Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • 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 Looks

    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 Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Femme Charm Halter Eyelet Corset Top

    Add a touch of femme charm with this eyelet corset top, perfect for sunny-day styling. The top boasts a flirty plunge halter neckline and a cropped hem that flatters your figure.

    Fit & Features

    • Eyelet fabric, woven lining
    • Halter plunge neckline, elasticized strap
    • Multiple back hook and eye fasteners
    • Flexible boning, crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000008

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • 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 Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced in Daydreams Satin Halter Floral Mini Dress

    This floral satin halter mini dress is sweet, flirty, and made for RSVP-ing yes, complete with dreamy lace details and a flattering A-line silhouette.

    Fit & Features

    • Floral print, woven satin fabric, bust lining
    • Lace trim halter neckline, spaghetti strap tie
    • A-line silhouette
    • Lace trim front slit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000652

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: CORAL

    Available Size: S, M, L

  • 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 Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Attraction Toe Ring Strappy Block Heels

    A pair of strappy block heels with a trendy toe ring trim that gives every outfit a sweet look!

    Fit & Features

    • 2.5" Block heel
    • Square toe
    • Strappy design
    • Toe ring trim
    • Luxe fit cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-5260

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: TAN, WHITE, BLACK

    Available Size: 5.5, 6.5, 7, 7.5, 8.5, 10, 6, 9

  • 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 Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • About A Girl Bow Canvas Tote Bag

    Carry your essentials in style with this charming bow canvas tote bag. Perfect for shopping trips, beach days, or casual outings, this adorable tote adds a cute touch to any outfit.

    Fit & Features

    • Bow print design
    • Top handles
    • Spacious interior
    • Canvas material

    Style Number/Barcode: 07203-000032

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist Of Fate Strapless Ruffled Maxi Dress

    Because you didn’t plan to look this good... it just happened. Make your way in this breezy maxi dress designed with effortless, dreamy details from the twisted strapless bust to strappy open back and flowy ruffled silhouette. 

    Fit & Features

    • Satin woven fabric, woven lining
    • Strapless sweetheart neckline
    • Twisted bust, keyhole cutout accent
    • Strappy open back
    • Ruffled silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000168

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S

  • 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 Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Icon Basic Thong Sandals

    A picture-perfect sunny day calls for these basic thong sandals to style with your everyday look!

    Fit & Features

    • Almond toe
    • Sleek thong toe strap
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-000003

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Fun Flutter Sleeve Tie-Front Top

    This adorable tie-front top was made for weekend fun, designed with short flutter sleeves and an ultra-cropped hem. Style with the matching mini skort for the cutest vibe.

    Shop Matching Bottoms: Weekend Fun Ruffled Mini Skort

    Fit & Features

    • Cotton woven fabric with swiss dot pattern, no stretch, partial knit lining
    • V-neckline, tie-front design
    • Short flutter sleeves
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000011

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • 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 Looks

    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 Looks

    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 Looks

    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 Looks

    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 Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Frill Seeker Ruffled Denim Shorts

    These denim shorts? Total heartthrob. With a mid-rise waist and ruffled hem, it’s giving playful, pretty, and just the right amount of sass for any OOTD.

    Fit & Features

    • Cotton denim fabric, no stretch
    • Mid-rise waist
    • Side zipper and hook-eye closure
    • Ruffled trim hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 06303-000015

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: S, M, L, XL

  • 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 Looks

    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 Looks

    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 Looks

    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 Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale