Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Destined For Love Lace-Up Short Skater Dress

    You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.

    Fit & Features

    • Burnout pattern, mesh fabric, tulle and stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Lace-up, back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3319

    Category Name: Vacation Dresses & Outfits

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

  • Heart It Oversized Round Sunglasses

    You'll totally heart these trendy oversized round sunglasses! They feature a round shape with a sleek plastic frame and arms, the cutest heart-shaped cutout design accented on the arms, built-in nose pads for support, and tinted lenses. Style these shades with a charm necklace.

    Fit & Features

    • Oversized round-shape
    • Plastic frame and arms
    • Heart-shaped cutout design
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1081

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Glamour Steps Rhinestone Strappy Flat Sandals

    Add glamour to your steps in these faux leather flat sandals showcasing a sparkling rhinestone embellished trim, round toe, and rhinestone-embellished strappy design with an adjustable ankle strap with buckle closure. Complete the look in a casual bodycon dress for a day out and about!

    Fit & Features

    • Flat sole
    • Faux leather material
    • Round toe
    • Rhinestone trim
    • Rhinestone embellished strappy design
    • Adjustable ankle strap, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1158

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

  • Too Cool Contrast Trim Faux Leather Sneakers

    These faux leather sneakers are too cool for school! Kick back in these exclusive shoes featuring a round toe and lace-up placket for a perfect fit. A cool contrast trim for added style and a comfortable footbed and rubber insole. Complete the look with a zip-up hoodie for casual plans.

    Fit & Features

    • Round toe
    • Lace-up placket
    • Contrast trim
    • Comfortable footbed
    • Rubber insole
    • Runs true to size

    Style Number/Barcode: 07407-0225

    Category Name: Vacation Dresses & Outfits

    Price: $28.90

    Availability: Out of Stock

  • Chic Factor Oversized Sunglasses

    Amp up the chic factor of your everyday 'fits with these sleek oversized sunglasses. They feature an oversized slightly angled design with a thin gold metal frame and nose bridge, thin gold metal arms with long cutouts, tinted lenses, and built-in nose pads for support. Pair these stylish shades with hoop earrings.

    Fit & Features

    • Oversized angled design
    • Thin gold metal frame and nose bridge
    • Thin gold metal arms with long cutouts
    • Tinted lenses
    • Built-in nose pads

    Style Number/Barcode: 07008-1097

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • The Best Yet Sleeveless Crew Neck Slit Maxi Dress

    The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!

    Fit & Features

    • Soft knit fabric, short lining, plenty of stretch
    • Sleeveless crew neckline
    • Tank straps
    • Side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5588

    Category Name: Vacation Dresses & Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Casual Scene Crew Neck Midi Dress

    Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.

    Fit & Features

    • Crew neck, short sleeves
    • Cutout waist, knot accent
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Smooth cotton knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5765

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Western Showdown Etched Concho Belt

    Saddle up with this playful etched concho belt, featuring an adjustable lobster clasp closure. Wrangle up some Western vibes and complete the look in denim shorts for a festival or concert!

    Fit & Features

    • Etched concho belt
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1113

    Category Name: Vacation Dresses & Outfits

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Escape Lace-Up Tropical Midi Dress

    Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical print, lined knit fabric, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Asymmetric high-cut hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5564

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

  • Luxe Flair Woven Loop Satin Scarf

    Add a luxe flair to your spring and summer 'fits with this woven loop satin scarf! Designed with a silky satin material with a chic woven loop pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with chunky gold hoop earrings.

    Fit & Features

    • Non-stretch satin material
    • Woven loop pattern

    Style Number/Barcode: 07305-0491

    Category Name: Vacation Dresses & Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Breeze Chain Printed Satin Scarf

    Add a luxe flair to your spring and summer 'fits with this woven chain-printed satin scarf! Designed with a silky satin material with a chic woven chain pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with high-rise denim shorts.

    Fit & Features

    • Satin chain printed woven scarf
    • Multiple styling options

    Style Number/Barcode: 07305-0500

    Category Name: Vacation Dresses & Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Getaway Tropical Print Maxi Skirt

    This alluring tropical print maxi skirt will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a high-rise waist, a maxi-length hem with a sultry high-cut side slit, and a slim-fit silhouette. Style with the matching crop top for your next destination vacay!

    Shop Matching Top: Gorgeous Getaway Tropical Print Crop Top

    Fit & Features

    • High-rise waist
    • Maxi-length hem
    • High-cut side slit
    • Slim-fit silhouette
    • Tropical print
    • Sheer mesh fabric, full-length knit lining
    • Runs true to size

    Style Number/Barcode: 06501-0956

    Category Name: Vacation Dresses & Outfits

    Price: $24.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Chasing The Sun Banner Woven Satin Scarf

    Chase this sun banner silky woven scarf for the perfect look for your next sweet escape! Designed with a silky satin material with a chic sun banner pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with a sultry jumpsuit.

    Fit & Features

    • Sun banner print
    • Woven satin fabric
    • Multiple styling options

    Style Number/Barcode: 07305-0499

    Category Name: Vacation Dresses & Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Getaway Tropical Print Crop Top

    This alluring tropical print crop top will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a sleeveless plunging V-neckline, halter spaghetti straps, a tie-front design under the bust, and a cropped, ruffled, babydoll hem with a flowy fit. Style with the matching maxi skirt for your next destination vacay!

    Shop Matching Bottoms: Gorgeous Getaway Tropical Print Maxi Skirt

    Fit & Features

    • Sleeveless plunging V-neckline
    • Halter spaghetti straps
    • Tie-front design
    • Cropped, ruffled, babydoll hem, flowy fit
    • Tropical print
    • Sheer mesh fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-5074

    Category Name: Vacation Dresses & Outfits

    Price: $19.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Free Riders Colored Stone Chain Belt

    Accessorize your ride with this statement western chain belt featuring unique colored stones, oval-shaped charms, and an adjustable lobster clasp closure to secure the style. Complete the look in a fitted mini dress.

    Fit & Features

    • Colored stones
    • Oval-shaped charms
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1146

    Category Name: Vacation Dresses & Outfits

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Soaked Cutie Satin Scarf Top

    Let the sun kiss your shoulders in this cute satin paisley scarf top perfect for festivals or weekend getaways! Featuring a strapless neckline and a tie-back design, style with denim shorts for an effortless look.

    Fit & Features

    • Silky non-stretch satin fabric
    • Paisley print
    • Strapless straight neckline
    • Smocked back, tie-back design
    • Angled hem
    • Runs true to size

    Style Number/Barcode: 06003-2732

    Category Name: Vacation Dresses & Outfits

    Price: $26.90

    Availability: In Stock

    Available Color: NAVY, RUST

    Available Size: S, M, L, XS

  • Boardwalk Crop Denim Jacket

    Stroll the boardwalk before your sunset dinner in this streetwear-inspired crop denim jacket featuring long sleeves with buttoned cuffs, a collared neckline, four-button front closure, flap pockets, distressed accents, and a pull tab button closure along the hem. Complete the look in breezy wide-leg pants and a bodysuit.

    Fit & Features

    • Non-stretch denim fabric
    • Long sleeves, buttoned-cuffs, collared neckline
    • Four-button front closure
    • Flap pockets, buttons
    • Distressed accents
    • Pull tab button closure along crop hem
    • Runs true to size

    Style Number/Barcode: 06203-0540

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Style Zebra Print Mini Skirt

    Show off a wild style in this trendy zebra print mini skirt! It features a high-rise waist, a ruched front seam leading to a chic slit, a mini-length hem, and a form-hugging fit. Complete the look with the matching crop top and a pair of clear heels.

    Shop Matching Top: Wild Style Zebra Print Crop Top

    Fit & Features

    • High-rise waist
    • Ruched front seam
    • Front slit
    • Mini-length hem, form-hugging fit
    • Zebra print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0786

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Cubic Zirconia Studs Set

    Glam up your look with this cubic zirconia stud earrings set. This pack of six varying-sized studs gives you the option of how much bling you want to rock for the day. Perfect to dress up an everyday outfit to go run errands. Pair with a chic bodysuit and distressed denim and you'll be all ready to go!

    Fit & Features

    • Cubic zirconia
    • Post-back closures, rubber stoppers
    • Set of six studs

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-3731

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ardell Demi Wispies Lashes 5 Pack

    Glam up your eyes with these gorgeous lashes. The Ardell Demi Wispies lashes offer a natural, long feathered and glamorous look, are easy to apply, and are even reusable! Perfect for your next sexy night out outfit like a sultry crop top and mini skirt. The lashes work best for large and deep-set eyes. Don't forget to pick up the eyelash glue! 

    Fit & Features

    • Long, feathered natural look
    • Reusable 
    • Includes 5 sets of eyelashes
    • Eyelash glue sold separately

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07307-0372

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: Out of Stock

  • Beautiful Bliss Floral Sequin Mesh Babydoll Dress

    Get swept up in the beauty of this babydoll dress perfect for brides-to-be, wedding showers, and dressy soirees! The sheer 3/4 length puff sleeves and square neckline add a touch of romance, while the babydoll silhouette and short hem create a playful and flirty look. The floral embroidery and sequins on the sheer mesh overlay add a touch of whimsy to this stunning dress. Complete the look with a chic ring set and heels!

    Fit & Features

    • Sheer mesh overlay line with woven fabric
    • Floral embroidery, sequin embellishments
    • Back zipper and hook-eye closure
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3357

    Category Name: Vacation Dresses & Outfits

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Sparkle Large Hoop Earrings

    Give off a stunning sparkle when these hoops catch the light! These hoop earrings feature beautiful crystal-like details to top off all your looks with a bit of bling. Topped with post-back closures for easy wear. Style these sleek hoops with a chic bodysuit and high waist jeans for an effortlessly put-together look.

    Fit & Features

    • Large hoop design
    • Cyrstal-like details 
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-0105

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Here To Slay One-Shoulder Cutout Knit Crop Top

    This iconic crop top was here to stay and slay your 'fits! Made with a stretchy ribbed knit fabric, it features an asymmetric one-shoulder neckline with a tank strap, a trendy twist-front design and sultry center bust cutout, and a cropped hem with a form-hugging fit for a snatched look. Style with high-rise jeans and sneakers for a cute and casual vibe!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Asymmetric one-shoulder neckline, tank strap
    • Twist-front design
    • Bust cutout
    • Cropped
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1950

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Covetable Charm Strapless Mini Skater Dress

    From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.

    Fit & Features

    • Poplin stretchy fabric, sewn-in knit lining
    • Back zipper and hook-eye closure
    • Strapless square neckline
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3082

    Category Name: Vacation Dresses & Outfits

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, NAVY

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

    Product Badge:
    • Sale