Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.

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STYLE SPOTLIGHT

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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.

Trendy Deets Stud And Hoop Earrings Set
You'll obsess over the trendy deets of this stud and hoop earrings set! The multi-pack features six pairs of varying earrings, including circular studs, rhinestone studs, sleek bar studs, classic huggie hoops, bar studs with hanging chain design, and chic cross-front rhinestone hoops. Include post-back closures. Style with a layered charm necklace.

Fit & Features
- Six-pack earrings set
- Circular studs, rhinestone studs, bar studs
- Huggie hoops
- Bar studs with hanging chain detail
- Cross-front rhinestone hoops
- Omega closure, post-back closures, rubber stoppers
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1974

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Mood Floral Crochet Sandals
These floral crochet sandals will put you in the mood for cute summer styling! Designed with a synthetic faux leather upper, they feature an open round toe, a wide banded strap with an adorable floral crochet design in bright hues, and a flat sole. The open back offers effortless on-and-off styling. Pair these sandals with a charm necklace and aviator sunglasses!

Fit & Features
- Synthetic faux leather upper
- Open round toe
- Single banded strap
- Multi-colored floral crochet design
- Open back, flat sole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1184

Category Name: Vacation Looks

Price: $20.90

Availability: Out of Stock
Product Badge:
- Ships Free
Ocean Eyes Halter Maxi Dress
Serving sultry mermaid vibes, this maxi dress is pure liquid allure. With its daring plunge, bold hardware detail, and sleek fit, it’s the statement dress that makes every entrance unforgettable.

Fit & Features
- Abstract tie-dye print, mesh-lined stretchy fabric
- Plunge halter cowl neckline with hardware insert
- Open back with tie closure
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000674

Category Name: Vacation Looks

Price: $49.90

Availability: In Stock

Available Color: BLUE

Available Size: XS, S, M, L
Rodeo Aesthetic Western Concho Belt
Cinch together your western look with this concho belt featuring square shapes with colored stones on a chain with a secure lobster clasp closure. Perfect for styling with cowboy boots.

Fit & Features
- Square shapes with colored stones
- Chain
- Lobster clasp closure
Style Number/Barcode: 07301-0674

Category Name: Vacation Looks

Price: $2.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In Full Faith Cross Rhinestone Charm Belly Chain
Perfect for accentuating your waist, this belly chain complements both casual and dressy outfits with subtle shine and meaningful detail. This delicate belly chain features a sparkling cross charm adorned with rhinestones, adding a touch of elegance and faith-inspired beauty to your look.

Fit & Features
- Cross charm
- Rhinestone charm
- Layered chain design
- Lobster clasp closure
Style Number/Barcode: 07002-000020

Category Name: Vacation Looks

Price: $12.90

Availability: Out of Stock
Product Badge:
- Ships Free
Style On Point Cat-Eye Sunglasses
These cat-eye sunglasses are here to make sure your style is always on point! They feature tinted lenses and a comfortable fit. Complete the look with a denim jacket and sandals!

Fit & Features
- Cat-eye silhouette
- Tinted lenses
- Comfortable fit
Style Number/Barcode: 07008-1086

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cool Living Aviator Sunglasses
A pair of cool aviator sunglasses featuring a sleek metal frame, smokey tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.

Fit & Features
- Sleek metal frame
- Smokey tinted lenses
- 100% UV protection
- Rubber nose supports
Style Number/Barcode: 07008-1103

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Western Life Colored Stone Concho Chain Belt
A statement concho chain belt features textured squares with colored stones and an adjustable lobster clasp closure. Style with a denim short dress and boots.

Fit & Features
- Textured squares with colored stones
- Adjustable lobster clasp closure
Style Number/Barcode: 07301-1192

Category Name: Vacation Looks

Price: $2.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunset Drinks Platform Block Heels
These fab platform block heels were made to be worn while sipping on some drinks at sunset! They feature an open almond-shaped toe with an adorable knotted toe strap design, a thin adjustable ankle strap with a buckle closure, a closed back, a tall platform sole, and a chunky block heel. Style with your fave summer dress for happy hour!

Fit & Features
- 5" Block heel
- Open almond toe, knotted toe strap design
- Adjustable ankle strap with buckle closure, closed back
- Platform sole, padded faux leather insole
- Natural heels are woven material with a metallic threaded design
- Denim heels are denim material
- Runs true to size
Style Number/Barcode: 07401-4857

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Heat Wave V-Cut Bikini Bottoms
Bring the heat to your summer vacay in these bikini bottoms featuring a high V-cut waist and cheeky fit. Pair with the matching bikini top.

Shop Matching Top: Heat Wave Halter Bandeau Bikini Top

Fit & Features
- Nylon-blend fabric, high stretch
- High V-cut waist
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000007

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charmed Strapless Ruffled Woven Skater Romper
They'll be oh-so-charmed by you in this flirty ruffled woven skater romper! Designed with a breezy woven fabric, it features a strapless straight-across neckline, flexible boning at the bodice for added structure, a tie-back design for a stylishly cinched waist, an adorable short ruffled overlay over flowy shorts, and a fit-and-flare silhouette. Complete your look with hoop earrings and sneakers for a cute and casual vibe.

Fit & Features
- Woven fabric, stretchy knit lining
- Strapless straight neckline, flexible boning
- Tie-back design
- Back zipper with hook-eye closure
- Ruffled overlay, flowy shorts
- Fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 06403-0400

Category Name: Vacation Looks

Price: $20.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Painted Muse Tube Slit Maxi Dress
Like wearing a work of art, this strapless maxi dress stuns with a marbled print and a curve-hugging silhouette. The sleek side slit adds just the right touch of drama for gallery nights, rooftop hotel bars, or dinner downtown.

Fit & Features
- Marbled print stretchy mesh fabric, sewn-in lining
- Tube strapless neckline
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000247

Category Name: Vacation Looks

Price: $42.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L, XL
Gleam Always Snake Chain Necklace
Always gleam in this essential snake chain necklace to give every outfit the perfect accessory! Complete the look in a bodycon dress for any occasion.

Fit & Features
- Snake chain
- Back adjustable chain with clasp closure
Style Number/Barcode: 07002-1817

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Catch Tie Front Knit Bandeau
Catch this stylish bandeau top for the ultimate vacation look! Featuring a strapless sweetheart neckline and a tie-front bust for a flirty allure while the ultra-cropped hem adds a trendy touch. Complete the look with the matching skirt.

Shop Matching Bottoms: Stylish Catch High Rise Slit Midi Skirt

Fit & Features
- Knit fabric, sewn-in knit lining, minimal stretch
- Strapless sweetheart neckline
- Tie-front bust
- Ultra-cropped length
- Runs true to size
Style Number/Barcode: 06003-2418

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Adventure Strapless Paisley Satin Crop Top
Endless summer adventures call for this trendy paisley satin crop top! Featuring a flattering strapless neckline, a stretchy smocked bandeau lining, and a tie-back closure for the perfect fit. Complete the look in denim shorts and sunglasses!

Fit & Features
- Paisley print, non-stretch satin fabric
- Strapless neckline
- Tie back design
- Stretchy smocked bandeau lining
- Pointed crop hem
- Runs true to size
Style Number/Barcode: 06003-2544

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Social Butterfly Flower Hoop Earrings Set
The perfect three-pack earring set to adorn all of your outfits for everything on the calendar! This set has one pair of rhinestone embellished butterflies, one pair of flowers, and one pair of rhinestone trim hoop earrings each with post-back closures. Complete the look with dressy heels.

Fit & Features
- Thre-pack earrings set
- One pair of rhinestone butterflies
- One paid of flowers
- One pair of rhinestone trim hoop earrings
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2032

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Loving Heart Shell Necklace
Fall for this heart shell necklace to adorn your vacation or weekend outfit! Complete the look in cute sandals.

Fit & Features
- Heart shell charm
- Cord strand
- Lobster clasp closure
Style Number/Barcode: 07002-1838

Category Name: Vacation Looks

Price: $2.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep It Chic Doorknocker Hoop Earrings
Keep your everyday 'fits chic and on-trend with these sleek doorknocker hoop earrings! They feature a large teardrop-shaped post with a hanging hoop design. Include a post-back closure. Complete the look with a ring set.

Fit & Features
- Large teardrop post
- Hanging hoop design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1986

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Season Staple Denim Print Faux Leather Shoulder Bag
Trendy with a chic structure, this denim print faux leather shoulder bag is a staple for the season. Designed with a medium-wash denim print on smooth faux leather material, this bag is a fabulous must-have! It features a small half-moon shape with curved seam accents, a snap button closure with a buckle strap accent, a top zipper closure to secure your essentials in the spacious woven interior, and an adjustable shoulder strap. Pair with the matching heels for a seamlessly stylish 'fit!

Shop Matching Heels: Season Staple Denim Print Faux Leather Stiletto Heels

Fit & Features
- Faux leather material with medium-wash denim print
- Small half-moon design
- Snap button closure with buckle strap accent
- Top zipper closure
- Woven interior with pouch and zippered pocket
- Adjustable shoulder strap
- Black is solid faux leather material
Style Number/Barcode: 07203-2018

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachy Blossom Three-Pack Hair Clip Set
Bring the vacay vibes to your hair. This three-pack of tropical flower claw clips is perfect for adding a playful pop to messy buns, beach waves, or any carefree vacay style.

Fit & Features
- Three-pack hair clip set
- Tropical flower design
- Claw clip closure
Style Number/Barcode: 07006-000065

Category Name: Vacation Looks

Price: $12.90

Availability: In Stock

Available Color: MULTI

Available Size: NS
Whimsical Chic Organza Butterfly Statement Earrings
Create an enchanting spring or summer party look with these whimsical butterfly statement earrings! They feature a gorgeous long cascading design with a dainty chain, large and small sheer organza butterfly accents, and a sparkling round rhinestone detail at the end. Include a fish hook closure. Style with a ring set.

Fit & Features
- Long linear design
- Dainty chain
- Sheer organza butterfly accents
- Round rhinestone detail
- Fish hook closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1991

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Flair Oversized Square Sunglasses
Add that chic flair to your everyday looks with these sleek square sunglasses! They feature an oversized square-shaped design, a trendy tortoiseshell plastic frame and arms, built-in nose pads for support, and tinted lenses. Style these shades with a faux leather handbag.

Fit & Features
- Oversized square-shaped design
- Tortoiseshell plastic frame and arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1072

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fab Trendsetter Rectangle Sunglasses
Top off your fab summer 'fits with these trendy shades! The sunglasses feature a rectangular-shaped design, a plastic frame with a glam metallic sheen, built-in nose pads, and tinted lenses. Style with hoop earrings and a charm necklace.

Fit & Features
- Rectangular-shaped design
- Plastic frame, metallic sheen
- Built-in nose pads
- Tinted lenses
Style Number/Barcode: 07008-1090

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Glow Tube Floral Mini Dress
Sun, skin, and this dress—name a hotter trio. With bold blooms and a sleek bodycon fit, this strapless mini is your go-to for nights out or island dreams.

Fit & Features
- Floral print, knit fabric, moderate stretch
- Tube strapless neckline
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000194

Category Name: Vacation Looks

Price: $9.97 $35.90

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