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.

  • Pop The Cork Platform Heels

    The perfect platform block heels for daytime celebrations! These shoes are designed to elevate your look with sleek faux leather straps and cork material for a unique style.

    Fit & Features

    • Block heel
    • Almond toe
    • Faux leather toe and adjustable ankle strap, buckle closure
    • Platform sole
    • Cork material
    • Runs true to size

    Style Number/Barcode: 07401-5283

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Undeniable Halter V-Neck Crop Top

    All you need is your undeniable sass and this crop top for an adorable style! It features a sultry halter V-neckline and a fitted pointed crop hem that flatters your figure on mineral wash stretchy rib knit fabric. Complete the look in jeans and sandals.

    Fit & Features

    • Mineral wash stretchy rib knit fabric
    • Halter V-neckline
    • Pointed crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1880

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eyes On You Lace-Up Slit Maxi Dress

    Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!

    Fit & Features

    • Gauze linen-blend woven fabric, stretchy knit lining
    • Halter neckline, spaghetti strap ties
    • Lace-up back
    • Cutout accents
    • High front slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000053

    Category Name: Vacation Looks

    Price: $48.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress

    Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Sweetheart neckline
    • Adjustable bust drawstring, cutout
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5430

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Twist Cutout Knit Midi Dress

    Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Knit fabric, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • Twist back cutout
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1950

    Category Name: Vacation Looks

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Power Moves Button Woven Vest

    Make power moves and take your style to a polished level in this button-up woven vest. Pair with the matching bottoms to complete the look.

    Fit & Features

    • Woven fabric, sewn-in woven lining
    • Button-up front closures
    • Stretchy smocked back
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Bottoms: Power Moves High-Rise Trouser Pants

    Style Number/Barcode: 06204-2104

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY, LIGHT, BLUE

    Available Size: S, M, L, XS

    Product Badge:
    • Part of a Set
  • Artsy Scene Mock Neck Abstract Mini Dress

    Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5630

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Legendary Style Western Buckle Faux Leather Sandals

    It's impossible not to make an iconic fashion statement in these faux leather sandals! Featuring a sleek square toe, a flat sole, and a Western-inspired buckle along the strap for added flair. Complete the look with a trendy denim jacket.

    Fit & Features

    • Square toe
    • Flat sole
    • Western-inspired buckle on strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1239

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Sheer Woven Palazzo Pants

    These beachy sheer woven palazzo pants feature an adjustable tie-front drawstring and a wide-leg silhouette for a relaxed fit. Style as a cover-up over your fave bikini!

    Fit & Features

    • Sheer textured woven fabric, minimal stretch
    • High-rise elasticized waist
    • Adjustable tie-front drawstring
    • Wide-leg silhouette
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06302-000003

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun-Kissed Cutie Halter Plunge Flowy Romper

    Turn heads in this romper at backyard BBQs and parties! This romper boasts a sultry plunge halter neckline, a trendy flowy silhouette that moves beautifully with every step, creating an effortlessly chic look.

    Fit & Features

    • Swiss dot woven fabric, woven shorts lining
    • Plunge halter neckline, dual spaghetti strap tie
    • Stretchy smocked waist
    • Flowy hem
    • Runs true to size

    Style Number/Barcode: 06303-000020

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: WHITE, RED

    Available Size: S, M, L, XS

  • Girlycore Off-The-Shoulder Ruffled Skater Dress

    Embrace a girly-core coquette aesthetic in this skater dress perfect for sunny days! The sweetheart neckline and cutout waist add a flirty touch, while the stretchy smocked bodice hugs your curves, and the ruffled tier short-length hem adds a feminine flair. Complete the look in wedge sandals.

    Fit & Features

    • Airy woven fabric with lining
    • Stretchy smocked bodice with bust tie
    • Cutout waist
    • Ruffled tier skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3054

    Category Name: Vacation Looks

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Prep & Sass Bubble Mini Skirt

    This skirt said “main character energy” and meant it. With a playful bubble mini hem and classic pinstripe print, she’s made for casual hangs, day dates, and being the moment.

    Fit & Features

    • Pinstriped print, cotton woven fabric, sewn-in woven lining
    • High-rise waist
    • Side zipper and hook-eye closure
    • Flouncy bubble mini hem
    • Runs true to size

    Style Number/Barcode: 06301-000005

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

  • Cherry On Top Lace Trim V-Neck Mesh Mini Dress

    This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

    Fit & Features

    • Cherry print, mesh fabric, stretchy knit lining
    • Lace trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5798

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Up Abstract Print Cutout Mini Dress

    Step up your night-out vibe in this bold abstract print mini dress designed with a plunging halter neck, open back, and sultry waist cutouts. The bodycon fit will flaunt your gorgeous curves.

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, high stretch
    • Abstract print
    • Sleeveless plunging V-neckline, tie-back halter straps
    • Textured metal accent, side cutouts, waist keyhole cutout
    • Open back, tie-back spaghetti straps, lower back ruching
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000104

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, L, XL

  • Pick Me Halter Floral Eyelet Crop Top

    Pick this floral crop top for the sweetest look! This halter crop top features a flattering V-neckline with a spaghetti strap tie for a perfect fit, while a sweet bow detail adds a touch of charm. The fitted crop hem and floral printed eyelet fabric give off a playful, summertime vibe. Complete the look in high-rise jeans for any casual plans!

    Fit & Features

    • Floral printed eyelet fabric, minimal stretch
    • Halter V-neckline, spaghetti strap tie
    • Bow along the bust
    • Fitted crop length
    • Runs true to size

    Style Number/Barcode: 06001-5365

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Highly Favored Triangle Rhinestone Lariat Necklace

    This lariat necklace will be highly favored over the rest! It features a dainty chain adorned with rhinestone charms leading to a sleek triangle charm with rhinestone trim and a single fringe chain with a rhinestone. Complete the look in a sultry cocktail dress for a rehearsal dinner or reception!

    Fit & Features

    • Dainy chain lariat necklace
    • Rhinestone charms
    • Triangle charm with rhinestone trim
    • Single fringe chain with rhinestone
    • Lobster clasp closure

    Style Number/Barcode: 07002-1872

    Category Name: Vacation Looks

    Price: $2.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Edgy Girlie Mid-Rise Studded Denim Skort

    Modern and edgy, this mid-rise denim skort brings the cool factor to your concert or going-out look! Let the studded pocket trim add a touch of daring to your outfit, while the bodycon fit flatters along the mini-length.

    Fit & Features

    • Denim fabric, non-stretch
    • Mid-rise waist
    • Bodycon fit, mini-length skirt overlay
    • Shorts lining
    • Studded pocket trim on the front, back pockets
    • Front button and hidden zipper closure, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000029

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L, XL

  • Confident Flirty Strappy One-Shoulder Crop Top

    Make your crush stop and stare at you in this sleeveless crop top! It boasts a flirty strappy one-shoulder neckline, and a fitted crop hem, and is made from a stretchy rib knit fabric. Complete the look in a denim mini skirt for any casual plans!

    Fit & Features

    • Stretchy rib knit fabric
    • Strappy one-shoulder neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1878

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brunch At Noon Off-The-Shoulder Floral Romper

    Step out for brunch in this floral off-the-shoulder romper with a flirty tie-waist and ruffled hem for a playful look.

    Fit & Features

    • Floral print, chiffon fabric, woven shorts lining
    • Off-the-shoulder neckline, ruffled short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Tie-waist
    • Flowy ruffled short hem
    • Runs true to size

    Style Number/Barcode: 06403-1093

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BLUSH

    Available Size: S, M, L

  • 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 Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold And Breezy Door Knocker Earrings

    These intertwined door knocker earrings are the perfect mix of bold and breezy, ready to elevate your weekend ‘fit or vacay vibe.

    Fit & Features

    • Metal material
    • Round door knocker silhouette
    • Linked double-ring design
    • Intertwined wrapped fabric detailing
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000035

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • 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 Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale