Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Bloom Baby Floral Halter Cutout Mini Dress

    Soft, flirty, and ready for golden hour—this halter mini dress is a little bit sweet, a little bit daring. Flowy ruffles and a smocked waist keep the vibe effortlessly pretty for sunset dinners or dressy events!

    Fit & Features

    • Floral print, chiffon woven fabric, woven lining
    • Sweetheart twist halter neckline, tie straps
    • Cutout bust accent
    • Stretchy, smocked, fitted bodice
    • Drop waist seam
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000243

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Slip Into Something Floral Mesh Maxi Dress

    The dress you “accidentally” wear to steal the spotlight. This floral mesh maxi drapes you in a soft cowl neckline with a low back and curve-hugging fit that’s ready for cocktails at sunset!

    Fit & Features

    • Floral print, mesh fabric, soft and stretchy knit lining
    • Cowl halter neckline with tie straps
    • Low cut back
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000341

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L, XL

  • Trendy Shades Square Sunglasses

    Discover these trendy sunglasses perfect for any sunny day to keep your style on point! They feature a small square shape, tinted UV protective lenses, and comfortable arms and nose support. Complete the look with platform sneakers for a casual day out.

    Fit & Features

    • Small square shape
    • Tinted UV protective lenses
    • Comfortable arms and nose support

    Style Number/Barcode: 07008-1089

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out In The Wild Leopard Crop Top

    You could chill… but why would you? This halter top is made for turning heads with a draped cowl neckline and chainlink moment that screams “she knows she’s the vibe.”

    Fit & Features

    • Leopard print, stretchy mesh knit fabric
    • Cowl halter neckline, hoop inserts, spaghetti strap tie
    • Open back with spaghetti strap tie
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000198

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Weekend Feeling Sleeveless Bubble Hem Mini Dress

    A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.

    Fit & Features

    • Knit fabric, moderate stretch
    • Crew neckline
    • Form-hugging fit
    • Drop waist seam, bubble mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5873

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt In Full Bloom Lace Halter Top

    A little sheer, a little sweet—this lace halter brings all the romance with a ring-front detail and breezy flyaway silhouette. Pair with denim or maxi skirts for your next IG-worthy moment.

    Fit & Features

    • Lace fabric, bust knit lining
    • Halter neckline, spaghetti strap ties
    • Hoop insert
    • Center split design
    • Sheer cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000161

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Ruffle Me Up Midi Skirt

    Flirty, flowy, and made for vacay vibes! This ruffle-trim midi skirt brings soft drama with a sleek fit and side slit that shows just enough—pair it with the matching top to complete the look.

    Shop The Matching Top: Ruffle Me Up Crop Top

    Fit & Features

    • Smooth double-lined stretchy knit fabric
    • High-rise waist
    • Side ruched seam and ruffled slit
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000060

    Category Name: Vacation Looks

    Price: $28.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Easygoing Chic Puff Sleeve Tie Front Top

    You'll feel easygoing and chic in this linen-like top for any weekend plans or on vacay! With its playful puff sleeves and breezy open front design featuring dual tie-fronts, this top is the perfect addition to your summer wardrobe. Pair with the matching skort.

    Fit & Features

    • Linen-like woven fabric, sewn-in knit lining
    • Puff short sleeves
    • Open front design, dual tie-front
    • keyhole back with button closure, stretchy smocked panel
    • Mid-length hem
    • Runs true to size

     

    Shop The Matching Skort: Easygoing Chic High-Rise Wrap Tie Skort

    Style Number/Barcode: 06003-000003

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: RED

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Stole Your Heart Charms Shield Sunglasses

    These shield sunglasses will steal your heart! They showcase side heart charms for a trendy vibe, oversized tinted lenses, rubber nose supports, and comfortable arms. Complete the look in a cute jumpsuit.

    Fit & Features

    • Shield style oversized tinted lenses
    • Side heart charms
    • Rubber nose supports
    • Comfortable arms

    Style Number/Barcode: 07008-1093

    Category Name: Vacation Looks

    Price: $5.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle and Ready Chiffon Halter Maxi Dress

    Love to make an entrance? Nail it with this chiffon maxi dress! With cascading ruffles, sultry cutouts, and a leggy slit, this chiffon maxi brings the drama every time.

    Fit & Features

    • Chiffon fabric, lined with stretchy knit
    • Sweetheart halter neckline with tie straps, padded bra cups
    • Cutout back and sides
    • Cascading ruffle trims
    • Flowy silhouette, front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000198

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: BROWN, BEIGE

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Adorable Chic Bow Cutout Bodycon Mini Dress

    Adorable chic and ready to be seen, this sleeveless mini dress is everything! It features adjustable spaghetti straps for a customizable fit, a sweetheart neckline adorned with a statement bow, and a cutout bust to show a peak of skin along the bodycon silhouette. Complete the look in high heels.

    Fit & Features

    • Smooth knit fabric lined with knit
    • Adjustable spaghetti straps
    • Sweetheart neckline with bow
    • Cutout bust
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5697

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Chic Thong Square Toe Heels

    From daytime outings to nights out, these thong heels are perfect for dressing up any look for every occasion! 

    Fit & Features

    • 2" short kitten heel
    • Square toe
    • Thin thong toe strap
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000058

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: PINK, TAN

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • Best Seller
  • Lowkey Head Turner Open Back Mini Dress

    She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.

    Fit & Features

    • Rib knit fabric, smooth, stretchy knit lining
    • Crew neck
    • Open back with tie detail
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000159

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sunny Daze Linen Tie-Front Crop Top

    Catch the breeze, catch the vibe. This linen tie-front crop top is made for sunny days and carefree moments—easy, airy, and ready for wherever the day takes you.

    Shop Matching Bottoms: Sunny Daze Linen Mini Skort

    Fit & Features

    • Linen woven fabric
    • Sleeveless V-neckline
    • Tank shoulder straps
    • Tie-front design
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000023

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Catching Looks Crochet Palazzo Pants

    Serving body and beach energy all in one slay. These crochet palazzo pants feature a high-rise waist and sheer wide-leg silhouette, perf for sipping cocktails, catching sunsets, or just catching looks.

    Shop Matching Top: Catching Looks Crochet Bandeau Tube Top

    Fit & Features

    • Sheer crochet fabric with panty lining
    • High-rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000008

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Part of a Set
  • Effortless Style Short Sleeve Ribbed Knit Crop Top

    This adorable short sleeve crop top will make everyday styling effortless. Made with stretchy double-lined ribbed knit, it features a classic crew neckline, short sleeves, and a fitted cropped hem. The perf basic, pair with straight-leg jeans and sneakers.

    Fit & Features

    • Stretchy double-lined ribbed knit fabric
    • Crew neckline
    • Short sleeves
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1859

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Daze Linen Mini Skort

    Catch the breeze, catch the vibe. This linen mini skort is made for sunny days and carefree moments—easy, airy, and ready for wherever the day takes you.

    Shop Matching Top: Sunny Daze Linen Tie-Front Crop Top

    Fit & Features

    • Linen woven fabric
    • Mid-rise waist
    • Mini-length overlay, A-line silhouette
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06303-000034

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Just Your Stripe Off-The-Shoulder Crop Top

    This striped crop top is just what you're looking for! It's designed on stretchy rib knit fabric with a trendy striped print, an off-the-shoulder neckline to bare some skin, and a flirty cropped hem. Complete the look in denim shorts for casual plans.

    Fit & Features

    • Striped rib knit stretchy fabric
    • Off-the-shoulder neckline
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-1972

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Babe High-Rise Slit Maxi Skirt

    From farmer's market to the beach, this flowy maxi skirt is ready to create stylish looks for any adventure! With a flattering high-rise waist, a flirty front slit, and a tiered silhouette, this skirt is essential for spring to summer.

    Fit & Features

    • Chambray woven fabric
    • High-rise waist
    • Front slit
    • Tiered flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06301-0208

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

    Product Badge:
    • Best Seller
  • Eyes on You Abstract Print Cutout Mini Dress

    You didn’t just enter the room—you owned it. With a bold cutout and curve-hugging fit, this iconic abstract print mini dress is your go-to for nights out where the vibe is flirty and fearless.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract print
    • Sleeveless sweetheart neckline, padded bra cups
    • Bust cutout with lattice design, large waist cutout
    • Adjustable spaghetti straps
    • Ruching, mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000288

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • All Day Vibe Mid-Rise Denim Capri Pants

    Elevate your casual style in these denim capri pants, perfect for any adventure! The flattering mid-rise waist sits perfectly on your hips, while the form-hugging fit showcases your silhouette with front seam detailing that creates a leg-lengthening effect.

    Fit & Features

    • Dark wash denim fabric
    • Mid-rise waist
    • Front seam detailing, form-hugging fit
    • Capri-length hem
    • Front button closure, belt loop accents
    • Back pockets
    • Runs true to size

    Style Number/Barcode: 06602-0563

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: S, M, L

  • Cute Classic Denim Shortall

    Cute and classic, these denim shortalls are an effortless staple with a relaxed fit and trendy cuffed hem.

    Fit & Features

    • Medium wash denim fabric
    • Adjustable shoulder straps
    • Racerback design
    • Front bib pocket
    • Side button closures, belt loop accents, front pockets
    • Relaxed fit, cuffed hem
    • Runs true to size

    Style Number/Barcode: 06603-0485

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: S, M, L

  • Feeling Fun Cuffed Denim Mini Skirt

    Forever classic with a fun touch, this denim mini skirt boasts a flattering bodycon fit and a unique cuffed hem. Pair with a cute top for a farmer's market!

    Fit & Features

    • Denim fabric
    • High-rise waist, belt loops
    • Front button and hidden zipper closure
    • Dual front and back pockets
    • Mini-length cuffed hem
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06601-000002

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Dancing Moves High-Rise Side Ruffle Midi Skirt

    Dance all night in this midi skirt featuring a flattering high-rise waist, form-hugging silhouette, and a high side slit with a flirty ruffled trim perfect for styling with heels. The smooth knit fabric hugs your curves and offers plenty of stretch.

    Fit & Features

    • Smooth knit-lined stretchy fabric
    • High-rise waist
    • High-side slit with ruffle trim
    • Form-hugging
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-1063

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale