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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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.

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
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
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
Sweetly Sheer Lace Tie Front Crop Top
A little angel, a little trouble—this lace crop is your new fave layering piece. Style it over a bralette or solo for that effortlessly flirty, carefree vibe!

Fit & Features
- Sheer lace fabric
- Long sleeves with flare cuffs
- Tie front
- Ultra-cropped hem
- Bra not included
- Runs true to size
Style Number/Barcode: 06204-000021

Category Name: Vacation Looks

Price: $32.90

Availability: In Stock

Available Color: NATURAL

Available Size: L
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
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
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
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
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
Miss Jetsetter High-Rise Print Mini Skort
Whether you're jet-setting to your next adventure, meeting friends for brunch, or creating the perfect vacation look, this printed mini skort is essential for looking cute on the go! Shop the matching top to complete the look.

Shop Matching Top: Miss Jetsetter Halter Tie-Back Print Crop Top

Fit & Features
- Printed design, woven fabric, stretchy knit shorts lining
- High-rise waist, side zipper and hook-eye closure
- Skirt overlay with side tie
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06303-000021

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
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
Blissfully Cute Three Piece Headband Set
Add a finishing look to your tresses with this three-piece headband set! The set includes a denim headband with faux pearl embellishments, a chain link metal headband, and a faux pearl headband. Style with an adorable shoulder purse for any event!

Fit & Features
- Three-piece headband set
- One denim headband with faux pearls
- One chain link metal headband
- One faux pearl headband
Style Number/Barcode: 07006-0467

Category Name: Vacation Looks

Price: $3.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Go To Rhinestone Band Flat Sandals
Step into these glam rhinestone band flat sandals as your new go-to for casual plans or vacay! Featuring an almond toe and a single band adorned with sparkling rhinestones, these sandals will add a touch of glamour to any outfit. The cushioned faux leather footbed provides all-day comfort. Complete the look in a cute romper.

Fit & Features
- Almond toe
- Rhinestone embellished single band
- Rhinestone trim, flat sole
- Luxe fit faux leather cushioned footbed
- Runs true to size
Style Number/Barcode: 07404-1160

Category Name: Vacation Looks

Price: $12.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Currently In Paradise V-Neck Tropical Midi Dress
This tropical midi dress will be with you paradise for a stylishly chic vacation! Featuring a V-neckline adorned with spaghetti straps and a tie-back design, it's the perfect form-hugging dress for any island adventure. With a side slit and midi-length hem, you'll be sure to turn heads! Complete the look in wedge sandals and earrings.

Fit & Features
- Tropical print, stretchy knit fabric, sewn-in knit lining
- Spaghetti straps
- V-Neckline
- Tie-back design
- Side slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5633

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Statement Made High-Rise Dual-Slit Maxi Skirt
The statement has been made when you step out in this maxi skirt on vacay or at a pool party! The breezy knit skirt boasts a flattering high-rise elasticized waistband, a built-in cheeky lining, dual high front slits to bare some skin, and a flowy maxi-length hem. Complete the look in a flirty tie-front top and sandals.

Fit & Features
- Stretchy knit fabric
- High-rise elasticized waist
- Built-in cheeky underwear lining
- Dual high front slits
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-0975

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweetest Thing Strappy Back Halter Babydoll Dress
Experience the ultimate blend of sweet and sultry in this babydoll mini dress at shower celebrations or backyard parties! The delicate lace trim on the halter V-neckline adds a touch of femininity, while the strappy open back turns heads along the ruffled, flowy silhouette.

Fit & Features
- Woven fabric, woven lining
- Halter V-neckline, lace trim, bust tie
- Strappy open back, adjustable spaghetti straps
- Ruffled babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6036

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Eclectic Charm Teardrop Stone Necklace
Adorn your look with this eclectic necklace featuring a braided band with a teardrop stone design. Includes a back adjustable chain with a lobster clasp closure. Complete the look in a tropical dress for vacation!

Fit & Features
- Braided band
- Teardrop stone design
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1788

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charming Ways V-Neck Floral Crepe A-Line Dress
All eyes and hearts will be on you in this floral crepe mini dress all season! With puff sleeves and a mini-length hem, this dress is perfect for a playful day out. The A-line silhouette will flatter your figure, making you stand out in style. Complete the look in wedge sandals.

Fit & Features
- Floral print, crepe fabric, moderate stretch
- V-neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5700

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunshine Livin' Halter Crochet Crop Top
This crochet crop top was meant for living under the sun! Whether you're heading to a festival or a getaway, this top will keep you boho-cute. It features a sultry halter neckline with a spaghetti strap tie and an ultra-cropped hem to flaunt your figure. Complete the look with the matching pants.

Shop Matching Bottoms: Sunshine Livin' High Rise Palazzo Crochet Pants

Fit & Features
- Crochet fabric lined with stretchy knit
- Halter neckline
- Spaghetti straps
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2492

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Best For Last Halter A-Line Denim Mini Dress
Be the talk of the town in this flirty denim mini dress perfect for festivals, concerts, or country bars! The plunging halter neckline shows some skin while the flattering A-line silhouette cinches your waist and flows into a flirty flared mini hem.

Fit & Features
- Denim fabric, moderate stretch
- Plunge halter V-neckline, tie straps
- A-line silhouette
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000070

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Everyday Charmer Basic Rib Knit Maxi Dress
A basic maxi dress that brings everyday charm! This long rib knit dress features a square neckline, spaghetti straps, and a flattering bodycon silhouette, you'll love this maxi dress for any occasion. Complete the look in a cute crop jacket and your favorite sneakers!

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5522

Category Name: Vacation Looks

Price: $9.97 $34.90

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