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

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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.

Romantic And Chic Peplum Top
Bring those romantic and chic vibes to your date look with this adorable peplum top. It features adjustable spaghetti straps, a V neckline, a sheer lace top with a lined bust, and a flirty peplum hem. The top is composed of a lightweight gauze and sheer lace fabric with no stretch. Complete your outfit with casual denim for a day date, or a cute mini skirt for a night look.

Fit & Features
- Adjustable spaghetti straps
- V neckline with eyelash lace trim
- Sheer lace top, lined bust
- Back zipper and hook and eye closure
- Mid-length peplum hem
- Gauze and sheer lace fabric
- Runs true to size
Style Number/Barcode: 06003-1244

Category Name: Vacation Looks

Price: $16.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty In Paradise Stud Earrings
Dress like you are on a pretty vacay in paradise with these gorgeous stud earrings. They feature a metal leaf-shaped design with post-back closures. Pair these earrings with a flowy maxi dress and strappy sandals.

Fit & Features
- Metal leaf-shaped design
- Post-back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0780

Category Name: Vacation Looks

Price: $5.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Flair Tassel Earrings
Showcase your bohemian flair with these gorgeous statement earrings. They feature a hammered metal post connected to a half circle-shaped metal detail with a hammered design and fanned out tassels. Pair these on-trend earrings with a flowy mesh duster.

Fit & Features
- Hammered metal post
- Half circle-shaped metal detail with a hammered design
- Fanned out tassels
- Post back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0814

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Tiered Tassel Earrings
Trendy and chic, these statement tassel earrings will elevate your look. They feature a round post connected to four tiers of threaded tassels. Pair these earrings with a casual dress and sandals.

Fit & Features
- Round post
- Four tiered design
- Threaded tassels
- Post back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0815

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ruffled For Florals Midi Dress
Bring the charm with florals and ruffles in this sweet and stunning midi dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back strap design, a chic front slit with flirty ruffle detailing at the hem, and a mid-length, curve-hugging silhouette. The lined scuba knit fabric showcases a gorgeous all-over blooming floral print. Pair this pretty dress with wedges for a head-turning look!

Shop Long Crepe Version: Tiffany Sleeveless High Slit Formal Dress

Shop Crepe Midi Version: Add Some Flair Ruffle Detail Midi Dress

Shop Satin Midi Version: Ravishing Ruffles High Slit Midi Dress

Shop Green Floral Version: Floral Passion Ruffled Midi Dress

Fit & Features
- Sleeveless square neckline, spaghetti straps
- Strapless or adhesive bra recommended
- Cross-back strap design, front slit, ruffled hem
- Mid-length silhouette
- All-over floral print
- Lined scuba knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0513

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
My Own Way High Rise Denim Shorts
Slay in shorts that showcase how unique your style is! The shorts feature a high-rise waist, a single button with hidden zipper closure, light distressing, a Bermuda length with a frayed hem. Complete look with a ruched crop top and t-strap sandals for a casual day out.

Fit & Features
- High rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Light distressing
- Bermuda length with frayed hem
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0186

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High-Rise Frayed Mom Shorts
Take on the day with fab shorts that give those major throwback vibes! The shorts feature a high-rise waist on a trendy mom-leg silhouette, frayed hem with distressed accents, and a slight color fading for the perf vintage vibe. Complete the look with a cute crop top and sneakers.

Fit & Features
- High-rise waist
- Mom style silhouette
- Moderate distressing, frayed hem
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Light wash denim, slight color fade, no stretch
- Runs true to size
Style Number/Barcode: 06603-0174

Category Name: Vacation Looks

Price: $4.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
High Rise Vintage Distressed Denim Shorts
Channel a vintage feel with denim shorts that bring the glam! The shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, moderate distressing, and frayed cutoff hems. Complete look with a crop top and mules.

Fit & Features
- High rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Moderate distressing
- Frayed cutoff hem
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0173

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High-Rise Destructed Cutoff Denim Shorts
These cutoff denim shorts are the must-have pair of the season. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, trendy destructed details, and a frayed, cutoff hem. The dark-wash denim fabric offers a moderate stretch. Complete your look with a graphic tee and sneakers.

Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Destructed details
- Frayed, cutoff hem
- Dark-wash denim fabric
- Moderate stretch
Style Number/Barcode: 06603-0140

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Greek Key Faux Wool Panama Hat
Shade out the haters with a Panama hat that will have you vacay-ready! The hat features a traditional Panama design, a short brim, and Greek key metal chain. The hat is composed of a faux wool material. Complete look with a swimsuit.

Fit & Features
- Panama design
- Short brim
- Greek key metal chain
Style Number/Barcode: 07302-0320

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Passion For Floral Ruched Crop Top
Showcase your passion for florals in this crop top that brings the charm. The crop top features an off-the-shoulder neckline, a bustier-like ruched bodice, padded cups, long sleeves, contrast piping, and a cropped hem. The top is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with high waist jeans and mules.

Fit & Features
- Off-the-shoulder neckline with a sweetheart bust
- Bustier-like ruched bodice
- Padded cups, built-in no-slip strip
- Ruched long sleeves
- Contrast piping, cropped hem
- Floral print
- Lined mesh, form-hugging fit, moderate stretch
Style Number/Barcode: 06001-3035

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chic Babe One-Piece Swimsuit
Showcase your chic style, even as you lounge poolside, in this elevated basic one-piece swimsuit. It features tank-like shoulder straps with tortoiseshell-hued O-ring accents, a scoop neckline, a low scoop back, and a semi-cheeky fit. Pair this swimsuit with a long flowy duster and some trendy sandals.

Fit & Features
- Tank-like shoulder straps
- Tortoiseshell-hued O-ring details
- Scoop neckline
- Low scoop back
- Semi-cheeky fit
- Ribbed fabric
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0220

Category Name: Vacation Looks

Price: $18.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Knot Your Basic Flyaway Tube Top
Giving effortless cool with a twist—literally. With a twist front and flyaway design, this ribbed knit tube top is your not-so-basic basic, perfect for rooftop drinks and summer dates.

Fit & Features
- Ribbed knit fabric, plenty of stretch
- Strapless sweetheart neckline
- Twist-front bust detail
- Front fly-away design
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06005-000040

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: BLUE

Available Size: L
Product Badge:
- Sale
Leopard Print Bikini Top
Keep it fab and fierce in a bikini top that taps into your fashion instincts. The top features a leopard print, molded cups, a small tie-front accent, adjustable spaghetti straps, and a slide-hook closure. Complete your look with the matching bikini top and sunnies.

Shop Matching Bikini Bottoms: Leopard Print Hipster Bikini Bottoms

Fit & Features
- Leopard print
- Molded cups
- Tie front
- Adjustable spaghetti straps
- Slide-hook closure
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0488

Category Name: Vacation Looks

Price: $5.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wrapped In Glam Faux Suede Block Heels
Wrap yourself with luxe heels that elevate your style The heels feature a wrap-around strap design, an open almond toe with a single strap over the toe, and a block heel. The heels are composed of a faux suede material. Complete look with a floral mini dress and handbag.

Fit & Features
- Wrap-around strap design
- Open almond toe
- Single strap over the toe
- Block heel
- Faux suede material
Style Number/Barcode: 07401-2688

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stunning Vibes Backless One-Piece Swimsuit
Showcase chic and stunning vibes as you lounge poolside in this one-piece swimsuit. It features a high neckline, tank shoulder straps that lead to a racerback, a backless design, and a semi-cheeky fit. Pair this swimsuit with a flowy mesh duster and trendy sunnies.

Fit & Features
- High neckline
- Tank shoulder straps
- Racerback
- Open back
- Semi-cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0261

Category Name: Vacation Looks

Price: $13.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fresh Like A Daisy Bikini Top
Keep your look so fab and fresh with a cute bikini top! The bikini top features a plunging scoop neckline with a sexy keyhole, a daisy print, adjustable spaghetti straps, and a slide hook fasten closure. Complete your beachside look with the matching bikini bottoms and sunglasses.

Shop Matching Bikini Bottoms: Fresh Like A Daisy Bikini Bottoms

Fit & Features
- Sleeveless scoop neckline
- Keyhole
- Adjustable spaghetti straps
- Daisy print
- Slide hook fasten closure
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0500

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Butterfly Beauty Baseball Cap
This adorable cap is the perfect addition to your 'fit for those sunny days. It features a traditional baseball cap design with an adjustable back and a front butterfly embroidered design. Complete the look with a crop top and distressed denim shorts.

Fit & Features
- Traditional baseball cap design
- Adjustable back
- Butterfly embroidered design
Style Number/Barcode: 07302-0310

Category Name: Vacation Looks

Price: $7.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendsetting Beauty Two-Pack Necklace Set
Showcase your chic style like the trendsetting beauty you are by accessorizing with this necklace set! It features two necklaces, one with two shorter dainty chains with small stone charms and a center crescent moon charm embellished with mini cubic zirconia stones. The longer necklace has a shorter layer with a center crescent moon charm and a longer layer with a textured dainty chain and a center lariat with a vertical bar accent. Layer these necklaces over a graphic tee for a cool vibe.

Fit & Features
- Two-pack necklace set
- Dainty chains
- Crescent moon charms
- Cubic zirconia embellishments
- Lariat design with a vertical bar charm
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0655

Category Name: Vacation Looks

Price: $7.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Double O-Ring Buckle Belt
Elevate your basic outfit and give it a trendy vibe with this chic faux leather belt. It features a metal double O-ring buckle. Pair this belt with your fave pair of denim and strappy heels.

Fit & Features
- Faux leather belt
- Metal double O-ring buckle
Style Number/Barcode: 07301-0229

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Flirt Floral Crochet Bralette
Showcase your effortless beauty in this flirty bralette! It features dual adjustable spaghetti straps that lead to a cross back design, a deep V neckline with a lined bust, sheer floral crochet fabric, a sheer and stretchy smocked back, and a cropped, form-hugging fit. Pair this bralette with a pair of high-rise denim shorts and strappy sandals.

Fit & Features
- Dual adjustable spaghetti straps
- Cross back design
- V neckline with a lined bust
- Sheer floral crochet fabric
- Sheer and stretchy smocked back
- Cropped, form-fitting style
Style Number/Barcode: 07107-0572

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Glam Ribbed Bikini Top
Channel a glam vibe with a bikini top that is so vacay-ready! The bikini top features a wired V-neckline, ribbed detail, adjustable spaghetti straps, and a tie-back accent. Complete look with the matching bikini bottoms and sandals.

Shop Matching Bikini Bottoms: Basic Glam Ribbed Hipster Bikini Bottoms

Fit & Features
- Sleeveless wired V-neckline
- Ribbed detail
- Adjustable spaghetti straps
- Tie back accent
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0498

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Clearly On-Trend Denim Lucite Heels
Step up your style with these trendy lucite heels! They feature an open almond toe, a clear toe strap, an adjustable clear ankle strap, an open back, a denim sole, and a lucite heel with denim detail. Pair these chic shoes with a graphic tee and black skinny jeans.

Fit & Features
- Open almond toe with a toe strap
- Adjustable ankle strap
- Open back
- Denim sole
- Lucite heel with denim detail
- Clear PVC straps
- Runs true to size
Style Number/Barcode: 07401-2698

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Good Vibes Tank Swim Top
You're all about those good vibes this year! Showcase your trendy style in this elevated basic swim top. It features adjustable tank-like shoulder straps, a notched V wired front, and a tie back closure. Complete your look with the matching swim bottoms and some cute sandals.

Shop Matching Swim Bottoms: Good Vibes Hipster Swim Bottoms

Fit & Features
- Adjustable tank-like shoulder straps
- Notched V wired front
- Tie back closure
- Ribbed fabric
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0499

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials