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.

Romantic Blooms Floral Chiffon Wrap Mini Dress
Cupid's got us struck! This romantic airy mini dress is perf for that daytime date you got lined up! Add block heels and a cute cross-body and you'll be all set bb!

Fits & Features
- Sheer Short Sleeves & Back
- Plunging V Neckline
- Tie Waist Wrap Design
- Mini Length Silhouette
- Chiffon Fabric I Fully Lined I Floral Print
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05101-0796

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Thing Chiffon Wrap Mini Dress
Charm them all, sweet thangggg! They'll be enamored by you in this cute mini dress! Dress up by wearing block heels and adding a cute mini purse!

Fits & Features
- Sheer Flutter Sleeves & Back
- Plunging V Neckline
- Tie Waist Wrap Design I Belt Loops At Back
- Mini Length I Overlap Ruffle-Trim Hem
- Chiffon Fabric I Lined
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05101-0798

Category Name: Vacation Looks

Price: $17.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Summer Mood Wooden Beaded Mini Tote
Get in that sunny day state of mind! We are looking forward to a little vacation time, and this will be our go-to resort wear baybay! The neutral tones pair well with all 'fits but we especially love this beaded beauty styled with a fresh linen two piece!
- Long square shape
- Handle cut out
- Wooden beaded design
- Unlined
Style Number/Barcode: 07203-0288

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
By The Ocean Shell Drop Earrings
Perfect for vacation, we can already picture it! Style with waved hair, and a flowy white dress!
- Post with drop shell design
- Gold textured finish
- Post back closure
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0442

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Down To The Last Detail Wooden Beaded Purse
Get those sunny day vibes down to the last detail! Switching out your everyday purse for something with a little color and texture makes all the difference, especially on vacay!
- Medium sized
- Unlined
- Double handles
- Tightly woven wooden beading
- Multi-toned
Style Number/Barcode: 07203-0220

Category Name: Vacation Looks

Price: $14.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hello Summer Woven Straw Tote Bag
Hello summer, it has been way too long! Time to sit back and relax with the essentials by your side. Perfect for vacay or a day at the beach!
- Large circular design
- Faux leather handles
- Woven straw
- Embroidered "Hello Summer" script
Style Number/Barcode: 07203-0252

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ruffle Detail Eyelet Off The Shoulder Mini Dress
Ruffle up your gorg look with this effortless eyelet detail mini dress! Pair with some gold hoops and strappy mules for an everyday style you'll love!

Fit & Features
- Off the shoulder square neckline
- Short ruffle sleeves
- Ruffle overlay
- Center ruffle detail
- High waist
- Short ruffle hem
- Eyelet detail woven fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0764

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Dreamy In Florals Tie Front Mini Dress
Bring the spring vibes in this cute and dreamy mini dress! We'd love to see you styling this with a pair of white sneakers or chunky heels!

Fits & Features
- Spaghetti Straps
- Plunging V Neckline I Bust Tie With Keyhole Opening I Square Back
- Mini Length Silhouette
- Textured Knit Fabric I Ditsy Floral Print
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05101-0442

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunset Happy Hour Ruffled Skater Dress
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.

Fit & Features
- Sleeveless V-neckline
- Halter tie-back straps, open back
- Stretchy smocked high waist
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Twill fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-5531

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ruched And Ruffled Mini Dress
This ruched and ruffled LBD will become your new fave dress to hit the town in with your girls! Pair with some strappy heels and layer on a chic faux leather jacket for a fab look!

Fit & Features
- Spaghetti straps
- Slight sweetheart neckline
- High waist
- All over ruched detailing
- Drawstring at hem | Ruffle hem
- Knit fabric | Knit lining
- Form hugging fit | Moderate stretch
Style Number/Barcode: 05101-0777

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stunning Leaf Duster Earrings
Showcase stunning looks in these boho chic leaf duster earrings!
- Fish hook closure
- Textured leaf duster design
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0413

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Not The Drama Crop Top
Keep it fab without the drama in this cute crop! Pair it with high waist pants and a pop of floral print for a head-turning look!

Fit & Features
- V-Neckline
- Adjustable Spaghetti Straps
- Lined Embroidered Bodice
- Sheer Unlined Smocked Back
- Cropped Hem
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 06003-0960

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lace It Up Denim Catsuit
Lace-up a fab look in this must-have denim catsuit! Pair this beauty with pumps and layers of dainty pieces to create a look that is ready to slay bby!

Fit & Features
- V-Neckline | Spaghetti Straps
- Open Back
- Lattice Back Straps
- Back Pockets
- Straight Leg Fit | Raw Edge Hem
- Denim Fabric
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 06602-0145

Category Name: Vacation Looks

Price: $6.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Speechless Strapless Floral Ruffle Mini Dress
Leave everyone speechless when you stroll in wearing this floral mini dress at parties or brunch! The strapless neckline and stretchy smocked bodice provide a comfortable and flattering fit, while the dainty floral print and embroidery add a touch of whimsy. Complete the look with sunnies.

Fit & Features
- Dainty floral print and embroidery
- Woven fabric, some stretch
- Fitted silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5456

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep It Boho Chic Kimono
It's festival season bby! Layer this sheer crochet lace kimono over your 'fit for a boho chic vibe!

Fit & Features
- Short billowy kimono style sleeves
- Drape open front
- Flowy, comfortable fit
- Sheer mesh fabric
- Crochet lace trim details
- Moderate stretch
Style Number/Barcode: 06204-0346

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Best Life Culotte Pants
Live your best life in these effortlessly chic pants! Pair them with a sassy graphic tee and strappy sandals for a season-ready look!

Fit & Features
- High Rise Waist
- Tie Waist Belt
- Single Button and Zipper Closure
- Slant Pockets
- Straight Culotte Leg
- Lined Linen Knit Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 06302-0152

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Vacation Long Platform Espadrilles
Make sure you have your staple pair of wedges while you are on vacay baybay! Perfectly styled with flowy dresses, or lightweight pants!
- Open almond toe
- Band over the toe
- Ankle strap
- Adjustable pin buckle closure
- Faux nubuck with woven straw detailing
Style Number/Barcode: 07406-0112

Category Name: Vacation Looks

Price: $30.90

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Fever Stripe Halter Jumpsuit
Spring has come and it's ready to refresh that wardrobe with this adorable jumpsuit! Style your look with some strappy sandals and a cute boater hat!

Fits & Features
- Adjustable Halter Tie
- Plunging V Neckline
- Open Back I Elastic Paper Bag Back Waist
- Wide Leg Openings
- Woven Cotton Blend Striped Fabric
- Relax Fit I Minimal Stretch
Style Number/Barcode: 06302-0148

Category Name: Vacation Looks

Price: $6.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spring Simplicity Swiss Dot Babydoll Mini Dress
Charm them all with this sweet and simple babydoll dress! Put your hair in a cute updo and slip into some block heels for a fabulous spring look!

Fits & Features
- Scoop Neckline
- Ruffles At Sleeve Openings
- Keyhole Opening At The Back I Button Closure
- Mini Length Hemline
- Swiss Dot Woven Fabric I Fully Lined I Round Eyelet Design At The Top Front & Along Skirt
- Relaxed Fit I Minimal Stretch
Style Number/Barcode: 05102-0731

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stylish In Stripes Tassel Waist Tie Mini Dress
Leave work looking absolutely stylish in stripes with this cute mini dress! You'll love the cute drawstring tassels that cinch your waist! Slip into a pair of block heels and get your hair up into a high pony for a chic look!

Fits & Features
- V Neckline
- Button-Front
- Drawstring Waist With Tassel Detail
- Mini Length, Ruffle-Trim Hemline
- Drop Shoulder Balloon Sleeves With Elastic Cuffs
- Woven Fabric With All Over Striped Print
- Relax I Minimal Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0732

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pop Of Color Block Ditsy Floral Midi Dress
Give them a pop of color this season in this flowy dress! Add a pair of block heels and cute mini purse for an OOTD!

Fits & Features
- Tank Shoulder Straps
- Plunging V Neckline & Back
- Back Zipper With Hook & Eye Closure
- Midi Length I Overlapping Ruffle Trim Hem
- Woven Fabric With Ditsy Floral Print & Color Block Design I Partial, Mini Length Lining
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05101-0809

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunset Dream Tie Dye Satin Midi Dress
You'll look like the perf sunset dream in this tie dye midi dess! Pair with some espadrille sandals for a stylish summer time vibe.

Fit & Features
- Tie shoulder spaghetti straps
- Cowl square neckline
- Flattering horiztonal seam under the bust
- Back bar detail | Partial open back
- Flowy mid-length hem
- Tie dye satin-like fabric | Sheer woven lining
Style Number/Barcode: 05102-0737

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Denim Diva Zip Front Mini Dress
Stow your jeans and bust out a denim mini dress for the spring szn! Pair this with a lightweight long sleeve and some cute ankle booties!

Fits & Features
- Tank Shoulder Straps
- Scoop Neckline & Back
- Zipper Front I Linear Seam Details
- Mini Length Silhouette
- Denim Composition
- Form Hugging Fit I Moderate Stretch
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0471

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beauty So Bold Floral Mesh Maxi Dress
Stroll like a bold beauty in this floral mesh maxi dress for any occasion! Its strapless design and curve-hugging fit accentuate your natural beauty, while the flowing maxi hem adds elegant movement.

Fit & Features
- Bold floral print, mesh fabric, stretchy knit lining
- Strapless neckline
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000058

Category Name: Vacation Looks

Price: $9.97 $34.90

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