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.

  • Coastal Chic Starfish Dangle Earrings

    Fit & Features

    • Dangle design
    • Textured starfish charm
    • Fish hook closure

     

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

    Style Number/Barcode: 07001-2329

    Category Name: Vacation Dresses & Outfits

    Price: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutely Charming One-Shoulder Crop Top

    Go ahead and strut your cute and charming self in this sleeveless crop top to elevate your basics collection! It boasts a one-shoulder neckline with a cinch detail, and a fitted crop hem on stretchy rib knit fabric. Complete the look in a denim midi skirt and sandals!

    Fit & Features

    • Stretchy rib knit fabric
    • One-shoulder neckline
    • Tank strap with cinch detail
    • Fitted crop length hem
    • Runs true to size

    Style Number/Barcode: 06002-1909

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spill The Secrets Abstract Print Halter Top

    For when your outfit's louder than your group chat. This abstract print mesh halter top is light, effortless, and made for catching stares you weren’t even trying for.

    Fit & Features

    • Mesh fabric, high stretch
    • Abstract print
    • Sleeveless plunge V-neckline
    • Tie-front detail under the bust, front flyaway design
    • Halter spaghetti straps, tie-back design, partially open back
    • Mid-length hem, flowy fit
    • Runs true to size

    Style Number/Barcode: 06001-000162

    Category Name: Vacation Dresses & Outfits

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Fierce Allure Leopard Print Mesh Maxi Dress

    Flaunt a fierce allure in this curve-hugging leopard print maxi dress! The airy sheer mesh fabric lined with knit offers plenty of stretch and showcases a leopard print pattern for a sultry-chic vibe. The long dress features a sleeveless V-neckline, spaghetti straps, a form-fitting silhouette to accent your gorgeous curves, and a maxi-length hem. Style with strappy mules for a rooftop happy hour.

    Fit & Features

    • Leopard print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3328

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom With Grace Lace-Up Maxi Dress

    This floral mesh maxi stuns with a draped cowl neckline and lace-up back that’s perfect for making heads turn at weddings, formals, or any RSVP that matters.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Cowl neckline
    • Spaghetti straps
    • Lace-up back
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000187

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L, XL

    Product Badge:
    • Best Seller
  • Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top

    Wildly sultry is exactly how you'll look in this leopard rose mesh crop top on a night out!  The flared long sleeves and V-neckline with tie closure give a playful touch, while the center slit adds a touch of allure. The cropped length and striking leopard rose print make this top a must-have for any bold fashionista. Complete the look with the matching skirt.

    Shop Matching Bottoms: Wildy Sultry High Rise Leopard Floral Maxi Skirt

    Fit & Features

    • Leopard rose print, sheer mesh fabric, moderate stretch
    • Flared long sleeves
    • V-neckline
    • Tie-front closure and center slit
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06202-0472

    Category Name: Vacation Dresses & Outfits

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can’t Talk, Busy Strutting Block Heel Mules

    These mules are giving legs for days. With sleek thong straps, a comfy block heel, and a padded insole, this pair takes you from brunch to rooftop drinks without missing a step.

    Fit & Features

    • Block heel
    • Faux leather material
    • Open square-shaped toe
    • Thong strappy design
    • Open back, on-and-off styling
    • Padded insole
    • Runs true to size

    Style Number/Barcode: 07401-000091

    Category Name: Vacation Dresses & Outfits

    Price: $28.90

    Availability: In Stock

    Available Color: WHITE, NUDE

    Available Size: 10, 8.5, 9

  • Own The Moment Tube Floral Maxi Dress

    Ready to shut down the vacation pics? This strapless floral maxi dress brings effortless chic with a curve-hugging fit and leg-baring side slit.

    Fit & Features

    • Floral print, mesh-lined fabric, moderate stretch
    • Strapless tube neckline
    • High side slit
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000237

    Category Name: Vacation Dresses & Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

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

  • Wildy Sultry High Rise Leopard Floral Maxi Skirt

    Wildly sultry is exactly how you'll look in this leopard rose mesh maxi skirt on a night out! The skirt boasts a flattering high-rise waist complimented by a bodycon silhouette that accentuates your curves along the midi-length hem. Complete the look with the matching top.

    Shop Matching Top: Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top

    Fit & Features

    • Leopard floral print, mesh fabric lined with stretchy knit
    • High-rise waist
    • Hip-hugging fit
    • Maxi-length 
    • Runs true to size

    Style Number/Barcode: 06501-1052

    Category Name: Vacation Dresses & Outfits

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Crush Striped Crochet Tie-Front Crop Top

    Made for sandy toes and sun-kissed selfies. This striped crochet crop top is your go-to for beach days, boat days, and flirty getaways—just add SPF and salty waves.

    Fit & Features

    • Crochet fabric, striped pattern
    • Plunging V-neckline
    • Tie-front design
    • Long bell sleeves
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000019

    Category Name: Vacation Dresses & Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Knock Knock Statement Earrings

    Bold enough to stand out, chic enough to wear on repeat. These geometric door knocker earrings bring vintage vibes with a modern twist—and they're ready to elevate everything.

    Fit & Features

    • High-shine metal finish
    • Chunky geometric hoop design
    • Door knocker-inspired silhouette
    • Post back closure

     

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

    Style Number/Barcode: 07001-000039

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Sultry Fave Halter Cowl Neck Floral Maxi Dress

    You'll always embody sultriness in this floral mesh maxi dress perfect for weddings or cocktail parties! The halter cowl neckline with tie adds a touch of charm, while the form-hugging silhouette highlights your curves. The maxi-length hem and floral print mesh fabric bring an elegant and romantic touch. Complete the look with rhinestone earrings and a clutch.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Halter cowl neckline with tie
    • Form-hugging silhouette
    • Maxi-length
    • Runs true to size

    Style Number/Barcode: 05101-3331

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stacked To Perfection Beaded Stretch Bracelets

    Level up your stack game with zero effort. These beaded stretch bracelets are giving luxe layering vibes with that cool-girl ease you love.

    Fit & Features

    • Multi-pack beaded bracelets
    • Varying sizes
    • Stretchy design

    Style Number/Barcode: 07003-000051

    Category Name: Vacation Dresses & Outfits

    Price: $13.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making Waves Shell Claw Clip Set

    Not your average hair clip—these shell-shaped claws bring full glam to your grab-and-go moments. Whether you're throwing your hair up for errands or adding a little luxe to your vacation look.

    Fit & Features

    • Two-pack claw clip set
    • High-shine metal material
    • Seashell design

    Style Number/Barcode: 07006-000077

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Such A Flirt Sweetheart Lace Trim Skater Dress

    This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.

    Fit & Features

    • Sheer chiffon woven fabric with stretchy knit lining
    • Lace trim sweetheart neckline with bow detail, bust underwire
    • Adjustable lace trim shoulder straps
    • Partially smocked back with zipper and hook-eye closure
    • Lace trim bodice, drop waist seam
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3461

    Category Name: Vacation Dresses & Outfits

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Daze Straw Cowboy Hat

    This straw cowboy hat is giving rodeo queen meets boho babe—lightweight, breezy, and made for your next sun-soaked photo dump.

    Fit & Features

    • Straw material
    • Woven design
    • Structured top
    • Wide curved brim
    • Thin twisted band, tie-back design

    Style Number/Barcode: 07302-000070

    Category Name: Vacation Dresses & Outfits

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Read All About It Newspaper Bodycon Mini Dress

    Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.

    Fit & Features

    • Newspaper print, knit fabric with stretchy lining
    • Adjustable spaghetti straps
    • Sweetheart neckline with lace trim
    • Back zipper and hook-eye closure
    • Built-in padded underwire bust
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5578

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool It Tie Front Crochet Vest

    Add a stylish twist to your look with this crochet vest. Featuring a delicate crochet pattern and a flattering tie-front closure, this vest offers both comfort and charm.

    Fit & Features

    • Crochet knit sheer fabric
    • Tie front closure design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000016

    Category Name: Vacation Dresses & Outfits

    Price: $19.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Pretty Blooms Floral Strapless Jumpsuit

    Soft, flowy, and effortlessly pretty—this strapless jumpsuit feels like your fave playlist on repeat. Wide-leg fit keeps it relaxed while the floral moment brings the charm to your vacay or weekend plans!

    Fit & Features

    • Floral print, soft and smooth knit fabric, moderate stretch
    • Strapless neckline
    • Fitted bodice
    • Flowy wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000038

    Category Name: Vacation Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Smooth Talker Lace Bow Pleated Ponte Mini Dress

    Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.

    Fit & Features

    • Smooth pointe knit fabric, minimal stretch
    • Lace bow trim square neckline
    • Spaghetti straps
    • Fitted silhouette
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3661

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Of Mine Four Piece Bracelet Set

    Perfect for stacking or styling alone, this four piece bracelet set will add a chic finishing touch to any look. This versatile bracelet set features an array of complementary styles, some adorned with dazzling rhinestones and elegant faux pearls.

    Fit & Features

    • Four-piece bracelet set
    • One faux pearl bracelet, stretchy fit
    • One twisted chain bracelet, lobster clasp closure
    • One rhinestone embellished bracelet, toggle closure
    • One chain coin charm bracelet, lobster clasp closure

    Style Number/Barcode: 07003-000035

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sensational Match Ruffle Mini Skort

    Make a sensational impression in this ruffled mini skort on vacay or brunch! Pair with the matching top to complete the cute look.

    Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

    Fit & Features

    • Smooth stretchy knit fabric
    • Mid-rise waist
    • Tiered ruffled design
    • Mini-length overlay
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000088

    Category Name: Vacation Dresses & Outfits

    Price: $26.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress

    Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.

    Fit & Features

    • Floral tie-dye print, smooth knit fabric, moderate stretch
    • Strapless neckline
    • Lace-up back design
    • Form-hugging fit
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3277

    Category Name: Vacation Dresses & Outfits

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glimmer Game Strong Layered Belly Chain

    Double the chains, double the compliments. This layered belly chain is all about sparkle with a flirty twist—perfect for beach days, rooftop nights, and every crop top moment in between.

    Fit & Features

    • Dainty textured chain, high-shine finish
    • Two-row layered design
    • Hanging diamond-shaped charms, stone embellishments
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07002-000097

    Category Name: Vacation Dresses & Outfits

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS