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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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.

Born To Be Coveted Mid-Rise Lace-Up Denim Skort
A coveted summer style starts with this mid-rise denim skort perfect for casual plans! Made from denim fabric, this skort is perfect for showing off your legs in a flirty mini-length hem. Its mid-rise waist and form-hugging fit will accentuate your curves, while the playful skirt overlay with lace-up detailing and a slit adds a touch of edginess. Complete the look in a flirty crop top and sneakers.

Fit & Features
- Denim medium wash fabric, no stretch
- Mid-rise waist
- Back zipper hook-eye closure
- Lace-up, slit accent
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0379

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Untamed Nights Halter Slit Maxi Dress
Glam meets wild in this sultry halter maxi dress. With its curve-hugging fit, statement hardware, and bold slit, it’s made for spotlight entrances and after-dark drama.

Fit & Features
- Animal print, knit-lined fabric with stretch
- Halter neckline, hardware insert, spaghetti strap tie
- Bodice cutout with hardware insert
- High front slit
- Form-hugging silhouette, maxi hem
- Runs true to size
Style Number/Barcode: 05102-000294

Category Name: Vacation Looks

Price: $45.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Golden Hour Seashell Sandals
Vacay vibes in every step. These shell-accented sandals are your new go-to for beach walks, brunch looks, and everything in between—comfy, cute, and made for your golden hour moments.

Fit & Features
- Faux leather material
- Open square-shaped toe
- Thong strap design
- Metal shell accent
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-000020

Category Name: Vacation Looks

Price: $16.90

Availability: Out of Stock
Product Badge:
- Ships Free
City Of Love V-Neck Ruffle Babydoll Dress
Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.

Fit & Features
- Woven fabric
- Ruffled shoulder straps
- Side pockets
- Babydoll silhouette
- Ruffled tiered short-length hem
- Runs true to size
Style Number/Barcode: 05102-5423

Category Name: Vacation Looks

Price: $21.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blooming Chic Flower Detail Faux Leather Block Heels
Create a blooming chic 'fit perfect for the season with these cute block heels! Made with smooth faux leather, they feature an open square-shaped toe, a detailed toe strap with faux leather flower accents and faux pearl center beading, thin adjustable ankle and heel straps, and a sleek thin block heel. Style with the matching crossbody bag for an adorable look!

Shop Matching Bag: Blooming Chic Flower Detail Clear Crossbody Bag

Fit & Features
- 3" Thin block heel
- Faux leather upper
- Open square toe
- Toe strap, faux leather flower accents, faux pearl beading
- Adjustable ankle and heel straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4702

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blissful View High Rise Crochet Midi Skirt
Enjoy stylish bliss in this crochet midi skirt on your next getaway or weekend outing! The skirt offers a flattering high-rise elasticized waist, a bodycon silhouette, and a midi-length hem. Complete the look with the matching top.

Shop Matching Top: Blissful View Halter Crochet Crop Top

Fit & Features
- Crochet fabric lined with knit
- High-rise elasticized waist
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1048

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Exceptional Taste Large Hoop Earrings
Your exceptional taste will show in these large hoop earrings that perfectly accessorize every outfit! Complete the look in a cocktail dress for a rehearsal dinner or dressy party.

Fit & Features
- Large hoops
- Omega closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2018

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Blooming Allure Floral Mesh Cutout Tube Top
Giving goddess vibes with a flirty twist. This floral mesh crop top brings all the drama with its sleek bandeau fit and daring back O-ring cutout.

Shop Matching Bottoms: Blooming Allure Floral Mesh High-Slit Maxi Skirt

Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Strapless straight-across neckline
- O-ring back cutout
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000235

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: MULTI

Available Size: XS, S, M, L
Product Badge:
- Part of a Set
Sultry Style Halter Cutout Wide-Leg Jumpsuit
Show off a sultry style on vacay or a weekend getaway in this cutout wide-leg jumpsuit! Designed with a stretchy smooth knit fabric with a full-length lining, it features a sleeveless plunging halter neckline, spaghetti straps with a tie-back design, and an alluring cutout bodice for a bold babe vibe. The fitted high waist leads to a hip-hugging fit and a trendy wide-leg silhouette. Complete the look with platform wedges.

Fit & Features
- Smooth knit fabric with knit lining, plenty of stretch
- Plunging halter neckline with tie closure, partial open back
- Cut out bodice
- Hip-hugging fit
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-2515

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Unfazed Babe Oversized Square Sunglasses
A pair of sunglasses featuring an oversized design, tortoise pattern, tinted lenses with 100% UV protection, and nose supports. Perfect for everyday wear.

Fit & Features
- Oversized design
- Tortoise pattern
- Tinted lenses
- 100% UV protection
- Nose supports
Style Number/Barcode: 07008-1102

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress
Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!

Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Cowl neckline
- Adjustable spaghetti straps
- Low back with criss-cross straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5645

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Social Girlie High Rise Slit Midi Skirt
Your social calendar is filling up and this midi skirt is here to help! Featuring a high-rise waist, side adjustable drawstring, and bodycon fit, this skirt will accentuate your curves and flatter your figure. The high-side asymmetrical slit adds a touch of intrigue while the midi-length hem keeps it chic. Complete the look in sandals.

Fit & Features
- Smooth knit stretchy fabric
- High rise waist
- Bodycon fit
- Adjustable drawstring
- Asymmetrical high side slit
- Runs true to size
Style Number/Barcode: 06501-1039

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cute Sight Cateye Metal Sunglasses
This pair of sunglasses features a cateye design on a sleek metal frame, tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.

Fit & Features
- Cateye design, sleek metal frame
- Tinted lenses
- 100% UV protection
- Rubber nose supports
Style Number/Barcode: 07008-1105

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Destination Straw Tote Bag
Whether you're heading on vacay or to the beach, this large straw tote bag will keep you stylish for whatever destination! Its spacious, adjustable drawstring interior lining and pockets make it perfect and functional for keeping your things in while the convenient top handles make it easy to carry around. Complete the look in trendy sandals.

Fit & Features
- Straw material
- Spacious, adjustable drawstring lined interior
- Interior pocket
- Top handles
- Large silhouette
Style Number/Barcode: 07203-1989

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wildflower Energy Cowl Halter Romper
This sheer mesh halter romper mixes floral and animal vibes for a look that’s flirty, fierce, and ready for your next night out!

Fit & Features
- Floral and leopard mix print, mesh-lined fabric
- Halter cowl neckline, spaghetti strap tie
- Open strappy back
- Built-in mini shorts with flirty skirt overlay
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 06503-000082

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: LEOPARD

Available Size: S, M, L
Product Badge:
- Back In Stock
Flirty Moves Ruffled Tie-Front Knit Crop Top
Make major flirty moves and create an enticing aura in this ruffled tie-front crop top! Designed with a stretchy smooth knit fabric, it features a sultry V-neckline with a tie-front design, ruffled hems for that girly flair, spaghetti straps, and an asymmetric cropped hem. Style with the matching midi skirt for a girl's night out!

Shop Matching Bottoms: Flirty Moves Ruffled Slit Knit Midi Skirt

Fit & Features
- Double-lined stretchy smooth knit fabric
- V-neckline, tie-front design
- Ruffled hems
- Spaghetti straps
- Asymmetric cropped hem
- Runs true to size
Style Number/Barcode: 06001-5451

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Seamless Sculpt Bandeau Bra
A bandeau bra designed to stretch with your body while offering a seamless and sculpting fit. This bra features a strapless neckline for no-fuss wear, removable padded bra cups that shape and support, and a seamless design on buttery smooth knit fabric. Style this bandeau with smooth shapewear shorts for a sleek silhouette.

Fit & Features
- Seamless, buttery smooth knit fabric
- Strapless neckline
- Removable padded bra cups
- Runs true to size
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: 07102-0327

Category Name: Vacation Looks

Price: $7.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty Style Beaded Stretch Bracelet Set
Adorn your wrist with this pretty and stylish bracelet set! It features three stretchy bracelets with varying sleek beaded designs. Complete the look with trendy sandals for any occasion or plan!

Fit & Features
- Three stretchy bracelets
- Varying beaded designs
Style Number/Barcode: 07003-0572

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty Bold One-Shoulder Floral Mesh Crop Top
Pretty and bold, this sleeveless crop top features a one-shoulder neckline, an adjustable side drawstring, and an asymmetrical-cut hem. The mesh fabric showcases a bold floral print.

Fit & Features
- Floral print, mesh fabric lined with mesh, stretchy
- One-shoulder neckline
- Adjustable side drawstring
- Asymmetrical-cut cropped length hem
- Runs true to size
Style Number/Barcode: 06001-5482

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Match Sleeveless Striped Ribbed Knit Mini Dress
You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

Fit & Features
- Striped pattern
- Ribbed knit fabric with moderate stretch
- Scoop neckline
- Tank shoulder straps
- Cutout back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1940

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Endless Vacay High Rise Wide-Leg Trouser Pants
Get ready for vacay packing these trouser pants for endless fun under the sun! Whether you're island hopping in Greece or sipping a mai tai on the beach, these pants will keep you so trendy. It boasts a flattering high-rise waist with side pockets for keeping your hands warm, a breeze wide-leg silhouette, plus a button front and hidden zipper closure to secure the style. Complete the look with the matching top.

Shop Matching Top: Endless Vacay Strapless Tube Crop Top

Fit & Features
- Texture woven fabric
- High-rise waist
- Wide-leg silhouette
- Side pockets
- Front button and hidden zipper closure
- Runs true to size
Style Number/Barcode: 06402-1405

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make Hearts Flutter Short Sleeve Cutout Maxi Dress
You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.

Fit & Features
- Gauze woven fabric, short knit stretchy lining
- Flutter short sleeves
- Plunge V-neckline and V-cut back
- Elasticized strappy waist with side cutouts
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5719

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Picture Perfect V-Neck Smocked A-Line Midi Dress
You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

Fit & Features
- Woven fabric lined with non-stretch woven
- Tie spaghetti straps
- V-neckline
- Stretchy smocked bodice
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3560

Category Name: Vacation Looks

Price: $11.97 $64.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Crush Striped Crochet Bralette Top
POV: you just found your new fave beach-to-brunch vibe. This striped crochet bralette top serves laid-back heat with an open back and tie details made for turning heads from sunrise to sunset.

Shop Matching Bottoms: Summer Crush Striped Crochet Midi Skirt

Fit & Features
- Crochet knit fabric
- Striped pattern
- Sleeveless triangle bust design
- Thin shoulder straps
- Open back, tie-back design
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000034

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: S, M, L
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