Vacation Looks

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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.

  • Casual Staple Mock Neck Tank Top

    This basic ribbed knit tank top is a casual staple to create the cutest looks! It features a sleeveless mock neckline, tank shoulder straps, and a fitted cropped hem. The lightweight ribbed knit fabric offers plenty of stretch. Style with your favorite pair of denim and hoop earrings.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Fitted cropped hem
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1587

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend By The Bay Cotton Wide-Leg Pants

    Create a chic relaxed look for a weekend by the bay in these lightweight cotton wide-leg pants. They feature an elasticized high-rise waist with an adjustable front drawstring, dual front pockets, and a casual wide-leg silhouette. The cotton fabric has no stretch. Pair with a crop top and sandals.

    Fit & Features

    • Elasticized high-rise waist
    • Adjustable front drawstring
    • Dual front pockets
    • Wide-leg silhouette
    • Cotton fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0773

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Sultry Vibes Cutout Maxi Dress

    Bring the casual sultry vibes to your weekend plans with this curve-hugging maxi dress. It features a sleeveless sweetheart neckline with a twist-front design, spaghetti straps, a bold waist cutout at the front, a maxi-length hem with a chic back slit accent, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules for drinks with the girls.

    Fit & Features

    • Sleeveless sweetheart neckline, twist-front design
    • Spaghetti straps
    • Waist cutout
    • Maxi-length hem, back slit
    • Bodycon fit
    • Ribbed knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5186

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Cutout Midi Sweater Dress

    Create the perfect casual chic look with this of-the-moment sweater dress. It features a sleeveless scoop neckline with contrast piping, thin tank shoulder straps, a front waist cutout with matching contrast piping, a midi-length hem with a front slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules.

    Fit & Features

    • Sleeveless scoop neckline, contrast piping
    • Thin tank shoulder straps
    • Front waist cutout, contrast piping
    • Midi-length hem, front slit
    • Curve-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1700

    Category Name: Vacation Looks

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Happy Face Statement Sunglasses

    Complete your fab summer festival 'fits with these trendy statement sunnies! The sunglasses feature round-tinted lenses with a heart-eyed happy face cutout design, sleek metal arms, and rubber nose pads for support. Style with a rhinestone choker necklace.

    Fit & Features

    • Round-tinted lenses
    • Heart-eyed happy face cutout design
    • Thin metal arms
    • Rubber nose pads
    • Polycarbonate, blocks 100% UV

    Style Number/Barcode: 07008-1032

    Category Name: Vacation Looks

    Price: $2.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Heartbreaker Statement Sunglasses

    You'll be a total heartbreaker this season in these fabulous statement sunglasses. They feature heart-shaped black-tinted lenses with a dripping design, sleek metal arms, and rubber nose pads for support. Style with a layered choker necklace and hoop earrings for a summer concert.

    Fit & Features

    • Heart-shaped black-tinted lenses
    • Dripping design
    • Thin metal arms
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1034

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Butterfly Babe Rhinestone Statement Sunglasses

    Style up your summer festival 'fits with these trendy statement sunglasses! They feature a butterfly design with no frame, pink flower accents, gemstones, and rhinestones on each side, sleek metal arms, and rubber nose pads for support. Pair with charm earrings and a choker necklace!

    Fit & Features

    • Butterfly design, no frame
    • Pink tinted lenses
    • Pink flower accents, gemstones, rhinestones
    • Thin metal arms
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1035

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Flair Flat Top Square Sunglasses

    Give your summer 'fits an edgy flair with these cool shades. The sunglasses feature a flat top square-shaped design, a plastic frame with metal geometric accents on each side, and tinted lenses. Style with a cropped denim jacket.

    Fit & Features

    • Flat top
    • Square-shaped design
    • Plastic frame
    • Metal geometric side accents
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1020

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Girl High Rise Wide Leg Pants

    Showcase island vibes on vacation in these must-have tropical pants perfect for chilling under the cabana with a cocktail in hand! They feature a flattering high-rise waist, slim hip-hugging fit, a wide-leg silhouette, and a breezy palm print. Complete the look in platform sandals.

    Fit & Features

    • High-rise waist
    • Slim hip-hugging fit
    • Wide-leg silhouette
    • Palm print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2355

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Allure Geometric Cat-Eye Sunglasses

    Give off a chic allure in these sleek shades! The sunglasses feature a small geometric cat-eye design with a plastic frame, metal chain-link accents on the arms, and tinted lenses. Style with hoop earrings.

    Fit & Features

    • Small geometric cat-eye shape
    • Plastic frame
    • Metal chain-link accents on the arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1025

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ultra-Chic Small Rectangular Frame Sunglasses

    Show off an ultra-chic look in these sleek of-the-moment sunglasses. They feature a small geometric rectangular-shaped design with a plastic frame, metal square-shaped accents on the arms, and tinted lenses. Style with a crossbody bag. 

    Fit & Features

    • Small geometric rectangular-shaped design
    • Plastic frame
    • Metal square-shaped accents on the arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1030

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Level Up Rectangular Frame Sunglasses

    Level up your look for the summer season with these trendy shades! The sunglasses feature a geometric rectangular-shaped design with a plastic frame and tinted lenses. Style with a layered charm necklace. 

    Fit & Features

    • Geometric rectangular-shaped design
    • Plastic frame
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1029

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Things Up Cutout Mini Dress

    Heat things up in this showstopping bodycon mini dress on vacation or at a summer party! It features a sweetheart neckline, spaghetti straps that crisscross in the back, dual front center O-ring inserts and cutout accents, side ruched seams, and a fitted hem. Complete the look with geo-shaped earrings and a layered necklace.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps, crisscross back
    • Dual front center O-ring inserts, cutout accents
    • Bodycon silhouette, side ruched seams
    • Mini-length fitted hem
    • Double-lined brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5137

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend State Of Mind Long Cotton Vest

    Get into a weekend state of mind with this chic long cotton vest. It features a sleeveless bodice with a lapel collar, a button-down front, a thin tie-front detail, front pockets, and a long-line hem with a fitted silhouette. Layer this lightweight vest over a mini dress with espadrille sandals.

    Fit & Features

    • Sleeveless bodice, lapel collar
    • Button-down front
    • Thin tie-front detail
    • Dual front pockets
    • Long-line hem, fitted silhouette
    • Cotton fabric, sewn-in woven lining
    • Runs true to size

    Style Number/Barcode: 06204-1595

    Category Name: Vacation Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Knit Your Average Crochet Sweater Mini Dress

    Elevate your look to a subtle shine factor in this crochet sweater mini dress perfect for layering over your bikini on vacation or a private yacht party! It features a sleeveless cowl neckline, halter tie-back straps, a partially open back, and a bodycon fit. The dress is composed of a space dye metallic sheer knit fabric. Style with strappy sandals.

    Fit & Features

    • Sleeveless cowl neckline
    • Halter tie-back straps
    • Partially open back
    • Bodycon fit
    • Mini-length hem
    • Space dye metallic sheer knit fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06005-1659

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Perfection Knit Halter Crop Top

    This casual ribbed sweater knit crop top is the perfect basic for everyday styling! It features a sleeveless halter neckline with spaghetti straps, an open back with a cross-back strap design, and a fitted cropped hem. The sweater knit fabric offers plenty of stretch. Pair with a mini skirt and mules.

    Fit & Features

    • Sleeveless halter neckline
    • Spaghetti straps
    • Open back, cross-back strap design
    • Fitted cropped hem
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1367

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Back To Cool High-Rise Parachute Joggers

    Take your street style back to cool in these parachute joggers perfect for adding to your everyday rotation! They feature a high-rise elasticized waist with an adjustable drawcord, hidden side pockets, a relaxed silhouette, and a drawcord hem so you can customize the style. Complete the look in a basic crop tee and sneakers.

    Fit & Features

    • High-rise elasticized waist
    • Adjustable drawcord
    • Hidden side pockets
    • Relaxed silhouette
    • Drawcord hem
    • Lightweight nylon fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0737

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Glam Vibe Pearl Denim Jacket

    This chic pearl denim jacket will give off a trendy glam vibe! It features a collared neckline, fab faux pearl embellishments on the shoulders, long sleeves with button cuffs, a button-down front, chest pockets, and a cropped hem with a relaxed fit. Layer over a fitted bodysuit with matching denim shorts for the coolest look.

    Fit & Features

    • Collared neckline
    • Faux pearl embellishments
    • Long sleeves, button cuffs
    • Button-down front, dual chest pockets
    • Cropped hem, relaxed fit
    • Light wash rigid denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0507

    Category Name: Vacation Looks

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Allure Watercolor Print Bra Top

    Showcase a bold allure and draw all the attention in this trendy watercolor-printed bra top. It features a sweetheart neckline with a padded bust and structured underwire for support, long fitted sleeves, and an ultra-cropped fitted hem with a lower back adjustable strap The sheer mesh fabric offers plenty of stretch. Style with high-rise jeans and strappy mules for a fab happy-hour vibe! 

    Fit & Features

    • Sweetheart neckline, padded bust, structured underwire
    • Long fitted sleeves
    • Ultra-cropped fitted hem
    • Lower back adjustable spaghetti strap
    • Watercolor print
    • Sheer mesh fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4752

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Vibes Sleeveless Scoop Neck Bodysuit

    Bring the casual vibes to your everyday 'fits with this sleeveless bodysuit. Featuring a scoop neckline, thin tank shoulder straps, a matching scoop-back design, and a form-hugging fit, this bodysuit can effortlessly be styled for whatever you have planned. The knit fabric features a textured pattern and offers plenty of stretch. Pair with denim shorts and a flowy duster for a cute weekend look.

    Fit & Features

    • Sleeveless scoop neckline
    • Thin tank shoulder straps
    • Scoop-back design
    • Form-hugging fit
    • Knit fabric, textured pattern, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1550

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Howdy Cutie Straw Cowboy Hat

    Everyone will be saying howdy to you looking so cute in this straw cowboy hat at festivals! It features a classic wide and curved brim and an adjustable beaded string. Style with a flirty crochet top and printed pants.

    Fit & Features

    • Classic wide and curved brim
    • Adjustable beaded string
    • Cowboy style
    • Straw material

    Style Number/Barcode: 07302-1372

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Mood Cutout Bodycon Midi Dress

    Keep your summer style sultry and on-trend with this curve-hugging bodycon midi dress. It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric cutout that continues all around the waist with a sleek O-ring accent at the front, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Pair with strappy heels.

    Fit & Features

    • Sleeveless square neckline
    • Thin tank shoulder straps
    • Asymmetric cutout, all around the waist, metal O-ring accent
    • Midi-length hem
    • Bodycon fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5189

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Nautical Vibes Striped Mini Dress

    Elevate your summer style and give off chic nautical vibes in this striped mini dress! It features a sleeveless scoop neckline, spaghetti straps, a faux wrap waist design with a tie-front detail, a mini-length hem, and a form-hugging fit. The stretchy brushed knit fabric features an all-over horizontal striped pattern. Complete the look with espadrille sandals for a beachside brunch!

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Faux wrap waist design, tie-front detail
    • Mini-length hem, form-hugging fit
    • Horizontal striped print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5067

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Girlie Crochet Chevron Sweater Dress

    Calling all the sunshine girlies! Slip on this playful crochet chevron sweater dress for backyard pool parties or vacations. It features a sleeveless halter V-neckline, tie-back spaghetti straps, an open back, a bodycon silhouette, and a mini-length hem with ribbed trim. Style with chunky platform heels for a complete look!

    Fit & Features

    • Sleeveless halter V-neckline
    • Tie-back spaghetti straps
    • Open back
    • Bodycon silhouette
    • Mini-length hem with ribbed trim
    • Chevron pattern, crochet sweater fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1658

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale