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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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.

Stylish Staple Ribbed Knit Bodycon Midi Dress
A stylish staple like this bodycon midi dress needs to be in your closet. The ribbed knit fabric offers plenty of stretch, while the form-hugging fit flaunts your curves.

Fit & Features
- Lined ribbed knit fabric, high stretch
- Sleeveless square neck and back design
- Spaghetti straps
- High side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000066

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: PINK

Available Size: M, L, XL
Product Badge:
- Sale
Sip Of Sultry Strapless Ruffle Mini Dress
Be the center of attention in this sultry strapless mesh mini dress! It features a strapless neckline with non-slip grip lining, and a ruffled trim adds a flirty touch while the bodycon silhouette highlights your curves down to the mini-length hem. Complete the look in heels and teardrop earrings.

Fit & Features
- Strapless neckline
- Non-slip grip lining
- Side zipper and hook-eye closure
- Ruffle trim, bodycon silhouette
- Mini-length hem
- Mesh fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-3660

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK

Available Size: S, M
Abstract Effect Strapless Bodycon Mini Dress
Every head will turn towards you in this abstract mini dress designed in a flattering bodycon silhouette that hugs your curves just right!

Fit & Features
- Abstract print, mesh-lined stretchy fabric
- Strapless neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000078

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Delightful Charm Halter A-Line Midi Dress
Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!

Fit & Features
- Woven fabric, no stretch
- Halter pleated neckline
- Open back, zipper and hook-eye closure
- Beaded tie waist
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5648

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: In Stock

Available Color: NATURAL

Available Size: S
Product Badge:
- Sale
Sunny Outlook Sun Drop Faux Pearl Earrings
Perfect for sunny days at soirees, these earrings feature sun charms with rhinestone centers and a faux pearl strand. Complete the look with a necklace.

Fit & Features
- Sun charms with rhinestone centers
- Faux pearl strand
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2053

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Kiss And Tell Sweetheart Sheer Lace Maxi Dress
Take on the night with this daring and stylish sheer lace maxi dress! Featuring a darling sweetheart neckline and form-hugging silhouette, this sheer dress will make you feel confident and sexy. The built-in padded bust and adjustable spaghetti straps provide comfort and support, while the high side slit adds a touch of boldness. Complete the look in a slip and stiletto heels.

Fit & Features
- Sheer lace fabric, slight stretch
- Adjustable spaghetti straps
- Built-in padded underwire bust
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-3076

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Simply Chic Strapless Ribbed Knit Midi Dress
Simply chic, this strapless ribbed knit midi dress is a closet staple. The asymmetric seams and form-hugging silhouette will show off your gorgeous curves.

Fit & Features
- Ribbed hacci knit fabric with knit lining, high stretch
- Strapless straight neckline
- Asymmetric seams
- Midi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5956

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling Amore Tie-Back A-Line Eyelet Mini Dress
Fall in love with this adorable eyelet mini dress perf for weekend plans. The flirty tie-back detail and ruffled A-line silhouette will get you all the compliments.

Fit & Features
- Eyelet knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Ruffled trim
- Short A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6011

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: In Stock

Available Color: WHITE-2

Available Size: L
Product Badge:
- Sale
Sensational Delight Sweetheart Cutout Midi Dress
Create a sensational look in this effortlessly chic midi dress on your next weekend getaway. The small cutout below the bust adds a touch of allure to the flowy A-line silhouette.

Fit & Features
- Cotton blend fabric lined with stretchy knit
- Sweetheart neckline, cutout below the bust
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- High waist seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5649

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Level Up Rhinestone Spiral Sandals
Level up your glamorous side in these statement-flat sandals perfect for semi-formal and dressy events! They feature an almond toe, rhinestone embellished toe and spiral ankle straps, and a faux leather footbed with rhinestone trim. Complete the look with a chic ring set.

Fit & Features
- Almond toe
- Rhinestone embellished toe and spiral ankle straps
- Faux leather footbed with rhinestone trim
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1121

Category Name: Vacation Looks

Price: $12.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Radiant Shine Cubic Zirconia Sun Pendant Necklace
Radiate the prettiest shine with this cubic zirconia sun pendant necklace! It features a delicate chain with a small sun pendant adorned with mini cubic zirconia stones at the center. Style with hoop earrings.

Fit & Features
- Dainty chain-link design
- Sun outline pendant
- Mini cubic zirconia stones
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1792

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek And Sultry Halter Jumpsuit
This halter jumpsuit brings the drama with a front twist cutout, curve-loving fit, and wide-leg silhouette made to stun on sight. Wear it to turn every room into your runway.

Fit & Features
- Halter neckline with multiple ways to style
- Cutout bodice, partially open back
- Straight leg fit with a flared hem
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0531

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: BLACK, BROWN, CHARTREUSE

Available Size: XS, S, M, L, XL
Trendy Girl Next Door Strapless Denim Mini Dress
Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!

Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Strapless straight neckline, front no-slip strip
- Back zipper with hook and eye closure
- Faux chest pockets
- Cargo flap pockets
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5524

Category Name: Vacation Looks

Price: $11.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Glam Pearl Charm Lariat Necklace
Capture the coastal glam vibe with this gorgeous pearl charm lariat necklace. It features a two-row delicate chain-link design with a flat chain layer with a pretty faux pearl charm and a ball chain lariat layer with matching faux pearl charms. Style with a dainty bracelet.

Fit & Features
- Two-row layered design
- Flat chain with faux pearl charm
- Ball chain lariat with faux pearl charms
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1811

Category Name: Vacation Looks

Price: $2.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Attention Please High-Rise Cargo Mini Skirt
Functional fashion meets a flattering silhouette with this cargo mini skirt perfect for hangs! Featuring a high-rise waist and bodycon fit, this skirt accentuates your curves. The side flap pockets and faux back pockets add a touch of utility-chic style to the twill woven fabric. Complete the look in a short sleeve tee and sneakers.

Fit & Features
- Twill woven fabric, no stretch
- High rise waist
- Front button and hidden zipper closure
- Side flap pockets, faux back pockets
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06301-0183

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sun Kissed Strapless Floral Bodycon Mini Dress
Bare your sun kissed shoulders on vacay in this strapless mini dress with a statement floral print and flattering bodycon fit that flaunts your curves!

Fit & Features
- Mesh fabric, floral print, stretchy knit lining
- Strapless neckline
- Bodycon fit
- Mini-length hem
- Runs small
Style Number/Barcode: 05102-6112

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Call Me Later Oversized Square Sunglasses
For when you're not taking calls—just compliments. These oversized square sunglasses bring bold energy with glam rhinestone side detailing and an effortlessly luxe look.

Fit & Features
- Oversized square-shaped design
- Plastic frame with glossy finish
- Thick arms with rhinestone cutout accents
- Built-in nose pads
- Tinted lenses
Style Number/Barcode: 07008-000060

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: BLACK

Available Size: NS
Eyes On The Prize Aviator Sunglasses
Giving chic energy with zero effort. These aviator sunglasses bring sharp lines and cool-girl vibes to every fit—perfect for your next content drop or post-brunch stroll.

Fit & Features
- Classic aviator silhouette
- Dark lenses
Style Number/Barcode: 07008-000044

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Day Time Adventure Puff Sleeve Cutout Linen Romper
Get ready to adventure in style with this linen romper! Made of linen blend fabric for comfort and lined with woven fabric for a polished look. It features trendy puff short sleeves and a head-turning cutout back, this romper also has hidden side pockets for keeping your hands warm and a flattering short-length hem. Complete the look in cute sandals and earrings!

Fit & Features
- Linen blend fabric, woven lining, no stretch
- Square neckline
- Cutout back
- Hidden side pockets
- Short-length
- Runs true to size
Style Number/Barcode: 06303-0264

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Seashell Cove Strappy Back Crochet Mini Dress
Channel beachy vibes with this crochet mini dress. The strappy back and bodycon silhouette enhance your curves while the wrap mini-length hem features a whimsical seashell trim.

Fit & Features
- Crochet fabric, sewn-in knit lining
- Strapless neckline, non-slip grip lining
- Strappy back with tassel strings
- Bodycon silhouette
- Wrap mini-length hem with seashell trim
- Runs true to size
Style Number/Barcode: 05102-000012

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stack It Up Resin Stretch Bracelet
Your wrist’s new plus-one. This resin stretch bracelet adds an instant pop of style, perfect for stacking or wearing solo for a minimalist moment.

Fit & Features
- Stretch elastic fit
- Lightweight and comfortable
- Easy slip-on style
- Resin material
Style Number/Barcode: 07003-000108

Category Name: Vacation Looks

Price: $11.90

Availability: In Stock

Available Color: BROWN, TAUPE

Available Size: NS
Sent A Postcard Lace-Up Print Mini Dress
A chic printed mini dress for your next cute trip! This dress is designed to turn heads with a lace-up back that adjusts to your perfect fit, statement puff sleeves, and a form-hugging fit that showcases your curves.

Fit & Features
- Printed design, woven fabric, woven lining
- Puff short sleeves
- Sweetheart neckline
- Lace-up back, lower zipper and hook-eye closure
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000113

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stack Star Resin Bangle Bracelet
The MVP of your arm candy lineup. This resin bangle brings bold, polished vibes—wear it solo for a clean statement or stack it high for instant drama.

Fit & Features
- Smooth resin material
- Classic bangle silhouette
- Solid structured fit
- Lightweight and comfortable
Style Number/Barcode: 07003-000114

Category Name: Vacation Looks

Price: $11.90

Availability: In Stock

Available Color: BROWN

Available Size: NS
Island Sun Tropical High Rise Palazzo Pants
These palazzo pants will have you feeling so tropical for your next getaway! Made from a smooth knit fabric with a tropical print, they feature a comfortable high-rise elasticized waistband and a flowy wide-leg silhouette making them perfect for packing with you. Complete the look with the matching top.

Shop Matching Top: Island Sun Tropical Tie Front Crop Top

Fit & Features
- Tropical print, smooth knit stretchy fabric
- High-rise elasticized waistband
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2457

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials