Vacation Looks

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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.

  • Sunny Dreams High-Rise Distressed Denim Shorts

    Keep it cute and casual all season in these denim shorts from fun at the beach to weekend hangs! They feature a flattering high-rise waist, trendy distressed accents along the form-hugging silhouette, and a raw cut-off hem. Complete the look in a basic tee and sneakers!

    Fit & Features

    • Denim material with stretch
    • High-rise waist
    • Distressed accents
    • Form-hugging
    • Front button and hidden zipper closure
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-0397

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Poolside Flirt String Bikini Top

    Sit flirty and pretty in this eyelet string bikini top at a pool party or on vacation! Pair with the matching bikini bottoms.

    Fit & Features

    • Eyelet lined fabric
    • Triangle cups
    • Dual string spaghetti back ties
    • Runs true to size 

     

    Shop The Matching Bikini Bottoms: Poolside Flirt Eyelet String Bikini Bottoms

    Style Number/Barcode: 07104-0719

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serve Attitude Cat Eye Sunglasses

    These aren’t just sunglasses—they’re your armor of IDGAF. With a sleek cat eye shape that oozes retro cool and mystery, these frames instantly upgrade your fit and your mood.

    Fit & Features

    • Cat eye frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000065

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Striped Halter V-Neck Mini Dress

    This striped mini dress will easily become your perfect favorite piece this season! The halter V-neckline and open back highlight your alluring figure, while the bodycon fit and mini-length hem flatters your curves on the striped mesh-lined fabric. Complete the look with sunglasses and sandals for a day out or on vacation!

    Fit & Features

    • Striped print, mesh fabric, soft stretchy knit lining
    • Halter V-neckline
    • Open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5811

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Chic High Slit Crochet Maxi Skirt

    Create a sunny chic 'fit with the cutest crochet maxi skirt! Designed with a breezy sheer crochet knit fabric with a built-in panty lining, this skirt was made for summer getaways. It features a high-rise banded waist with a front adjustable drawstring for a customized fit, a high-cut back slit, and a slim-fit silhouette. Complete your look with the matching crop top and a pair of slip-on sandals!

    Shop Matching Top: Sunny Chic Halter Ruched Crochet Crop Top

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • Built-in knit panty lining
    • High-rise elastic banded waist
    • Front adjustable drawstring
    • High back slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 06501-0917

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Vibes High Slit Tropical Knit Maxi Dress

    Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!

    Fit & Features

    • Stretchy knit fabric with a bust lining
    • Tropical print
    • Sleeveless V-neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5537

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Covetable Charm V-Neck Ruffled Maxi Dress

    You'll covet the charm of this sleeveless maxi dress all season!  With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.

    Fit & Features

    • Woven fabric, bust lining, no stretch
    • Adjustable spaghetti straps
    • Crisscross and smocked back
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5546

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Think Sunshine Long Sleeve Cutout Crochet Mini Dress

    Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Crochet fabric, sewn-in knit lining, slight stretch
    • Sheer flared long sleeves
    • V-neckline
    • Hoop insert, cutout waist and back
    • Tie-back design
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5732

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Company Sleeveless Button-Up Vest

    Never worry about looking stylish with this sleeveless vest in your lineup! Designed from a linen-blend woven fabric, this vest offers a classic and trendy vibe with a collar neckline, button-up front closures, faux pockets, and a cropped hem. Complete the look in denim shorts.

    Fit & Features

    • Linen-blend woven fabric, no stretch
    • Collar neckline
    • Button-up front closures
    • Buttoned chest pockets
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1785

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meant To Be Surplice V-Neck Strappy Chiffon Romper

    This chiffon romper was meant to be adored by everyone at showers or celebrations! The surplice V-neckline and adjustable spaghetti straps provide a flattering fit, while the crisscross open back adds a touch of playful charm. The tie waist cinches in at the perfect spot, and the layered ruffled short-length hem adds a flirty and feminine touch. Complete the look in wedge sandals.

    Fit & Features

    • Textured chiffon fabric, chiffon woven lining
    • Surplice V-Neckline, adjustable spaghetti straps
    • Criss-cross open back, zipper and hook-eye closure
    • Layered ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 06403-0418

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Daydream Butterfly Chain Belt

    Soft girl energy? Activated. This butterfly chain belt flutters right into your faves with dreamy layered charms and delicate movement—perfect for cinching your waist with a little fairycore flair.

    Fit & Features

    • Chain-link design
    • Small and large butterfly charm accents
    • Adjustable fit with lobster clasp closure

    Style Number/Barcode: 07301-000144

    Category Name: Vacation Looks

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Paradise One-Shoulder Tropical Maxi Dress

    You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.

    Fit & Features

    • Stretchy knit fabric, knit lining at the bust
    • Tropical print
    • Asymmetric one-shoulder neckline, spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5542

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Prowl Strapless Zebra Crop Top

    On the prowl and ready to unleash fierceness in this zebra print crop top! It features a strapless neckline, a tie-back design, and a fitted crop hem that flaunts your figure. Complete the look with the matching skirt.

    Shop Matching Skirt: On The Prowl High Rise Zebra Maxi Skirt

    Fit & Features

    • Zebra print, woven fabric, bust knit lining
    • Strapless neckline
    • Tie-back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2507

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Never A Dull Moment Strapless Cutout Maxi Dress

    Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Cutout bust, strappy back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5766

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress

    Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.

    Fit & Features

    • Palm leaf tropical and border print, woven fabric with lining, no stretch
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • A-line maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5864

    Category Name: Vacation Looks

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Sun Floral Bikini Bottoms

    Enjoy the sweet sunshine at the pool or beach in these floral bikini bottoms! Pair with the matching bikini top.

    Fit & Features

    • Floral print, knit lined fabric
    • Low-rise waist
    • Ruffle trim
    • Cheeky bottom
    • Returns are not accepted without the hygienic liner
    • Runs true to size

     

    Shop The Matching Bikini Top: Sweet Sun Floral Tie-Front Bikini Top

    Style Number/Barcode: 07105-0867

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacation Queen High-Rise Slit Tropical Maxi Skirt

    Unleash your inner vacation queen with this tropical maxi skirt! Made from stretchy knit fabric, this skirt is perfect for any tropical adventure with its eye-catching palm print. Its high-rise waist and flowy silhouette will flatter your figure, while the high front slit adds a touch of sass. Complete the look with sandals.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, bikini brief lining
    • High rise waist
    • High front slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-0967

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All-Day Slay Oversized Cat-Eye Sunglasses

    Show off an all-day slay in these sleek cat-eye sunglasses! They feature an oversized cat-eye design with a thin metal frame, sassy leopard-printed arms, and tinted lenses. Style these chic shades with hoop earrings.

    Fit & Features

    • Oversized cat-eye design
    • Thin metal frame
    • Leopard-printed arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1066

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City In Style Rhinestone Trim Sunglasses

    Stroll the city in these stylish sunglasses for a trendy allure. They feature tinted lenses with rhinestone trim for a hint of glam, rubber nose supports, and a comfortable fit. Complete the look in a basic midi dress for shopping and grabbing coffee!

    Fit & Features

    • Tinted lenses with rhinestone trim
    • Rubber nose supports
    • Comfortable fit
    • 100% UV protection

    Style Number/Barcode: 07008-1079

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Distraction Low Rise Ruffled Mini Skirt

    Be a playful distraction in this low-rise mini skirt this summer! Crafted from jacquard pattern woven fabric, it's the perfect way to make a stylish statement with a touch of whimsy. Features a low-rise waist paired with a tiered ruffled silhouette creating a flirty mini-length hem. Complete the look in a crop top and platform sneakers!

    Fit & Features

    • Jacquard pattern, woven fabric lined with stretchy knit
    • Low rise waist
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0674

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Babe Ditsy Floral Cropped Tube Top

    Radiate sunny vibes in the cutest cropped tube top! Designed with an adorable ditsy floral print on stretchy smocked knit fabric, it features a strapless straight-across neckline, a cropped hem, a dainty ruffled trim, and a form-hugging fit. Style with denim shorts and sneakers.

    Fit & Features

    • Ditsy floral print
    • Stretchy smocked ribbed knit fabric
    • Strapless straight neckline
    • Cropped hem
    • Ruffled trims
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1901

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living In The Palms Wide Leg Palazzo Pants

    Escape to a tropical island in these breezy palm print palazzo pants perfect for dinners with a view or exploring with a cocktail in hand! These pants have a flattering high-rise elastic waistband and wide-leg silhouette for style and comfort on stretchy knit palm print fabric. Complete the look with the matching top.

    Shop Matching Top: Living In The Palms Tie-Front Crop Top

    Fit & Features

    • Palm print, stretchy knit fabric
    • High-rise elastic waistband
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2462

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crushin' On You Lace Trim Babydoll Floral Crop Top

    Look and feel like a precious flirt in this babydoll crop top! Made from an airy mesh fabric with an adorable floral print, this top features a delicate lace trim V-neckline, spaghetti straps, and a layered ruffled crop hem. Complete the look in denim shorts and sandals for casual plans!

    Fit & Features

    • Floral print, mesh fabric, bust lining
    • Spagehtti straps
    • Lace trim V-neckline
    • Layered ruffled crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5413

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Prowl High Rise Zebra Maxi Skirt

    On the prowl and ready to unleash fierceness in this zebra print maxi skirt! It features a flattering high-rise waist with an elastic banded back for added stretch, a high front slit to show some leg, and a flowy maxi silhouette. Complete the look with the matching top.

    Shop Matching Top: On The Prowl Strapless Zebra Crop Top

    Fit & Features

    • Zebra print, woven fabric
    • High-rise waist with elastic banded back
    • High front slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06301-0191

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale