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.

  • Fall Into Fashion Crew Neck Open Back Maxi Dress

    You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Strappy open back
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5654

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Tropical Knit Wide-Leg Pants

    These alluring tropical wide-leg pants will have you ready for a dreamy vacay! The stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The pants are shaped with a high-rise elasticized waistband for comfortable wear and a relaxed wide-leg silhouette for a trendy look. Style with the matching crop top and hoop earrings.

    Shop Matching Top: Vacay Ready Tropical Knit Halter Crop Top

    Fit & Features

    • Abstract tropical print
    • Stretchy knit
    • High elasticized waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2481

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Much Love Sweetheart Swiss Dot Mesh Mini Dress

    It's too easy to fall for this flirty swiss dot mesh mini dress perfect for soirees! The sweetheart neckline and padded bra cups provide a flattering fit, while the adjustable spaghetti straps and dual front ruched drawstrings allow for a customizable look. The bodycon fit and mini-length hem showcase your figure, all in a beautiful swiss dot mesh fabric. Complete the look in sandals.

    Fit & Features

    • Swiss dot mesh fabric, sewn-in knit lining, stretchy
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Padded bra cups
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3253

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Cutie Crochet Wide-Leg Pants

    Show off the cutest boho vibe in these breezy crochet wide-leg pants! Designed with an airy sheer crochet knit fabric, these pants are perfect for summer days spent by the coast. They feature a high waist, a hip-hugging fit, and a wide-leg silhouette for that effortlessly chic vibe. Complete your look with the matching crop top and a pair of strappy sandals!

    Shop Matching Top: Boho Cutie Bell Sleeve Crochet Crop Top

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • High-rise elastic banded waist
    • Hip-hugging fit
    • Wide-leg silhouette
    • Panty lining not included
    • Runs true to size

    Style Number/Barcode: 06502-2488

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Dreams Hanky Hem Floral Mini Dress

    Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.

    Fit & Features

    • Floral print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with lace trim
    • Spaghetti straps
    • Drop waist silhouette
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3462

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Express Your Style V-Neck Ruffle Bodycon Mini Dress

    Express your devotion to style in this charming sleeveless mini dress perfect for casual showers or brunch! This dress features adjustable spaghetti straps for the perfect fit, a flirty V-neckline with a bust tie for added charm, and a bodycon fit to accentuate your curves. The mini-length hem and ruffle trim throughout add a touch of romance to this head-turning dress. Complete the look with earrings.

    Fit & Features

    • Ruffle trim throughout, knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5789

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Serenity V-Neck Crochet Crop Top

    Flirty yet casual, this crochet crop top is perfect for grabbing cocktails at sunset by the beach! The delicate v-neckline and shoulder straps give a flattering silhouette, while the cropped hem adds a cute touch. Complete the look in a flowy maxi skirt and sandals.

    Fit & Features

    • Sheer crochet fabric, no stretch
    • V-neckline
    • Shoulder straps
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06005-2015

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetie Status Halter Crochet Trim Babydoll Dress

    You'll look absolutely adorable in this babydoll dress at showers, birthdays, or backyard parties! The halter neckline and cutout bodice add a touch of allure, while the crochet trim and babydoll silhouette create a delicate and feminine look along the short-length hem. Complete the look in sandals and hoop earrings.

    Fit & Features

    • Gauze woven fabric, woven lining, no stretch
    • Halter neckline with spaghetti strap ties
    • Cutout bodice
    • Crochet trim
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5421

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Profound Bloom Off-The-Shoulder Floral Skater Dress

    You'll be blossoming from all the compliments you'll get wearing this off-the-shoulder floral dress! This skater dress features a playful sweetheart neckline, a bust tie, and a ruffled short-length hem bringing plenty of sass and sweetness to your style. Complete the look with earrings and strappy sandals for any occasion!

    Fit & Features

    • Floral print, woven fabric, bust lining
    • Off-the-shoulder, sweetheart neckline
    • Padded bra cups, back zipper and hook-eye closure
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3459

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picking Flowers Halter Strappy Back Daisy Skater Dress

    This daisy print skater dress will have you dreaming of sunny days picking flowers! The halter spaghetti strap neckline perfectly frames your shoulders while the cutout bodice adds a touch of allure. The strappy open back creates a stunning statement and the skater silhouette and tiered ruffled short-length hem give you a playful and fun look. Complete the look in sandals for a brunch or day date!

    Fit & Features

    • Daisy print, woven fabric with lining, no stretch
    • Spaghetti strap
    • Strappy open back
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5794

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Beauty Sheer Crochet Coverup Top

    Layer on this breezy sheer crochet coverup top for an effortless pretty vibe! Made with a trendy open-knit crochet fabric, it features a wide boat neckline, long dolman-style sleeves, a long-length hem with high side slits for added movement, and an overall relaxed flowy fit. Pair with a basic bralette with denim shorts for the perf summer look.

    Fit & Features

    • Sheer open-knit crochet fabric, minimal stretch
    • Boat neckline
    • Long dolman sleeves
    • Long-length hem, side slits
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-1963

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Graceful Presence Sweetheart Floral Skater Dress

    Have a graceful presence in this floral skater dress at showers or graduations! A charming dress with a sweetheart neckline and tie spaghetti straps, the skater silhouette flatters your figure, while the short-length hem adds a playful touch. Complete the look in wedge sandals.

    Fit & Features

    • Floral print, woven fabric lined with stretchy knit
    • Tie spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3194

    Category Name: Vacation Dresses & Outfits

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Set Up High Rise Geometric Palazzo Pants

    Super cute and perfect for getaways or weekend plans, these palazzo pants are stylish and comfortable for anything on your calendar! They feature a flattering smocked high-rise waist, a wide-leg silhouette, and a trendy geometric print on woven fabric. Complete the look with the matching top.

    Shop The Matching Top: All Set Up Geometric Bandeau Halter Crop Top

    Fit & Features

    • Geometric print, woven fabric, no stretch
    • Smocked high-rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1420

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Getaway Puff Short Sleeve Floral Romper

    This floral romper is the perfect piece to pack for your next sunny getaway or weekend plans! With delicate puff sleeves, a flattering square neckline and bust tie, and a comfortable stretchy smocked back, this short-length romper will have you looking and feeling stunning on your next adventure. Complete the look with hoop earrings.

    Fit & Features

    • Floral print, woven fabric, stretchy knit lining
    • Puff short sleeves
    • Square neckline with bust tie
    • Stretchy smocked back
    • Short-length 
    • Runs true to size

    Style Number/Barcode: 06303-0257

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New You Sweetheart Halter Crop Top

    The new you and look has arrived with this sassy halter crop top perfect for beach days and casual hangs! The sleeveless rib knit top fits and flatters with a sweetheart neckline, halter spaghetti strap tie, cinched bust detail, and cropped hem. Complete the look in denim shorts and shades!

    Fit & Features

    • Stretchy rib knit fabric
    • Sweetheart neckline
    • Spaghetti strap tie
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-1935

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jet-Set to Paradise Strappy Cutout Tropical Knit Jumpsuit

    This alluring tropical knit jumpsuit will have you ready to jet-set to paradise! The stretchy knit fabric showcases a contrasting tropical palm leaf print for a dreamy vacay vibe. The jumpsuit is shaped with a sleeveless strappy halter neckline with a cross-front cutout design and a sultry waist cutout. The halter straps lead to an open strappy lattice back design with a tie closure to find your perfect fit. Front ruching at the waist offers a flattering look, leading to a relaxed wide-leg silhouette. Complete your look with espadrille sandals.

    Fit & Features

    • Tropical printed stretchy knit fabric
    • Sleeveless strappy halter neckline
    • Cross-front cutout design, waist cutout
    • Open strappy lattice back design, tie closure
    • Ruched waist
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-2456

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Cutie Bell Sleeve Crochet Crop Top

    Show off the cutest boho vibe in this breezy crochet crop top! Designed with an airy sheer crochet knit fabric, this top is perfect for summer days spent by the coast. It features a wide scoop neckline, long bell sleeves with a stylish flare, a tie-back design at the neck, and a cropped hem with a form-hugging fit. Complete your look with the matching wide-leg pants and a pair of strappy sandals!

    Shop Matching Bottoms: Boho Cutie Crochet Wide-Leg Pants

    Fit & Features

    • Sheer crochet knit fabric, minimal stretch
    • Scoop neckline
    • Long bell sleeves
    • Tie-back design
    • Fitted cropped hem
    • Bra lining not included
    • Runs true to size

    Style Number/Barcode: 06005-1951

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fluttering Elegance Rhinestone Butterfly Earrings

    Create a statement in these elegantly whimsical earrings! Featuring a top rhinestone post with cascading dainty chain links with rhinestone embellished butterfly charms. Complete the look with a ring set for any occasion!

    Fit & Features

    • Top rhinestone post
    • Cascading dainty two-row chain-link design
    • Rhinestone embellished butterfly charms
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2056

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Perfectly Comforting Tie Front Longline Duster

    A longline duster features trendy flared long sleeves and dual tie-front design and is made from a soft and stretchy rib knit fabric making it perfect for layering. 

    Fit & Features

    • Rib knit soft and stretchy material
    • Flared long sleeves
    • Dual tie-front design
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06202-0488

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Spotlight Strapless Ruched Corset Top

    You'll be the center of attention in this corset top everywhere you go! Made from a ruched woven fabric, this corset top sets the bar high with a strapless neckline, flexible boning, and a cropped hem to flaunt your figure. Plus, the hidden back hook and eye fasteners secure the style. Complete the look in cute jeans for any plans!

    Fit & Features

    • Ruched woven fabric
    • Strapless neckline
    • Hidden back hook and eye fasteners
    • Flexible boning
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2296

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ultimate Chic Choice Floral Tie-Back Short Dress

    For the ultimate chic choice, pick this floral short dress for all your summer plans! The sweetheart neckline and spaghetti straps give a flirty touch, while the dual tie-back design ensures a perfect fit. The underwire bust and flexible boning offer support and structure, with a short-length hem for a stunning silhouette. Complete the look with dainty chic earrings.

    Fit & Features

    • Ditsy floral print, woven fabric lined with stretchy knit
    • Sweetheart neckline, underwire bust
    • Spaghetti straps
    • Dual tie-back design
    • Flexible boning
    • Short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3447

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mentionable Flirt One-Shoulder Asymmetrical Crop Top

    For an effortless flirty outfit, pair this one-shoulder crop top with a trendy pair of denim! It features a single shoulder strap, an adjustable side drawstring to let you customize the fit, and an asymmetrical cropped hem on soft knit fabric. Complete the look in a denim midi skirt and sneakers.

    Fit & Features

    • Soft knit stretchy fabric, bust lining
    • One-shoulder neckline
    • Side adjustable drawstring
    • Asymmetrical cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1860

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Casual Everyday Ribbed Knit Midi Dress

    This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-4934

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Splendor A-Line Faux Pearl Lace Mini Dress

    Look and feel gorgeous in this lace A-line mini dress at parties and showers! This playful mini dress features a flattering V-neckline, spaghetti straps, and a lace-up back for the perfect fit. The A-line silhouette and faux pearl embellishments add a touch of whimsy to this lacey ensemble! Complete the look in block heels and a clutch.

    Fit & Features

    • Faux pearl embellishments
    • Lace fabric lined with stretchy knit
    • Spagehtti straps
    • V-neckline
    • Lace-up back, zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3018

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale