Vacation Looks

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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.

  • It's The Tequila Talking Graphic Tee

    Live your best life with this fun graphic tee that says it all! It features a crew neckline, short sleeves, a center script that reads "It's The Tequila Talking," and a cropped fit with a cute knot-front detail. Complete the look with distressed denim and hoop earrings.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Script that reads "It's The Tequila Talking"
    • Cropped, form-hugging fit
    • Knot-front detail
    • Jersey knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1095

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Romance Sleeveless Lace-Up A-Line Midi Dress

    Designed for a modern-day romance, this sleeveless woven midi dress is perfect for day dates! The sweetheart ruched neckline and adjustable straps are flattering, while the lace-up design cinches your waist for a beautiful silhouette. The front slit adds a touch of allure to this A-line midi-length dress. Complete the look in strappy wedges.

    Fit & Features

    • Texture woven fabrication with a woven lining
    • Sweetheart neckline, ruched bust, dainty lace trim
    • Adjustable straps
    • Lace-up waist, stretchy smocked back
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5722

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dressing For Sunshine Eyelet Lace Mini Dress

    The perfect eyelet lace mini dress for sunny days! It features adorable puff short sleeves, a sweetheart neckline, a front bust ruched drawstring, and a bodycon silhouette. The eyelet lace fabric includes a knit lining and offers moderate stretch. Complete the look in this mini dress with cute sandals.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neckline
    • Front bust ruched drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5118

    Category Name: Vacation Looks

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twice The Love Rib Knit Midi Skirt

    Dive into cozy rib knit love with this midi skirt! Perfect for everyday styling, this midi skirt features a high-rise elasticized waist and curve-flaunting bodycon silhouette and a side slit that shows some skin. Complete the look with the matching top.

    Shop Matching Top: Twice The Love Rib Knit Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0937

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Shell-Trim Straw Cowboy Hat

    Capture the coastal cowgirl trend with this shell-trim cowboy hat perfect for breezy days by the water! Crafted with a woven straw material, it features a structured top, a wide brim with curved sides, and a seashell-beaded accent trim and long neck strap for those beachy vibes. Includes an interior elastic band. Style with a crochet top and jean shorts.

    Fit & Features

    • Woven straw material
    • Structured top
    • Wide brim, curved sides
    • Shell-beaded accent trim and neck strap
    • Interior elastic band

    Style Number/Barcode: 07302-1612

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Icon Flat Jelly Slide Sandals

    Playful jelly slides that elevate the iconic style you know and love for spring to summer! These fashion sandals feature a sleek square toe, a woven single band, and a comfortable flat sole on jelly material. Complete the look with a statement tote bag for a beach day or outdoor dinner party! 

    Fit & Features

    • Square toe
    • Woven single band
    • Flat sole
    • Slide on-and-off styling
    • Jelly material
    • Runs true to size

    Style Number/Barcode: 07404-1196

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Way With Lace V-Neck Mini Dress

    Let this lace mini dress speak your favorite language, romance! The short dress features a sleeveless V-neckline, spaghetti straps, a bodycon silhouette, and a sheer lace overlay with a sewn-knit lining. Complete the look in rhinestone mules for a wedding shower or birthday brunch!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Sheer lace overlay, sewn-in knit lining
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5088

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winged Goddess Butterfly Rhinestone Mules

    Give your feet goddess vibes in these faux leather mules perfect for glam brides or cocktail soirees! They feature a square toe, a strappy design with butterflies and rhinestone embellishments, and a low-block heel. Complete the look with a sparkly clutch purse.

    Fit & Features

    • Square toe
    • Strappy design
    • Butterflies with rhinestone embellishments
    • Low block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4204

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Admiring Style Strapless Ruffle High Low Denim Dress

    Prepare for plenty of admiring stares when you're in this stylish denim strapless dress! This cute and casual dress features a sweetheart neckline and form-hugging fit, accentuating your curves in all the right places. The patchwork seam detailing adds a touch of unique style, while the high-low ruffled hem adds a playful and flirty element. Complete the look in platform shoes and sunnies!

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffle high low hem
    • Runs true to size

    Style Number/Barcode: 05102-5574

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Fave Espadrille Platform Wedges

    These adorable espadrille platform wedges will be a new fave for sunny weekend plans! With the trendy square toe and thin strappy design, you'll love styling them with your brunch dresses.

    Fit & Features

    • 4" Espadrille wedge heel
    • Open square toe
    • Asymmetric strappy design
    • Adjustable ankle strap with buckle detail
    • Platform design
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07406-0363

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dial B For Basics Square Neck Mini Dress

    Dial B for this basic mini dress that'll inspire all your fashion-forward looks! It features a sleeveless square neckline, sleek bungee spaghetti straps, a form-hugging silhouette, and a mini-length hem. The double-line buttery knit fabric offers a seamless design and plenty of stretch. Style with a minimalistic necklace and earrings to inspire your day or night outfit! 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Form-hugging silhouette
    • Mini-length hem
    • Double-lined buttery knit fabric, moderate stretch
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 05102-5134

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Style Crochet Hanky Hem Halter Top

    Channel that trendy boho-chic style with this crochet knit halter top! The high halter neckline leads to a bold open-back design with cross-back tie straps offering an adjustable fit. The cropped asymmetric hanky hem will create a snatched look on the form-hugging silhouette. Pair with high-rise jeans and strappy sandals for a casual summer vibe.

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Halter neckline
    • Open back with cross-back tie straps
    • Asymmetric hanky hem
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06005-1958

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Cute Eyelet Lace Mini Dress

    Achieve an effortless pretty and cute style in this eyelet lace mini dress for your casual dates or strolling downtown with the girls! The dress features adorable puff short sleeves, a ruffle trim sweetheart neckline with a front bust tie, a bodycon fit, and side ruching with an adjustable tie. Complete the look in trendy flat sandals.

    Fit & Features

    • Puff short sleeves
    • Ruffle trim sweetheart neckline
    • Front bust tie
    • Bodycon silhouette
    • Side ruching with adjustable tie
    • Mini-length hem
    • Eyelet lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4912

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed And Cute Polka Dot Chiffon Skater Dress

    Envoke a charmed and cute style in this polka dot skater dress perfect for showers or graduates! Show off your curves with the sweetheart neckline and skater silhouette, while adding a touch of cuteness with the short puff sleeves. The tie-back adds a flirty detail and the short-length hem is perfect styling with trendy sneakers for a casual vibe.

    Fit & Features

    • Polka dot, chiffon fabric, woven lining, no stretch
    • Sweetheart neckline
    • Padded bra cups
    • Back zipper hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3289

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Queen Tropical Floral Mesh Maxi Skirt

    Slay your next vacay in this gorg tropical floral mesh maxi skirt with a mini-length lining and a high-cut side slit. Style with the matching crop top for a sultry vibe!

    Shop Matching Top: Vacay Queen Tropical Floral Mesh Tie-Front Top

    Fit & Features

    • Sheer mesh fabric with mini-length knit lining, high stretch
    • Large tropical floral print
    • Mid-rise waist
    • Hip-hugging fit
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000030

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Cozy Feels Faux Fur Knit Beanie

    Keep your winter 'fit cozy with this adorable knit beanie! It features a ribbed fold-over hem, a cable knit design, an ultra-plush faux fur lining to keep you warm, and a top fuzzy faux fur pom detail. Style this cute beanie with your favorite sweater.

    Fit & Features

    • Ribbed fold-over hem
    • Cable knit design
    • Soft faux fur lining
    • Faux fur pom

    Style Number/Barcode: 07302-0988

    Category Name: Vacation Looks

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Era Woven A-Line Midi Dress

    Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.

    Fit & Features

    • Poplin smooth cotton woven fabric with full-length woven lining
    • Sleeveless square neckline, adjustable spaghetti straps
    • Stretchy smocked bodice
    • V-shaped waist
    • Pleating, hidden side pockets
    • Midi-length flowy A-line silhouette, high side slit
    • Runs true to size

    Style Number/Barcode: 05102-000001

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Classic Fold-Over Ribbed Knit Beanie

    This cute classic ribbed knit beanie is a winter must-have! It features a thick ribbed knit material with a fold-over design and offers moderate stretch. Style this adorable beanie with a fuzzy faux sherpa jacket.

    Fit & Features

    • Thick ribbed knit material
    • Fold-over design
    • Moderate stretch

    Style Number/Barcode: 07302-1514

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Babe Button Up Linen Vest

    A sleek fit with tailored details, this sleeveless linen vest is essential for spring-to-summer wear! The vest is designed with a flattering V-neckline, button-up front closures, and a curved cropped hem to flaunt your figure. Complete the look with the matching pants.

    Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants

    Fit & Features

    • Lined linen fabric
    • Button up front closures
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1737

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Perfection Bodycon Striped Mini Dress

    With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!

    Fit & Features

    • Striped pattern, texture knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline with twist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5675

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Babe Tie-Back Crochet Mini Dress

    Channel a beachy babe vibe in this trendy crochet mini dress! Designed with a sheer crochet fabric with a boho-inspired woven design, the short dress includes a stretchy knit lining for coverage. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, an adorable tie-back design, a flirty lower back cutout that peaks out on both sides, and a form-hugging fit to flaunt your figure. Style with espadrille sandals.

    Fit & Features

    • Crochet fabric with woven design, stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Tie back straps, back cutout
    • Hidden side zipper with hook and eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5780

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Vibes Floral Halter Crop Top

    Your plus-one to every fun night out. This floral halter crop top drapes effortlessly with a flirty cowl neckline and beaded accents that bring the perfect chic touch.

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, high stretch
    • Floral print
    • Sleeveless cowl neckline
    • Halter tie-back spaghetti straps, beaded accents
    • Open back, lower tie-back spaghetti straps, beaded accents
    • Cropped hanky hem
    • Runs true to size

    Style Number/Barcode: 06001-000262

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Bri High-Rise Flare Jeans by Windsor Denim

    Keep your casual everyday 'fits trendy with the Bri high-rise flare jeans. This pair by Windsor Denim features a fitted high-rise waist, destructed detailing at the knees, and a fab flare hem. The denim fabric offers a moderate stretch for comfortable wear. Style with a bodysuit and mules.

    Fit & Features

    • High-rise waist
    • Destructed detailing at the knees
    • Fitted silhouette, flare hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0354

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Instant Fave Disty Floral Short Sleeve Midi Dress

    This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Crew neckline, short sleeves
    • Small back keyhole cutout, button closure
    • Larger lower back cutout, high waist seam
    • Midi-length hem, front slit, form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5184

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale