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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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.

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
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
Worth It Linen Wide-Leg Pants
These linen pants are worth taking on your next weekend adventure! They feature a high-rise waist, back zipper closure, side pockets, and a wide-leg silhouette. Complete the look with the matching top.

Shop Matching Top: Worth It Linen Tube Top

Fit & Features
- High-rise waist
- Back zipper closure
- Side pockets
- Wide-leg silhouette
- Linen fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06302-0726

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Worth It Linen Tube Top
This linen-blend tube top is worth taking on your next weekend adventure! It features a sleeveless bodice, a convertible design so you can style it multiple ways, and a cropped hem. Complete the look with the matching bottoms.

Shop Matching Bottoms: Worth It Linen Wide-Leg Pants

Fit & Features
- Sleeveless bodice
- Convertible design
- Multiple ways to style
- Cropped hem
- Linen-blend fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06003-2167

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Remy High-Rise Destructed Frayed Shorts by Windsor Denim
Take your everyday 'fit up a notch with the Remy destructed frayed shorts by Windsor Denim. They feature a high-rise waist, on-trend destructed detailing, and a majorly frayed cut-off hem. The light-wash denim fabric has a rigid fit with no stretch. Style with a graphic tee and sneakers.

Fit & Features
- High-rise waist
- Destructed accents
- Frayed cut-off hem
- Front button-down closure
- Five-pocket and belt loop design
- Light wash denim fabric, rigid fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0247

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Retro Upgrade Sleek Rectangle Sunglasses
Upgrade your look with these retro-cool sunglasses featuring sleek rectangular tinted lenses and clear plastic arms. Style with a casual mini dress for a pool party!

Fit & Features
- Sleek rectangular tinted lenses
- Clear plastic arms
- 100% UV protection
Style Number/Barcode: 07008-0999

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Outer Limits Silver Racer Sunglasses
Your style will look out of this world in these retro-fab silver sunglasses featuring a geometric style plastic frame, tinted lenses, and a sleek design. Complete the look in lug booties.

Fit & Features
- Silver geometric style plastic frame
- Sleek design
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0997

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Attitude Round Metal Frame Sunglasses
Serve major attitude in these on-trend round sunglasses featuring a sleek metal frame, brown tinted lenses, rubber nose, and arm supports. Complete the look in sassy sandals for a day out with friends!

Fit & Features
- Sleek metal round frame
- Brown tinted lenses
- Rubber nose and arm supports
- 100% UV protection
Style Number/Barcode: 07008-1001

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Strides Chain-Detail Jelly Sandals
Make trendy strides in these of-the-moment jelly sandals. They feature a square toe, a dual strap design with chunky chain-link accents, an open back for easy on-and-off styling, and a flat sole. Style with a casual dress and a mini handbag.

Fit & Features
- Square-shaped toe
- Dual strap design
- Chunky chain-link accents
- Open back
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-1130

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Can't Help It Jelly Bejeweled Flat Sandals
You can't help but flaunt your glam in these clear jelly sandals featuring a square toe, a wide strap with statement rhinestone jewels, and a flat sole. Style with a chic handbag for a daytime soiree!

Fit & Features
- Square toe
- Wide strap
- Rhinestone jewels
- Flat sole
- Clear jelly material
- Runs true to size
Style Number/Barcode: 07404-1128

Category Name: Vacation Looks

Price: $5.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Little Princess Jeweled Thong Sandals
Grace everyone with your princess energy in these stunning thong sandals to bring the glamour to sitting poolside in a private cabana with the girls! They feature a square toe, colored gemstones with rhinestone trim on thin PVC clear straps, a flat sole, a metallic footbed, and a colored rhinestone ankle chain strap with a lobster clasp closure. Complete the look in a chic duster kimono to layer over your swimsuit!

Fit & Features
- Square toe
- Colored gemstones, rhinestone trim
- PVC clear thong straps
- Flat sole, metallic footbed
- Colored rhinestone ankle chain strap
- Lobster clasp closure
- Runs true to size
Style Number/Barcode: 07404-1138

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreamy In Floral Satin Midi Dress
Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.

Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Curve-hugging, slim silhouette
- Side slit accent
- Midi-length hem
- Floral print, silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4985

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Favorite Pick Ruched Slit Midi Dress
Your new favorite midi dress for looking stylish and cute! It features a sleeveless square neck, sleek bungee spaghetti straps, a bodycon silhouette, and a side slit with a ruched drawstring that lets you customize the fit. The midi dress is composed of a rib-knit fabric with lining and plenty of stretch. Complete the look in trendy flat sandals for a bridal shower or brunch!

Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Bodycon silhouette
- Side slit, ruched adjustable drawstring
- Midi-length hem
- Rib knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5034

Category Name: Vacation Looks

Price: $5.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Dreamer Sweater Knit Halter Top
Create a dreamy bohemian-inspired look with this sweater knit crop top. It features a sleeveless halter neckline with spaghetti straps, an open back with cross-back straps and a lower lace-up strappy design, and a fitted, cropped hem with a dainty eyelet pattern. Style with a printed maxi skirt and strappy sandals.

Fit & Features
- Sleeveless halter neckline
- Spaghetti straps
- Open back, cross-back straps
- Lower lace-up strappy design, tie closure
- Fitted, cropped hem, eyelet pattern
- Ribbed sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1445

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Girl Era Chunky Platform Mules
You'll be in your trendy girl era with these fabulous chunky platform mules! They feature an open almond-shaped toe, a wide banded toe strap, an open back for easy on-and-off styling, a chunky platform with a lug sole, and a tall block heel. Style with a flirty floral dress.

Fit & Features
- Open almond-shaped toe
- Wide banded toe strap
- Open back
- Chunky platform, lug sole
- Tall block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4200

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Total Glam Vibe Rhinestone Lace-Up Sandals
Give off a total glam vibe in these rhinestone lace-up sandals that will add a trendy sparkle! They feature an almond-shaped toe with a strap, an asymmetric strappy design that laces up the leg with mini rhinestone embellishments, and a comfortable flat sole. Style with a graphic tee and distressed denim shorts for an edgy look.

Fit & Features
- Almond-shaped toe, toe strap
- Asymmetric strappy lace-up design, tie closure
- Mini rhinestones
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1135

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Country Style Western Denim Booties
Amp up your looks for festival season or every day with this trendy pair of western denim booties! They feature a mid-calf height with loops on each side for easy on-and-off styling, an inner zipper closure, a pointed toe, a comfortable stacked block heel, and cute western-inspired stitching with a side pocket detail. Style with a casual dress and hoop earrings!

Fit & Features
- Mid-calf height
- Loop accents, inner zipper closure
- Pointed toe
- Stacked block heel
- Denim fabric
- Western-inspired stitching, side pocket detail
- Runs true to size
Style Number/Barcode: 07403-1636

Category Name: Vacation Looks

Price: $18.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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