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.

  • Fierce And Fiesty Wrap Mini Dress

    Take a walk on the wild side in the Fierce And Fiesty wrap mini dress! It features a plunging v-neckline with a wrap tie design at the waist, long bell sleeves, and a mini-length silhouette with ruffle trim. The garment is composed of smooth satin and features tiger-inspired print design, offering little to no stretch. Zipper not included. 

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0646

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Metallic Leopard Ruched Mini Dress

    You can never have enough leopard print! This dress features a sweetheart bustier top with padded cups, lace-up detail down the front, a square back, long, unlined sleeves with elastic shoulders, and a ruched mini-length silhouette. The garment is made of chiffon and showcases leopard and metallic detailing throughout. It has a fully lined body and offers little to no stretch. Zipper at back. 

     Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0647

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Extra Chain Link Necklace
    Girl you're extra and we're loving it! The necklace features a chunky single row chain link design. Perfectly pair this piece with your favorite bold and extra looks!

    Style Number/Barcode: 07002-0186

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Rise Distressed Boyfriend Jeans
    We love a good distressed pair of denim! These high rise boyfriend jeans feature the traditional five pocket and belt loop design, a front button and hidden zipper closure, slight destructed detailing down the leg, and a tapered leg fit. The jeans offer moderate stretch.

    Style Number/Barcode: 06602-0054

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chiffon Long Sleeve Knot Front Mini Dress

    What's knot to like? This darling dress features a plunging v-neckline, long bell sleeves, decorative knot at the center, and a mini-length silhouette. Crafted from chiffon and fully lined at the front body, it showcases a print design with metallic detailing throughout and offers little to no stretch. Zipper not included. 

     Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

    Style Number/Barcode: 05101-0451

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chiffon Floral Surplice Mini Dress

    Look effortlessly chic in this billowy mini dress! With a ditsy floral print throughout, this dress showcases a plunging v-neckline, surplice style middle, and long sleeves with elastic ruffle cuffs. The tiered, shirred, and fully lined skirt features self ties and an adjustable zipper at the side. This chiffon crafted dress offers little to no stretch. 

     Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0447

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spot On A-Line Midi Dress

    Throw on a cozy knit sweater, add a pair of boots, and your outfit will be looking spot on! Showcasing a smudge spot print, the sleeveless bodice features adjustable shoulder straps and a v-neckline. Decorative buttons trail down the front, leading to a center split. Linen crafted, this dress features an A-line silhouette and offers little to no stretch. Zipper at center back. 

     Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0301

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Satin Leopard Print Mini Dress

    On the hunt for the perfect mini? Look no further than this sassy satin number. Featuring adjustable spaghetti straps and a square neckline, it also showcases a tonal leopard print and a daring slit at front. Fully lined, it offers minimal stretch and a zipper at the back.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0359

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked Off The Shoulder Mini Dress

    Radiate in this sweet smocked piece! This linen dress features an off the shoulder design with ruffle trim, billowy sleeves with elastic cuffs, smocking at the midsection, and a pleated hem. It showcases a mini-length silhouette with a form hugging fit. Does not include zipper and has a moderate stretch. 

     Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0375

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sealed With Charm Short A-Line Dress

    Seal your look with this charming A-line dress for a rehearsal dinner or sunset dinner date! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, a padded bust, and a flattering short-length hem. Complete the look in chic block heels.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Padded bust
    • A-line silhouette
    • Short-length hem
    • Poplin fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3152

    Category Name: Vacation Looks

    Price: $7.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bebesita Ball Cap
    You can be my bebesita. This hat says it all. The hat features a baseball cap design, a script graphic that reads: "Bebesita" in a contrasting hue and an adjustable back with metal hardware.

    Style Number/Barcode: 07302-0111

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fur Babe Rhinestone Slides
    Step out in style babygirl! Slip on these slides and head out! They are designed with a round toe, a single band over the toes that is detailed with faux fur. They have a flat form and a rhinestone detailing around the sole.

