Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Trendy Fab Zip-Front Denim Romper

    Trendy fab will be your vibe in this cool-girl denim romper featuring a collared neckline, zip-front design, and form-hugging fit!

    Fit & Features

    • Denim fabric, minimal stretch
    • Sleeveless collared neckline
    • Zip-front V-neckline
    • High-rise waist, belt loops
    • Single front pocket
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0481

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: MEDIUM, DENIM

    Available Size: S, L

    Product Badge:
    • Back In Stock
  • Sweet Charm Lace-Up Babydoll Crop Top

    You'll radiate sweet charm in this babydoll crop top all season! With delicate spaghetti straps and a V-neckline, this top boasts a stretchy smocked bust that hugs your curves for a flattering fit. The lace-up back adds a touch of allure, while the ruffled cropped hem adds a playful touch. Complete the look in a denim skirt and block heels for any occasion!

    Fit & Features

    • Gauze woven fabric, no stretch
    • V-neckline
    • Stretchy smocked bust
    • Spagehtti straps, lace-up back
    • Babydoll silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 06003-2524

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Flower Strap Stiletto Mules

    You'll be ready for your next vacay in these fab faux leather mules featuring a thin strappy design with a bold flower accent and short stiletto heel.

    Fit & Features

    • Stiletto heel
    • Faux leather material
    • Open almond-shaped toe
    • Thin strappy design, flower accent
    • Open back, on-and-off styling
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000085

    Category Name: Vacation Looks

    Price: $30.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Refreshing Charm Smocked Striped A-Line Mini Dress

    This sleeveless striped mini dress features a flattering square neckline and a smocked A-line silhouette with a trendy drop waist seam. The ruffled hem adds a flirty touch perfect for picnics or a day at the beach. 

    Fit & Features

    • Striped woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Smocked A-line silhouette
    • Drop waist seam
    • Mini-length ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5826

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Life Beaded Straw Cowboy Hat

    A straw cowboy hat featuring a distressed wide brim with a beaded string trim and a snug fit. Style with cowboy boots.

    Fit & Features

    • Distressed wide brim
    • Beaded string trim
    • Snug fit
    • Straw material

    Style Number/Barcode: 07302-1702

    Category Name: Vacation Looks

    Price: $4.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Cutie Halter Cutout Striped Linen Jumpsuit

    Hit the coast in this breezy cute striped linen jumpsuit! This playful piece features a halter neckline with a spaghetti strap tie and a cutout bodice to flaunt some skin. The stretchy smocked back and wide-leg silhouette provide comfort and style, while the striped print adds a pop of personality to the linen-blend fabric. Complete the look in platform sandals.

    Fit & Features

    • Striped print, linen blend fabric
    • Halter neckline, spaghetti strap tie
    • Cutout bodice
    • Back zipper and hook-eye closure, stretchy smocking
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0817

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Catch High Rise Slit Midi Skirt

    Catch this stylish midi skirt for the ultimate vacation look! Featuring a high-rise elasticized waist and a flattering bodycon silhouette with a sultry side slit along the midi-length hem. Complete the look with the matching top.

    Shop Matching Top: Stylish Catch Tie Front Knit Bandeau

    Fit & Features

    • Knit fabric, sewn-in knit lining, minimal stretch
    • High-rise elasticized waistband
    • Bodycon fit
    • Side slit
    • Midi-length
    • Runs true to size

    Style Number/Barcode: 06401-0655

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Focus Strapless Rib Knit Tube Crop Top

    Attract all the attention when you're in this flirty tube crop top all summer long! Featuring a strapless neckline and a form-hugging fit, this top will accentuate your figure in all the right ways. The hanky-cropped hem adds a playful touch to the rib knit fabric. Complete the look in a denim skort.

    Fit & Features

    • Rib-knit stretchy fabric
    • Strapless neckline
    • Hanky cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1884

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Follow The Sun Lace-Up Tropical Midi Dress

    Follow the sun to your next destination in this tropical midi dress! This bodycon dress flatters your figure with a square neckline, spaghetti straps, and a lace-up back. The side ruched seam and slit add a touch of chic to the midi-length hem. Complete the look in sunglasses and sandals!

    Fit & Features

    • Tropical print, stretchy knit fabric, bust lining
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5745

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clueless Vibes Denim Belted Mini Skirt

    Serving throwback prep with a spicy upgrade. This denim houndstooth mini skirt brings the drama with a statement belt and a mini silhouette made to steal glances.

    Fit & Features

    • Houndstooth pattern, denim cotton-blend fabric, no stretch
    • Mid-rise belted waist
    • Bodycon mini-length silhouette
    • Front button and hidden zipper closure
    • Back pockets, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06601-000007

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Cutest Bloom Strapless Floral Smocked Tube Top

    Bare your shoulders in this cute strapless floral tube top this summer! Made from floral-printed eyelet fabric, this top adds a touch of charm to any outfit. The strapless neckline and fitted crop hem flatter your figure, while the stretchy smocked bodice ensures a comfortable fit. Complete the look in a trendy skirt for any occasion!

    Fit & Features

    • Floral printed eyelet fabric, stretchy knit lining
    • Strapless neckline
    • Stretchy smocked bodice
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5366

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • No You Hang Up Tube Mini Dress

    Get ready to wow in this tube mini dress for your next date! This dress is designed with an alluring twist bust with a keyhole cutout that shows some skin, while the form-hugging A-line silhouette accentuates your curves.

    Fit & Features

    • Texture knit stretchy fabric
    • Strapless tube sweetheart neckline
    • Twist bust, keyhole cutout
    • Form-hugging, A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000018

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Style Button Ruffled Striped Linen Skater Dress

    Catch everyone's attention with your cute style in this striped skater dress perfect for casual summer plans!  Made with striped linen fabric, this dress is perfect for any occasion. Featuring a scoop neckline with a bust tie and adjustable spaghetti straps, this dress is both stylish and comfortable. The button down front and ruffled trim add a fun touch, while the skater silhouette and short-length hem create a flattering look. Complete the look with hoop earrings and trendy sandals.

    Fit & Features

    • Striped print linen-blend fabric lined with woven, no stretch
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Button down front and ruffle trim
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5731

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Slay Halter Cowl Neck Ribbed Knit Maxi Dress

    This sleek halter cowl neck maxi dress is a simple chic style that will make your casual outfits slay! Made with a lightweight stretchy ribbed knit fabric, it features a sleeveless draped cowl neckline with tie-back halter spaghetti straps, an alluring open back with a lower tie-back strap, and a form-hugging maxi-length silhouette to flaunt your stunning figure. Pair with slip-on sandals for a relaxing weekend getaway.

    Fit & Features

    • Stretchy ribbed knit fabric, partial front knit lining
    • Cowl neckline, halter spaghetti straps
    • Open back, tie-back strap
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5685

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Day Puff Sleeve Cut Out Denim Romper

    Indulge in the dreamy vibes of this denim romper for casual bridal showers, birthdays, or graduation parties! The V-neckline and cutout sides add a touch of allure, while the form-hugging fit accentuates your curves. Made from soft denim fabric, the short-length hem offers a flirty and comfortable style. Complete the in wedge sandals.

    Fit & Features

    • Denim fabric, minimal stretch
    • Back zipper and hook-eye closure
    • Cutout sides
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0372

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romantic Effect Halter Tie Back Floral Satin Top

    Indulge in the ultimate romantic effect in this halter tie-back floral satin top! Featuring a flattering V-neckline and delicate halter spaghetti straps, this top turns heads with its open tie-back closure. The fitted pointed hem and beautiful floral design on luxurious satin fabric make it a must-have for your wardrobe. Complete the look in high-rise jeans and mules.

    Fit & Features

    • Floral design, satin woven fabric
    • Spaghetti straps
    • Open tie-back closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2382

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemain Charm Halter Open Back Tie Dye Maxi Dress

    Meet the bohemian charm of this tie dye maxi dress for summer soirees and parties! Featuring a halter cowl neckline and an alluring open back with tie closure, this dress exudes sensuality. The side ruched seams and form-hugging fit accentuate your curves, while the front slit and sheer maxi-length hem add a chic touch! Complete the look with earrings and a clutch.

    Fit & Features

    • Tie dye print, stretchy mesh fabric, sewn-in knit lining
    • Halter cowl neckline
    • Open back with tie closure
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3445

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripes of The Day Tie Side Romper

    Show your stripes of the day on this trendy romper! It features a sleeveless, v-neck, adjustable spaghetti straps, surplice bodice, and an elasticized waist with side tie detail. Complete the look in chunky heels for the perf summer vibe.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Surplice bodice
    • Elasticized waist, side tie detail
    • Striped print
    • Woven lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06403-0182

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Appeal One-Shoulder Bodycon Mini Dress

    This one-shoulder mini dress features a unique asymmetrical neckline and is made from super soft, stretchy knit material. The bodycon silhouette perfectly highlights your curves for date nights or parties. 

    Fit & Features

    • Soft, stretchy knit material
    • One-shoulder neckline
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3553

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get The Look Crochet High-Rise Pants

    Curate effortless vibes in these crochet high-rise pants, perfect for pairing with the matching top for a cute look!

    Fit & Features

    • Embroidered crochet fabric, sewn-in panty knit lining
    • High-rise waist, side zipper and hook-eye closure
    • Sheer design
    • Runs true to size

    Shop The Matching Top: Get The Look Crochet Halter Crop Top

    Style Number/Barcode: 06402-000005

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: M

    Product Badge:
    • Part of a Set
  • Babe In Stripes Strapless Cutout Ribbed Knit Midi Dress

    Be a bold babe in this striped knit midi dress perfect for styling over your swimsuit or wearing alone. Featuring a strapless neckline and cutout bodice, this bodycon dress will hug your curves in all the right places. The stretchy ribbed knit fabric and midi-length hem add comfort and style, while the striped pattern adds a fun twist. Complete the look with sandals and sunnies!

    Fit & Features

    • Striped pattern
    • Stretchy ribbed knit fabric
    • Strapless neckline
    • Cutout bodice
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1939

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Enchanting A-Line Floral Chiffon Midi Dress

    Have everyone under your spell in this floral chiffon midi dress as a stunning wedding guest or to attend a garden party! Featuring a square neckline with a bust tie, elasticized shoulder straps, and an A-line silhouette, this dress flatters any figure. The front slit and midi-length hem add a touch of sophistication. Complete the look in block heels and earrings!

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Elasticized shoulder straps
    • Square neckline, bust tie
    • Back zipper and hook-eye closure
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3304

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Bow Print Canvas Tote Bag

    Carry your essentials in this sweet canvas tote bag. This charming tote features an eye-catching bow print design that adds a touch of feminine flair to any outfit and a spacious interior for your everyday essentials!

    Fit & Features

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

    Style Number/Barcode: 07203-000025

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free