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.

  • Sea Worthy Shell Charm Hoop Earrings

    From pool parties to beach bashes, these shell charm hoop earrings bring all the summery vibes! Complete the look with cute sandals.

    Fit & Features

    • Hoop earrings
    • Paperclip chain-link design
    • Shell charms
    • Hook closure, rubber stopper

     

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

    Style Number/Barcode: 07001-2014

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set For Cuteness Twist Back Slit Rib Knit Maxi Dress

    You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Shoulder straps
    • Twist back design
    • High side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5577

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Down For Anything Buckle Criss-Cross Sandals

    With these trendy buckle criss-cross sandals you'll be down for any last minute plans that involve showing them off!

    Fit & Features

    • Square toe
    • Buckle criss-cross straps
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1259

    Category Name: Vacation Looks

    Price: $8.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Girl On The Go Square Sunglasses

    Made for the girl on the go. These square-frame sunglasses bring effortless cool to every outfit, whether you're brunch-bound or dodging exes at the beach party.

    Fit & Features

    • Square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000047

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • Life's A Breeze Floral Cutout Midi Dress

    This floral cutout maxi dress makes getting ready a breeze! It features short puff sleeves, a ruched sweetheart bodice with a flirty waist cutout that leads to a flowy, maxi silhouette with a slit accent. Composed of a chiffon-lined fabric with no stretch. Style with a trendy mini tote.

    Fit & Features

    • Short puff sleeves
    • Ruched sweetheart bust
    • Waist cutout, smocked back
    • Maxi silhouette with slit accent
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-3193

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Vacay Strapless Tube Crop Top

    Get ready for vacay packing this tube top for endless fun under the sun! Whether you're island hopping in Greece or sipping a mai tai on the beach, this crop top will keep you so trendy. It boasts a strapless neckline with a non-slip grip lining for a secure fit, a stretchy smocked back for easy on-and-off styling, plus a cinched front that adds a flirty touch. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Endless Vacay High Rise Wide-Leg Trouser Pants

    Fit & Features

    • Texture woven fabric, partial sewn-in knit lining
    • Stretchy smocked back
    • Non-slip grip lining
    • Cinched front
    • Ultra-cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2528

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glow Getter Strapless Cutout Mini Dress

    Catch flights and compliments. This strapless mini hugs you in all the right places with a ruched bust ring detail and cheeky cutout that turns the charm up. Brunch, beach, or bae date—it’s a serve every time.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless sweetheart tube neckline with hardware trim
    • Cutout accent
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000033

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Destined For Sun Tropical Mesh Mini Skirt

    This tropical mesh mini skirt is destined to go with you on the next sunny getaway! Featuring a high-rise waist, a bodycon silhouette with a wrap accent to highlight your curves and a mini-length hem. Complete the look with the matching top.

    Shop The Matching Top: Destined For Sun Tropical Mesh Tie Front Top

    Fit & Features

    • Tropical palm print, sheer mesh fabric, moderate stretch
    • Long sleeves with cuffs
    • Tie-front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06501-0979

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Go Jacquard Woven Tote Bag

    Grab your essentials and you'll be ready for any plans with this jacquard woven tote bag! Perfect for vacation, beach days, or daytime outings, this tote bag features top handles and a spacious interior with a zipper pocket and two slot pockets convenient for your cash, cards, keys, and phone. Complete the look with sunglasses and sandals!

    Fit & Features

    • Top handles
    • Spacious interior, zipper pocket, two slot pockets
    • Jacquard woven material

    Style Number/Barcode: 07203-2024

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Aloha Babe Flower Graphic Crop Tee

    Whether you're on vacay or just hanging out, this flower graphic crop tee adds a cute look to your favorite bottoms.

    Fit & Features

    • Cotton knit stretchy fabric
    • Short sleeves
    • Crew neckline
    • Flower graphic
    • Relaxed fit
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000051

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L/XL

  • Trend Factor Angled Oval Sunglasses

    Level up the trend factor of your summer looks with these cool shades. The sunglasses feature an angled oval-shaped design with a translucent plastic frame, built-in nose pads, and tinted lenses. Pair with a charm necklace and sneakers.

    Fit & Features

    • Angled oval-shaped design
    • Translucent plastic frame
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1088

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Day Bestie Crop Tube Top

    Sunshine days call for a bestie like this cropped tube top! It's designed with a trendy decor insert and a fitted silhouette that flaunts your figure.

    Fit & Features

    • Smooth, stretchy knit fabric
    • Strapless neckline, decor insert
    • Fitted silhouette
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000058

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, BLACK

    Available Size: L, XS, S, M

    Product Badge:
    • Sale
  • Wifey Material Scoop Neck Tank Crop Top

    From the bachelorette bash to the big day, this tank crop top will channel those wife vibes! The top boasts a flattering scoop neckline and shoulder straps, a front embroidery with the words, "Wifey Material", and a flirty fitted crop hem on rib knit fabric. Complete the look in a white mini skirt and sneakers!

    Fit & Features

    • Rib knit fabric, minimal stretch
    • Scoop neckline
    • Shoulder straps
    • front embroidery with the words, "Wifey Material"
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1846

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Butterfly Baby Layered Chain Belt

    Upgrade your style with this butterfly layered chain belt! This trendy belt features layered chains and adorable butterfly charms for a fun and playful look and a secure lobster clasp closure. Complete the look in a basic bodycon midi dress and heels for a concert or dinner out with the girls!

    Fit & Features

    • Layered chain design
    • Butterfly charms
    • Lobster clasp closure

    Style Number/Barcode: 07301-0710

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Oasis Ruffle Mini Skirt

    Escape to a sunny destination with this alluring high-rise ruffle mini skirt! Pair with the matching top to complete the trendy vibe.

    Fit & Features

    • Slinky knit stretchy fabric
    • High-rise waist
    • Bodycon silhouette
    • Side ruched seams
    • Ruffled mini-length hem
    • Runs true to size

     

    Shop The Matching Top: Sunny Oasis Halter Crop Top

    Style Number/Barcode: 06501-000053

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Classic Chic Woven Cabby Hat

    Elevate your casual 'fits with this lightweight woven cabby hat! It features a classic cabby design with a short curved brim and side button accents. Includes adjustable ties hidden on the inside for a tighter fit. Style with ankle booties for a chic vibe.

    Fit & Features

    • Woven fabric
    • Classic cabby design
    • Short curved brim
    • Side buttons
    • Adjustable ties for tighter fit

    Style Number/Barcode: 07302-1623

    Category Name: Vacation Looks

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • By The Beach V-Neck Halter Babydoll Crop Top

    Enjoy a sunny day by the beach in this breezy babydoll crop top with a pretty eyelet V-neckline and a flowy silhouette. Perfect for styling as a cover-up or by itself.

    Fit & Features

    • Cotton woven fabric
    • Adjustable spaghetti straps
    • V-neckline, eyelet bust
    • Stretchy smocked back panel
    • Flowy uneven crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2763

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Festive Fun Strapless Striped Bandeau Crop Top

    Weekend activities just got a little cuter in this striped bandeau crop top perfect for vacations or going to a summer fair! The strapless sweetheart neckline and tie front bust create a comfortable and flattering fit, while the ultra-cropped hem and striped print bring a stylish touch. Complete the look with the matching bottoms.

    Shop The Matching Bottoms: Festive Fun High-Rise Striped Palazzo Pants

    Fit & Features

    • Striped print, woven lined fabric
    • Strapless sweetheart neckline
    • Stretchy smocked back
    • Tie front bust design
    • Padded bra cups
    • Ultra-cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2561

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sweet Tie-Strap Eyelet Mini Dress

    Keep your summer date outfit sweet with the cutest eyelet mini dress! Designed with a lightweight eyelet knit fabric, this adorable short dress will bring the charm. It features a sleeveless square neckline with ruching at the bust, tie-shoulder straps, and a bodycon silhouette with a mini-length hem to flaunt your figure. Style with sneakers for a casual look or mules for a dressier vibe!

    Fit & Features

    • Sheer eyelet knit fabric with knit lining
    • Moderate stretch
    • Ruched square neckline
    • Tie-shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5452

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    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 Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: L, XL

  • Looking Good Sweetheart Tie Front Crop Top

    Looking good will be effortless in this crop top perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, this top offers comfort and a flattering silhouette. The sweetheart neckline and cropped hem will flatter your figure, while the tie-front adds a touch of flare to your outfit. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Looking Good V-Waist Smocked Flare Pants

    Fit & Features

    • Stretchy smocked knit fabric
    • Spaghetti straps
    • Sweetheart neckline
    • Tie-front 
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5225

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Fly Butterfly Chain Belt

    Look fly in this adorable butterfly chain belt! Complete the look in a bodycon midi dress and sandals.

    Fit & Features

    • Butterfly chain belt
    • Lobster clasp closure

    Style Number/Barcode: 07301-1159

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed and Stunned Halter Striped Maxi Dress

    This striped knit maxi brings the heat with a flirty open back, high front slit, and sheer vibes made for beach strolls or rooftop sips.

    Fit & Features

    • Striped texture knit design, sheer fabric
    • Halter plunge neckline, tie straps
    • Open back with tie strap
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000137

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Beauty Mesh Strapless Corset Mini Dress

    Showcase your beauty at spring and summer parties in this strapless corset mini dress! Designed with a lightweight sheer mesh fabric with a lining for coverage, the dress offers an airy, effortlessly chic vibe. It features a strapless straight-across neckline, a corset-style bodice for a snatched silhouette, and an asymmetric mini-length hem with a flowy A-line fit you'll love. Style with hoop earrings and a layered necklace.

    Fit & Features

    • Sheer mesh fabric, knit lining, stretchy
    • Strapless straight neckline
    • Corset flexible boning bodice, back zipper hook-eye closure
    • Asymmetric hem
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3337

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale