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.

  • Retro Chic Contrast Trim Bikini Top

    Shop Matching Bottoms: Retro Chic Contrast Trim Bikini Bottoms

    Fit & Features

    • Smooth nylon-blend fabrication, plenty of stretch
    • Contrast trim design
    • Triangle-shaped cups
    • Double-row adjustable spaghetti straps
    • Tie-back bar strap
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 07104-0728

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Breezes Halter Boho Satin Maxi Dress

    Enter the room in this chic boho satin maxi dress to make a bold impression! The sleeveless dress boasts a halter neckline and a flowy silhouette adorned with a high front slit. Style with stiletto heels.

    Fit & Features

    • Boho print, satin woven fabric. sewn-in woven lining
    • Halter neckline
    • Spaghetti strap
    • Flowy silhouette
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5865

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Radiant Blooms Floral Halter Maxi Dress

    The maxi dress features a sleeveless halter neckline with halter neck ties, a large floral print, and a maxi-length hem. Complete the outfit with door knocker hoops for the perfect date outfit.

    Fit & Features

    • Lined smooth knit and mesh fabrication
    • Sleeveless halter neckline
    • Halter neck ties
    • Floral print
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3712

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Passion Sleeveless Lace-Up Maxi Dress

    The maxi dress features a sleeveless square neckline supported with additional built-in flexible boning, an abstract floral pattern, a lace-up back design, and a bold high-side slit. Complete the look with stiletto heels for the perfect date night outfit. 

    Fit & Features

    • Mesh fabric, sewn-in knit lining
    • Sleeveless square neckline
    • Built-in-boning
    • Floral pattern
    • Lace-up back design
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3773

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Hour Tortoiseshell Oval Sunglasses

    Fit & Features

    • Tortoiseshell pattern
    • Oval-shaped hard plastic frame
    • Built-in nose pads
    • Tan-hued lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1121

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Cutie Cat Eye Sunglasses

    Fit & Features

    • Hard plastic frame
    • Cat-eye design
    • Wide arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1120

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam In Motion Two-Pack Metal Hinge Bracelet

    Fit & Features

    • Pack includes two bracelets
    • Wavy metal design
    • Hinge closure

    Style Number/Barcode: 07003-0651

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beauty So Divine Floral Satin A-Line Mini Dress

    Boast a beautiful allure in this floral satin mini dress featuring a delicate lace trim and flattering A-line silhouette. Pair with heels.

    Fit & Features

    • Floral print, silky satin fabric
    • Spaghetti straps
    • Lace trim sweetheart neckline
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3778

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirtatious Scene Halter Lace Skater Dress

    Make it a flirty scene in this lace skater dress boasting a sultry halter V-neckline with metal accents and a flattering tiered ruffled mini-length hem. Complete the look with boots.

    Fit & Features

    • Lace-lined fabric
    • Halter V-neckline with metal accents
    • Skater silhouette
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4095

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Airplane Mode Script Baseball Cap

    Fit & Features

    • Traditional baseball cap fit
    • Curved brim
    • Embroidered script reading "airplane mode" 
    • Adjustable back strap with metal buckle

    Style Number/Barcode: 07302-1758

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Escape High Rise Ruched Midi Skirt

    Shop Matching Top: Coastal Escape Cropped Halter Top

    Fit & Features

    • Smooth knit fabrication with lining
    • High-rise waist
    • Ruched bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-1130

    Category Name: Vacation Looks

    Price: $9.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Destination Paradise V-Neck Floral Maxi Dress

    The perfect floral maxi dress for your next getaway! Designed in a sleeveless silhouette, this dress features a flattering V-neckline, sleek spaghetti straps, and a form-hugging fit with a flowy floor-length hem. Complete the look with earrings.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3915

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Beauty Floral Mesh Maxi Dress

    A beautiful floral mesh maxi dress for your escape to paradise! The dress boasts a flattering V-neckline and a form-hugging fit that flares into a flowy maxi-length hem. Pair with earrings and a bracelet.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4075

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Thing Tie-Back Eyelet Skater Dress

    Dressing cute is easy with this eyelet skater dress, perfect for graduates, birthdays, and any occasion that calls for all eyes on you! 

    Fit & Features

    • Eyelet woven fabric, woven lining
    • V-neckline
    • Adjustable spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4021

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Vibes V-Neck Floral Mesh Maxi Dress

    An effortless and dreamy floral mesh maxi dress to slip into for date night or dinners on vacay! The sleeveless dress is designed with a flattering V-neckline, delicate adjustable spaghetti straps, and a form-hugging fit that leads to the flowy floor-length hem. Pair with a hair accessory.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • V-neckline, adjustable spaghetti straps
    • Form-hugging fit
    • Flowy floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4012

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Update Convertible Ruched Long Dress

    The perfect sleeveless long dress to update your chic wardrobe! The dress features a convertible neckline allowing for versatile styling like a halter or an off-the-shoulder look atop the form-hugging slim silhouette. Pair with earrings.

    Fit & Features

    • Smooth knit fabric
    • Convertible neckline
    • Halter or off-the-shoulder
    • Form-hugging slim silhouette
    • Long length hem
    • Runs true to size

    Style Number/Barcode: 05102-000023

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stroll The Gardens Floral Corset Lace Skater Dress

    Stroll the gardens looking so pretty in this floral corset skater dress featuring delicate lace trim and a flattering flowy short-length hem that'll give you a dreamy feel. Pair with earrings and heels.

    Fit & Features

    • Floral pattern, woven fabric, woven lining with lace trim
    • Adjustable shoulder straps, sweetheart neckline
    • Corset bodice, underwire bust, flexible boning, lace trim
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3719

    Category Name: Vacation Looks

    Price: $9.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Weekend Vibes Crochet Knit Tote Bag

    This trendy crochet knit tote bag is perfect for those effortless weekend vibes at the beach or farmer's market! It features a breezy open crochet top pattern with a closely knitted bottom and a long shoulder strap.

    Fit & Features

    • Open crochet top pattern, knitted bottom
    • Long shoulder strap

    Style Number/Barcode: 07203-2118

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Turn Heads Abstract Print Strapless High Slit Maxi Dress

    Unveil a chic allure in this lined airy mesh maxi dress designed with an eye-catching abstract print to turn heads. It features a strapless straight-across neckline, a high-cut side slit to reveal some leg, and a fitted silhouette on the maxi-length hem.

    Fit & Features

    • Sheer mesh fabric with soft brushed knit lining, plenty of stretch
    • Abstract print
    • Strapless straight neckline
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6105

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachside Babe High-Rise Bikini Bottoms

    Capture a babe look in this bikini bottom sitting beachside! The swimsuit bottoms boast a flattering V-cut high-rise waist with an adjustable side tie so you can customize the fit and a cheeky coverage back. Pair with the matching bikini top.

    Fit & Features

    • Textured fabric
    • V-cut high-rise waist
    • Dual adjustable side ties
    • Cheeky coverage back
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0863

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Maving Waves Bandeau Textured Bikini Top

    Make waves this season and show off a cute vibe in this bikini top! The swimsuit top features a flattering strapless bandeau neckline with a hook insert and a back hook closure to secure the style. Pair with the matching bikini bottoms to complete the look!

    Shop Matching Bikini Bottoms: Making Waves High-Cut Textured Bikini Bottoms

    Fit & Features

    • Strapless bandeau neckline
    • Removable padded bra cups
    • Front hook insert
    • Back hook closure
    • Textured fabric
    • Runs true to size

    Style Number/Barcode: 07104-0716

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making Waves High-Cut Textured Bikini Bottoms

    Make waves this season and show off a cute vibe in these bikini bottoms! The swimsuit bottoms feature a flattering high V-cut waist with adjustable side ties and a cheeky coverage back. Pair with the matching bikini top to complete the look!

    Shop Matching Bikini Top: Making Waves Bandeau Textured Bikini Top

    Fit & Features

    • High V-cut waist
    • Adjustable side ties
    • Cheeky coverage
    • Textured fabric, lined
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0864

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Airy Chic Woven Wide-Leg Pants

    Airy and chic, these lightweight woven palazzo pants are the breezy staple you need for your laidback weekend plans. They feature a high-rise elasticized waistband for added stretch and a flowy wide-leg silhouette for that laid-back vibe.

    Fit & Features

    • Lightweight woven fabric, no stretch
    • High-rise elasticized waistband
    • Dual front pockets
    • Wide-leg silhouette
    • Pants in size small have a 12" front rise with a 30" inseam
    • Runs true to size

    Style Number/Barcode: 06402-1472

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Flirtatious Floral Button Skater Dress

    With a pretty floral pattern and button accents, this skater dress exudes flirtatious romance vibes! The mini-length dress boasts a flattering V-neckline, a lace-up back that turns heads, and a twirl-worthy skater silhouette. Pair with sneakers for a casual look.

    Fit & Features

    • Burnout floral pattern, woven fabric lined with stretchy knit
    • V-neckline, adjustable spaghetti straps
    • Lace-up back
    • Faux button front accents
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3229

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free