    Style Number/Barcode: 07408-0028

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fur Babe Rhinestone Slides
    Step out in style babygirl! Slip on these slides and head out! They are designed with a round toe, a single band over the toes that is detailed with faux fur. They have a flat form and a rhinestone detailing around the sole.

    Style Number/Barcode: 07408-0027

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Knotted Leopard Print Headband
    Lend your look a little animal style with this perennially chic leopard print headband. It's made from a silky fabric with contrast grosgrain tips and features a top knot detail.

    Style Number/Barcode: 07006-0102

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Large Barrette Clips Variety Pack

    Keep hair in place to achieve a sleek look with these must have clips! This variety pack includes six large metal barrettes that feature rose gold, silver and gold hues. Their easy snap clip design makes them easy to create gorgeous styles in minutes! 

    Style Number/Barcode: 07006-0839

    Category Name: Vacation Looks

    Price: $0.73 $2.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tied To Spots Mini Dress

    Get tied to this cute leopard mini dress! It features a sleeveless bodice, a scoop neckline, spaghetti tie straps and a mini length silhouette. Dress is composed of an unlined lightweight woven fabric with a leopard print pattern throughout. Garment offers a relaxed fit with minimal stretch. Zipper not included.  

     

    Style Number/Barcode: 05101-0485

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Soft And Cozy PJ Romper

    Soft and fuzzy, this adorable PJ romper couldn't get anymore cozy. It features long sleeves, a scoop neckline, a half button up front, and fitted shorts. The fuzzy faux fur fabric has minimal stretch.

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 07103-0013

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropics Vibe Plunging Mini Dress

    Transport to an island paradise with this vacay ready mini dress! It features a plunging wrap V neckline with a knot accent, long bell sleeves and asymmetrical mini length silhouette. The all over tropical print features palm leaves throughout. Dress is composed of an unlined lightweight woven fabric that offers a relaxed fit with minimal stretch. 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

     

    Style Number/Barcode: 05102-0427

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keeping It Fierce Snake Mini Dress

    Keep it fierce in snake print! The bodycon features an off the shoulder neckline with ruffled trim, short sleeves, a sweetheart bust, a keyhole with tie front accent, a smocked back and a mini length silhouette. Dress features a snake print to perfectly matching with your favorite solid pieces. Garment is composed of a lined satin fabric that offers a relaxed fit with slight stretch. 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

     

    Style Number/Barcode: 05102-0421

    Category Name: Vacation Looks

    Price: $9.97 $50.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Leopard Chiffon Maxi Dress

    Keep it sassy in spots with this pretty leopard maxi dress! It features a sleeveless bodice, a plunging wrap V neckline, adjustable spaghetti straps that lead to a strappy back design and a relaxed fit bodice that leads to a sweeping maxi length with a ruffled hem. Dress is composed of a semi sheer chiffon fabric that reveals a mini length knit lining. Garment offers a relaxed fit with a minimal stretch. Hidden back zipper closure included.

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0413

    Category Name: Vacation Looks

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fur Babe Rhinestone Slides
    Step out in style babygirl! Slip on these slides and head out! They are designed with a round toe, a single band over the toes that is detailed with faux fur. They have a flat form and a rhinestone detailing around the sole.

    Style Number/Barcode: 07408-0021

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Satin Floral Jacquard Mini Dress

    Slip into this pretty mini dress to make a sweet statement! It features a sleeveless bodice, a square neckline, spaghetti straps and a flowy slip design with a mini side slit. Dress is composed of an unlined satin-like fabric adorned with a floral design throughout. Garment offers a relaxed fit with minimal stretch. Zipper not included.

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

     

    Style Number/Barcode: 05103-0553

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serious About Snake Print Hair Clip
    If you are seriously as into snake print as we are, then you need this hair clip in your life! Designed with a faux leather material and a snap closure.

    Style Number/Barcode: 07006-0103

    Category Name: Vacation Looks

    Price: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The One You Need Mini Dress

    Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.

     Fit & Features

    • Sleeveless V-neckline
    • Thin bungee straps
    • Strapless bra recommended
    • Mini-length bodycon silhouette
    • Ribbed knit fabric
    • Figure-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-0500

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale