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.

Wing It Butterfly Charm Anklet
Wing your look in this stylish butterfly charm anklet featuring a dainty chain, rhinestone drops, and an adjustable lobster clasp closure. Complete the look in a cute bikini set and cover-up.

Fit & Features
- Butterfly charms
- Rhinestone drops
- Dainty chain
- Adjustable lobster clasp closure
Style Number/Barcode: 07003-0341

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Playful Cutie Straw Floppy Hat
Show off your playful side in this straw floppy hat featuring an oversized design and a ribbon trim. Complete the look in a cute sundress for a day spent in the sun.

Fit & Features
- Oversized design
- Floppy brim
- Ribbon trim
- Straw material
Style Number/Barcode: 07302-0498

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Saddle Up Straw Cowboy Hat
Back in the saddle again looking so country-chic! This straw cowboy hat is the perfect finishing touch to your music festival outfit. It features a classic curved brim and a unique beaded string with a knot-tie accent.

Fit & Features
- Curved brim
- Beaded string, knot-tie accent
- Adjustable interior string with bead
- Straw material
Style Number/Barcode: 07302-0587

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Babe Tie-Dye Mini Skirt
You're a total bold babe when it comes to your style, so this mini skirt was made for you. It features a high-rise waist, side ruched detailing leading to an adjustable drawstring at the hem, a short, curve-hugging fit, and a trendy all-over tie-dye print. Style with the matching crop top and statement earrings.

Shop Matching Top: Bold Babe Tie-Dye Crop Top

Fit & Features
- High-rise waist
- Side ruching, adjustable drawstring at the hem
- Mini-length, form-fitting silhouette
- Tie-dye print
- Soft brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0599

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vintage-Chic Oval Sunglasses
Accessorize your summer looks with these vintage-chic shades! The sunglasses feature oval-shaped tinted lenses with a tortoise-shell plastic frame. Style with a trendy shoulder bag.

Fit & Features
- Oval-shaped tinted lenses
- Tortoise-shell plastic frame
Style Number/Barcode: 07008-0961

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Talks Strappy Bikini Top
Sit pretty poolside in this sultry bikini top! It features a sleeveless tank-style bodice with a plunge v-neckline with a strappy design, removable padding, and a hook-back closure. Composed of a sleek-lined knit fabric. Style with matching bottoms and oversized sunnies.

Shop The Matching Bottoms: Sultry Talks Hipster Bikini Bottoms

Fit & Features
- Sleeveless tank style straps
- Plunge v-neckline with a strappy design
- Removable padding for support and shaping
- Hook-back closure
- Sleek knit lined fabric
- Fits true to size
Style Number/Barcode: 07104-0608

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All This Love Cowl Halter Crop Top
A sweet crop top with a sultry open back and cowl halter neckline that dresses up your favorite jeans.

Fit & Features
- Smooth knit stretchy fabric
- Cowl halter neckline, spaghetti strap tie
- Open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000087

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Babe Tie-Dye Crop Top
You're a total bold babe when it comes to your style, so this crop top was made for you. It features a sleeveless halter neckline with spaghetti straps and a center O-ring accent, an alluring center cutout at the bust, a cropped, form-hugging fit, and a trendy all-over tie-dye print. Style with the matching mini skirt and statement earrings.

Shop Matching Bottoms: Bold Babe Tie-Dye Mini Skirt

Fit & Features
- Sleeveless halter neckline, front O-ring accent
- Spaghetti straps, tie at the back of the neck
- Center cutout at the bust
- Cropped, form-hugging fit
- Tie-dye print
- Soft brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4010

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fun In Fringe Mesh Swim Wrap
Have fun in the sun looking stylish in this fringe mesh swim wrap! It features a side-tie knot closure, sheer design, and fringe trimming. Complete your vacay look in a fab bikini set.

Fit & Features
- Side-tie knot closure
- Sheer mesh design
- Fringe trimming
- Moderate stretch
Style Number/Barcode: 07305-0383

Category Name: Vacation Looks

Price: $1.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Do It Like Bey Layered Belly Chain
Showcase your inner diva at the pool party in this layered belly chain featuring three snake chains and a lobster clasp closure. Complete the look in a sultry bikini set for a pool party.

Fit & Features
- Layered design
- Three snake chains
- Lobster clasp closure
Style Number/Barcode: 07301-0444

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Shady Square Oversized Sunglasses
Shade your eyes from the sun's rays in these oversized sunglasses featuring square plastic frames, tortoise patterns, and gradient lenses. Complete the look in a chic jumpsuit for wine tasting.

Fit & Features
- Square plastic frames
- Oversized design
- Tortoise pattern
- Gradient lens
Style Number/Barcode: 07008-0962

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bring That Glow Swim Top
Bring that glow to your poolside look with this bright swim top that will have all eyes on you! It features a convertible bandeau fit with spaghetti straps you can tie in a halter style, a cross-front design, as a one-shoulder neckline, or as a cute bralette. Style with the matching swim bottoms and some sleek shades.

Shop Matching Bottoms: Bring That Glow Swim Bottoms

Fit & Features
- Convertible bandeau fit
- Spaghetti straps
- No padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0682

Category Name: Vacation Looks

Price: $4.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Silhouette One-Piece Swimsuit
Showcase a sultry silhouette in this chic one-piece! The swimsuit features a plunging V-neck and back, tank shoulder straps, a padded bust, sheer mesh inserts at the seams, a high waist design, and a semi-cheeky fit. Style with a flowy kimono and strappy sandals.

Fit & Features
- Deep V-neck and back
- Tank shoulder straps
- Removable padding
- Sheer mesh inserts, nude hue
- High waist design, semi-cheeky fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0297

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Mermaid Vibes Bikini Top
Bring gorgeous mermaid vibes to your poolside look with this alluring bikini top. It features a V-wired bust, adjustable spaghetti straps for a customized fit, and an all-over metallic fishnet design. Style with the matching bikini bottoms.

Shop Matching Bottoms: Major Mermaid Vibes Bikini Bottoms

Fit & Features
- V-wired bust, no padding
- Adjustable spaghetti straps
- Back strap, slide-hook closure
- Metallic fishnet design, full lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0633

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Secret Garden Chiffon Flowy Shorts
This floral chiffon top is perfect for a garden party! Featuring long peasant sleeves, a surplice v-neckline, back smocked panel, and a cropped hem. Complete the look in the matching top.

Shop Matching Top: Secret Garden Chiffon Surplice Top

Fit & Features
- High-rise waist
- Back zipper, hook and eye closure
- Flowy silhouette
- Floral pattern
- Chiffon-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06403-0216

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Simple Chic Vibe Swim Tank
Simple yet so chic, this swim tank will elevate your poolside look. It features a scoop neckline, an alluring center cutout at the bust with dual tortoise-shell O-ring accents, thin tank shoulder straps, and a back bar strap design. Style with the matching swim bottoms.

Shop Matching Bottoms: Simple Chic Vibe Swim Bottoms

Fit & Features
- Scoop neckline
- Removable padding
- Center cutout, dual tortoise-shell O-rings
- Tank shoulder straps
- Back bar strap detailing
- Ribbed fabric, moderate stretch
- Runs small, size up one size
Style Number/Barcode: 07104-0609

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wrapped In Sultry Style Cover-Up
Wrap yourself in chic and sultry style with this alluring fishnet cover-up. The swim wrap features an asymmetrical curve-hugging silhouette you can tie at the waist. Layer this wrap over your fave bikini with strappy sandals.

Fit & Features
- Asymmetrical form-fitting silhouette
- Tie-waist detail
- Sheer fishnet material
- Minimal stretch
Style Number/Barcode: 07305-0385

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spiraling Chic Metal Arm Cuff
This chic spiral arm cuff will add the perfect touch to your night look! Perfect for styling with a sleek satin long dress for a dressy dinner party.

Fit & Features
- Spiral metal design
- Stretches-to-fit
Style Number/Barcode: 07003-0349

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Ready Printed Tie-Front Top
Look like you're ready to jet set off on an island getaway in this printed top! It features short flutter sleeves, a V-neckline, a tie-front design, and a cropped fit. The all-over palm leaf print brings those vacay vibes. Style with the matching mini skirt!

Shop Matching Bottoms: Island-Ready Printed Mini Skirt

Fit & Features
- Short flutter sleeves
- V-neckline
- Tie-front
- Cropped, form-hugging fit
- Palm leaf print
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0305

Category Name: Vacation Looks

Price: $9.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island-Ready Printed Mini Skirt
Look like you're ready to jet set off on an island getaway in this printed mini skirt! It features a high-rise waist, a short, curve-hugging silhouette, and a chic front dual slit design. The all-over palm leaf print brings those vacay vibes. Style with the matching crop top!

Shop Matching Top: Island Ready Printed Tie-Front Top

Fit & Features
- High-rise banded waist
- Mini-length, form-fitting silhouette
- Front dual slit design
- Palm leaf print
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0634

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Breezy Boho Sheer Lace Asymmetric Maxi Skirt
Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties.

Fit & Features
- Sheer lace fabric with mini-length knit lining, plenty of stretch
- High-rise waist
- Ruching, adjustable drawstring
- High side slit
- Asymmetric maxi-length hem
- Flowy fit
- Runs true to size
Style Number/Barcode: 06501-1065

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Reese Extra High Waist Cutoff Denim Shorts by Windsor Denim
Create a bold moment in the Reese denim shorts by Windsor Denim. The jean shorts feature a flattering, extra high rise waist, distressed accents, and an edgy cut-off frayed hem on a medium wash vintage-inspired denim fabric with a color fade effect. Complete the look in a cute backless bodysuit and sandals for a summer vibe.

Fit & Features
- Flattering, extra high rise waist
- Distressed accents, cutoff frayed hem
- Form-fitting design
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash non-stretch denim, color fade effect
- Fits true to size
Style Number/Barcode: 06603-0235

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Out Sailing Satin Tie-Front Top
This sleek satin tie-front top is perfect for a day on the water! It features flowy half-length kimono-style sleeves, a V-neckline, a chic tie-front design, and a relaxed, cropped fit. The all-over palm leaf print will really bring those vacay vibes. Style with high waist linen pants and strappy sandals.

Fit & Features
- Half-length kimono-style sleeves
- V-neckline
- Tie-front
- Relaxed fit, cropped silhouette
- Palm leaf print
- Satin woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1321

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Bell Tie-Front Top
Effortless and trendy, this boho-inspired woven top features flowy kimono sleeves, a plunge V-neckline, and a flirty tie-front hem. Complete the look in a panama hat for a cool desert trip.

Fit & Features
- Kimono sleeves
- Plunge V-neckline
- Tie-front hem
- Woven gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1186

Category Name: Vacation Looks

Price: $9.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

HomeVacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials