunglasses are perfect for throwing on! They feature a square design, tinted lenses to help protect from the sun, and a comfortable fit. Complete the look with simple earrings.

Fit & Features
- Square design
- Tinted lenses
- Comfortable fit
Style Number/Barcode: 07008-1083

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Picturesque Cutie Lace-Up Floral Bustier
Look and feel cute in this lace-up floral bustier that brings the adorable factor to any outfit!

Fit & Features
- Floral print, eyelet woven-lined fabric
- Sweetheart neckline
- Underwire bust
- Adjustable spaghetti straps
- Lace-up back. flexible boning
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-2776

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Has Sprung Floral Bubble Hem Skater Dress
Let your beauty bloom in this adorable floral skater dress with the sweetest allure. The corset bodice will highlight your waist while the short skater skirt offers the cutest fit-and-flare silhouette.

Fit & Features
- Floral-printed woven fabric with knit lining, minimal stretch
- Sleeveless sweetheart neckline, padded bust with underwire
- Thin tank shoulder straps
- Corset bodice, tie-front detail, high waist seam
- Smocked back design, zipper with hook and eye closure
- Short skater skirt with bubble hem, fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3826

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Social Season Braided Strap Mules
Step into any social event on your calendar in these braided strap platform mules to elevate your look!

Fit & Features
- Block heel
- Square toe
- Braided straps
- Platform sole
- Runs true to size
Style Number/Barcode: 07401-000075

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirt Served Tie-Front Crop Top
Serve flirty without saying a word. This rib knit tie-front top is giving effortlessly hot with a fitted silhouette that’s made for coffee runs, early brunches, and everything in between.

Fit & Features
- Stretchy rib knit fabric
- Short sleeves
- Tie-front design
- Ultra cropped fitted hem
- Runs true to size
Style Number/Barcode: 06202-000022

Category Name: Vacation Looks

Price: $19.90

Availability: In Stock

Available Color: WHITE

Available Size: XS, S, M, L
Weekend Breeze High-Rise Crochet Palazzo Pants
Feel the breeze on the weekend in these crochet palazzo pants at festivals, concerts, or out at the fair! Featuring a high-rise elasticized waistband and a wide-leg silhouette, these pants offer a flattering fit on crochet fabric lined with stretch knit. Complete the look in a crop top.

Fit & Features
- Crochet fabric lined with stretch knit
- High-rise elasticized waistband
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0822

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Style in Check Straw Tote Bag
Always keep your style in check with this checkered straw tote bag, perfect for carrying all of your essentials.

Fit & Features
- Top handles
- Checkered pattern
- Spacious interior
- Straw material
Style Number/Barcode: 07203-000020

Category Name: Vacation Looks

Price: $4.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials