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.

  • Sultry Spice Cutout Maxi Dress

    Sultry and spicy! Make jaws drop in this sleeveless maxi dress featuring a one-shoulder neckline, waist cutout details and a form-fitting silhouette with a high-cut side slit for a show of skin. Composed of stretchy slinky knit fabric. Finish the look in lucite mules.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Waist cutout details
    • Form-fitting silhouette
    • High-cut side slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4528

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me On A Getaway Midi Dress

    Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless halter neckline, thin straps that tie at the back of the neck
    • Front ruching, adjustable drawstring
    • Front waist cutout
    • Midi-length, form-fitting silhouette, side slit
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1414

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachy Vibes Maxi Sweater Dress

    Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Open back, cross-back strap design
    • Fitted, maxi-length silhouette, side slit
    • Sweater knit fabric, crochet detailing, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1421

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Passport To Paradise Midi Dress

    The island may be breathtaking but you'll also be a sultry view in this sleeveless midi dress featuring a square neck, spaghetti straps, a cutout bodice, asymmetrical hem, and a side ruched drawstring that lets you customize the fit. Complete the look in a straw floppy hat.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Cutout bodice
    • Side ruched drawstring
    • Form-fitting
    • Asymmetrical midi hem
    • Slinky knit lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4620

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Babe Sleeveless Bodycon Slit Mini Dress

    A sleeveless knit mini dress boasts a flattering square neckline, a bodycon fit, and a flirty front slit. Perfect for layering or styling alone.

    Fit & Features

    • Knit fabric, moderate stretch
    • Square neckline
    • Shoulder straps
    • Front slit
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 06005-2002

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Leafy Greens Ruffle Skater Romper

    Wear your greens! Steal the show on vacay in this palm leaf print romper featuring a sleeveless, square neck, spaghetti straps, open back with tie closure, and a ruffled skater-style skirt with shorts lining. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open back with tie closure
    • Ruffled skater-style skirt
    • Shorts lining
    • Palm leaf print
    • Brushed knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06503-0992

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sun Dance Paisley Flare Pants

    Dance all day in these boho flare pants featuring a high-rise elasticized waist, form-fitting silhouette, and a paisley multi-print design. Complete the look in a wrap crop top. 

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting
    • Flared hem
    • Boho paisley print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0920

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy-Chic Bodycon Mini Dress

    Showcase a beachy-chic vibe in this curve-hugging bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, form-fitting silhouette. The stretchy brushed knit fabric features an all-over tropical palm leaf print. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical palm leaf print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4696

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Flower Lattice Back Dress

    Look as pretty as the island flowers in this tropical maxi dress perfect for a luau dinner! It features a sleeveless, square neck, sleek spaghetti straps, an open back with lattice detailing, a sultry side slit, and a curve-hugging silhouette. Complete your vacay look in large hoop earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lattice straps
    • Side slit, curve-hugging silhouette
    • Maxi-length hem
    • Tropical floral print, knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4506

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get That Glitzy Glow Bikini Top

    Get that glitzy glow for your weekend getaway with this trendy bikini top! It features a basic triangle design with halter spaghetti straps, tie-back straps, and a lurex glitter mesh fabric with sheer mesh inserts. Complete the look with the matching bikini bottoms.

    Shop Matching Bottoms: Get That Glitzy Glow Bikini Bottoms

    Fit & Features

    • Triangle design
    • Halter spaghetti straps
    • Tie-back spaghetti straps
    • Lurex glitter mesh fabric, sheer mesh inserts
    • No padding
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0697

    Category Name: Vacation Looks

    Price: $8.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In Line High Rise Striped Pants

    These woven striped pants should be in line with your summer aesthetic! They feature a high-rise waist, side pockets for keeping your hands warm, and a wide-leg silhouette. Complete the look in the matching top.

    Shop The Matching Top: In Line Tie-Front Striped Top

    Fit & Features

    • High-rise waist
    • Side pockets
    • Wide-leg silhouette
    • Striped woven fabric
    • Fits true to size

    Style Number/Barcode: 06302-0621

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Line Tie-Front Striped Top

    This woven striped top should be in line with your summer aesthetic! Featuring kimono-style short sleeves, a tie-front design, and a cropped hem. Complete the look in the matching pants.

    Shop Matching Bottoms: In Line High Rise Striped Pants

    Fit & Features

    • Kimono-style short sleeves
    • Tie-front design
    • Cropped hem
    • Striped woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1220

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Retro Cat Eye Sunglasses

    Sassy and retro! These oversized sunglasses feature cat-eye sleek metal frames, tinted gradient lenses, rubber most supports, and arms. Complete the look in a printed jumpsuit for a party.

    Fit & Features

    • Oversized style
    • Cat-eye sleek metal frame
    • Tinted gradient lenses
    • Rubber nose supports and arms
    • 100% UV protection

    Style Number/Barcode: 07008-0952

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paradise Ready One-Shoulder Maxi Dress

    This gorgeous tropical printed maxi dress will have you looking ready for a vacay off to paradise! It features a sleeveless one-shoulder neckline, a single bungee spaghetti strap, an asymmetrical waist cutout with a chic O-ring accent, and a curve-hugging, floor-length silhouette with a front slit. The stretchy knit fabric features an all-over palm leaf print. Complete your look with slip-on sandals and your fave shades.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single bungee spaghetti strap
    • Asymmetrical waist cutout, O-ring accent
    • Maxi-length hem, form-fitting silhouette, front slit
    • Tropical palm leaf print
    • Knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4484

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Hopping Tropical Maxi Dress

    Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.

    Fit & Features

    • Sleeveless, halter neck with tie
    • Cutout bodice
    • Open-back, tie closure
    • Side slit
    • Flowy maxi silhouette
    • Tropical print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4500

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Away On Vacay Tropical Mini Dress

    Going away on vacation? This tropical mini dress will definitely get you in the vacay mood! It features a sleeveless, scoop neck, spaghetti straps, a form-hugging silhouette, and a side ruched seam that leads to the asymmetrical slit hem. Complete the look in chic oversized sunnies.

    Fit & Features

    • Sleeveless, scoop neck
    • Spaghetti straps
    • Form-hugging silhouette
    • Side ruched seam, asymmetrical slit hem
    • Mini-length 
    • Tropical print, sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4682

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Vacay Sleeveless Maxi Dress

    Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless plunging V-neck and back design
    • Tank shoulder straps
    • High-rise banded waist, side cutouts
    • Maxi-length hem, flowy silhouette
    • Front slit
    • Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4504

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Summer Halter Maxi Dress

    Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • O-ring inset, cutout accent
    • Bodycon silhouette
    • Asymmetrical slit
    • Maxi-length hem
    • Rib-knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4467

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Effect Abstract Cowl Halter Crop Top

    Printed to perfection in a flattering halter silhouette, this crop top boasts a sultry cowl neckline and an open back to show some skin! Pair with the matching pants.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Cowl halter neckline, tie straps
    • Open back
    • Fitted crop hem
    • Runs true to size

    Shop The Matching Pants: Sultry Effect Abstract Wide-Leg Pants

    Style Number/Barcode: 06001-000107

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kaleidoscope Boho Tie-Front Top

    Escape the city life for paradise with this boho crop top featuring a sleeveless, sweetheart neck, adjustable spaghetti straps, a tie-front detail, back smocked design, and a kaleidoscope print. Complete the look in the matching skirt. 

    Shop Matching Skirt: Kaleidoscope Boho Slit Maxi Skirt

    Fit & Features

    • Sleeveless, sweetheart neck
    • Adjustable spaghetti straps
    • Tie-front detail
    • Back smocked design
    • Kaleidoscope boho print
    • Runs true to size

    Style Number/Barcode: 06003-1556

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Twist Halter Knit Romper

    This halter romper comes with a playful twist! Featuring a sleeveless, keyhole halter neckline with cross straps, tie closure, a partial open-back, high-rise waist, and a flowy short hem. Complete the look in chic espadrille wedges.

    Fit & Features

    • Sleeveless, halter neckline, tie-closure
    • Cross front straps, keyhole
    • Partial open-back
    • Flowy short hem
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06503-0995

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Kaleidoscope Boho Slit Maxi Skirt

    Escape the city life for paradise with this boho maxi skirt featuring a high-rise waist, front high-cut slit, and a kaleidoscope print. Complete the look in the matching top.

    Shop Matching Top: Kaleidoscope Boho Tie-Front Top

    Fit & Features

    • High-rise waist
    • Front high-cut slit
    • Maxi-length hem
    • Kaleidoscope boho print
    • Runs true to size

    Style Number/Barcode: 06301-0103

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love It Lace-Up Crop Top

    You'll love this lace-up crop top that is an elevated version of your fave basic tanks. It features a sleeveless square neckline, spaghetti straps, a lattice-front design, and a cropped, form-hugging fit. Style with high-rise denim and cute mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up front, tie closure
    • Cropped fit
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06003-1861

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless And Chic Cropped Blouse

    This effortless and chic cropped blouse is a stunning summer staple! It features a sweetheart neckline with a lace-up tie-front design, half-length bishop sleeves, ruched detailing, and a cropped fit. Style with high-rise denim.

    Fit & Features

    • Sweetheart neckline
    • Lace-up tie-front design
    • Half-length sheer bishop sleeves, elasticized hems
    • Ruching
    • Back zipper closure
    • Cropped fit
    • Sheer woven fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1878

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance