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.

  • Summer Dreams Halter V-Neck Boho Chiffon Maxi Dress

    Summer dreams are made of this boho chiffon maxi dress perfect for your vacation or weekend getaway! The halter V-neckline and spaghetti strap tassel ties provide an effortlessly chic touch, while the stretchy smocked bodice and hidden side pockets offer convenience. The flowy ruffled silhouette adds a touch of romance! Complete the look in sandals and a bracelet.

    Fit & Features

    • Bohemian print, chiffon fabric with woven lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Hidden side pockets
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5777

    Category Name: Vacation Looks

    Price: $6.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Timeless Staple Mid-Rise Button Denim Skort

    All buttoned up, this mid-rise denim skort is a true timeless staple.

    Fit & Features

    • Medium wash denim fabric
    • Mid-rise waist
    • Button-up front closures
    • Form-hugging fit, shorts bottom
    • Mini-length hem
    • Back pockets, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-0486

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: XS, S, M, L

  • Spring Breeze Sweetheart Tie Eyelet Crop Top

    Spring into the new season in this eyelet crop top for vacations or weekend fun! Featuring a playful sweetheart neckline and delicate spaghetti straps, this top will keep you feeling cool and confident. The tie front adds a touch of charm, while the cropped hem and eyelet lace fabric offer a romantic and airy look. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Spring Breeze Ruffled Eyelet Maxi Skirt

    Fit & Features

    • Eyelet lace fabric, slight stretch
    • Spaghetti straps
    • Tie front
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5282

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Trend Layered Bead Necklace

    Achieve an on trend look with this layered necklace featuring colored beads that give your outfit a refreshing update! Complete the look with sandals.

    Fit & Features

    • Layered design
    • Colored beads
    • Lobster clasp closure

    Style Number/Barcode: 07002-1861

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Under The Sun Tropical Tie-Front Crop Top

    Perfect for any vacation or resort escape, this tropical top boasts a sultry tie-front and a cropped silhouette for a breezy allure. Pair with the matching skirt.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Long sleeves
    • V-neckline
    • Tie-front closure
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Skirt: Under The Sun Tropical Slit Maxi Skirt

    Style Number/Barcode: 06202-000014

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Hey Shorty High-Rise Cut Off Denim Shorts

    Hey, shorty looking cute in these high-rise denim shorts! Perfect for any spring or summer plans, these shorts fit just the way you want and flatter from every angle. The high-rise waist and form-hugging fit hug your figure, while the distressed accents and cut-off hem add a touch of edgy style. Complete the look in a flirty crop top.

    Fit & Features

    • Denim fabric with stretch
    • High-rise waist, hidden front button and zipper closure
    • Distressed accents, five-pocket styling
    • Cut off hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0378

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Vacay High Slit Tropical Mesh Midi Dress

    Dare to allure on your next vacay in this sultry high slit tropical midi dress! The airy-lined mesh fabric is detailed with a bold all-over tropical palm leaf print to bring those dreamy destination vibes to your look. The mid-length dress features a sleeveless square neckline with pleating, spaghetti straps that lead to an open cross-back strappy design, a high-cut side slit to show off some leg, and a slim-fit silhouette to flaunt your figure. Style with hoop earrings and sandals for a beachy-chic outfit.

    Fit & Features

    • Tropical print
    • Stretchy mesh fabric with knit lining
    • Square neckline
    • Spaghetti straps, open cross-back strappy design
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5688

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanderlust Mode Wide-Leg Pants

    Crush your style game in these wide-leg pants. With a smooth knit and flared hem, these pants bring effortless chic to your every move. Perfect for your next adventure!

    Shop Matching Top: Wanderlust Mode Cutout Tube Top

    Fit & Features

    • Smooth knit fabrication with stretchy knit lining
    • Mid-rise waist
    • Straight-leg fit
    • Flared wide-leg hem
    • Pants in size small have an 11" front rise with a 28" inseam
    • Runs true to size

    Style Number/Barcode: 06502-2569

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RUST

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Stars Align Filigree Earrings

    The stars have aligned and these earrings belong in your jewelry box. They feature a metal filigree design and a rubber-back stopper for a secure fit. Complete the look in a sleek bodycon dress.

    Fit & Features

    • Metal filigree design
    • Rubber-back stopper

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-1264

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple And Chic Ponte Knit Mini Skort

    Simple and chic, this ponte knit mini skort will elevate your casual looks. It features a mid-rise waist, a mini-length overlay with a double slit design, and hidden shorts for coverage.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Mid-rise waist
    • Mini-length overlay
    • Double slit side design
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000066

    Category Name: Vacation Looks

    Price: $27.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, L

  • Spring Vibes Daisy Studded Jelly Tote Bag

    This adorable jelly tote bag is the perfect accessory for your fab spring festivities! Made with a trendy jelly material, this tote features a small rectangular design with adorable daisy-studded accents. Includes two top handle straps and a removable long chain-link shoulder strap. Style with a flowy skater dress and heels for weekend brunch!

    Fit & Features

    • Jelly material
    • Small rectangular design
    • Small daisy-studded accents
    • Dual top handle straps
    • Foldover with snap-button closure
    • Removable chain-link shoulder strap, lobster clasps

    Style Number/Barcode: 07203-1983

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Glam Rhinestone Pearl Buckle Slide Sandals

    Adorn your feet in these glam rhinestone faux pearl slide sandals with dual buckle straps and a comfortable footbed. Pair with a tote bag for a beach day.

    Fit & Features

    • Round toe
    • Dual buckle straps with rhinestone, faux pearl trim
    • Comfortable footbed
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1284

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 5.5, 7, 7.5, 8, 9

  • Time For Vacay High Rise Tropical Palazzo Pants

    These tropical palazzo pants are ready for your next vacay! Features a high-rise waist and wide-leg silhouette for a flattering fit. The palm print on knit fabric adds a touch of paradise to any outfit. Complete the look with the matching top.

    Shop Matching Top: Time For Vacay Tie Front Tropical Crop Top

    Fit & Features

    • Palm print, stretchy knit fabric
    • High rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2482

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Bound Cutout Tropical Mesh Midi Dress

    You'll be ready for your trip with this tropical mesh midi dress! This dress features a square neckline, spaghetti straps, and a bodycon fit for a flattering silhouette. The side cutout drawstring adds a touch of fun while the side slit and midi-length offer a sultry feel. Complete the look in trendy sandals.

    Fit & Features

    • Tropical palm leaf print
    • Mesh fabric, stretchy knit lining
    • Spaghetti straps
    • Square neckline
    • Side cutout drawstring
    • Bodycon fit, side slit
    • Runs true to size

    Style Number/Barcode: 05102-5710

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Muse Watercolor Tie-Front Crop Top

    Showcase your iconic style like the chic muse you are in this printed tie-front crop top! Crafted from a breezy woven fabric, it is detailed with a gorgeous watercolor print for a mesmerizing look. The top features a sleeveless V-neckline with a tie-front design at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a fitted cropped hem. Style with the matching midi skirt and espadrille wedges for a sunset dinner!

    Shop Matching Bottoms: Chic Muse Watercolor Wrap-Slit Midi Skirt

    Fit & Features

    • Watercolor print
    • Woven fabric
    • V-neckline, tie-front
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2518

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Muse Square Sunglasses

    Serving low-effort luxe from sunrise to happy hour. These square sunglasses give effortless it-girl vibes with a sleek metal frame that pairs with everything from linen sets to poolside 'fits.

    Fit & Features

    • Curved square-shaped design
    • Thin metal frame
    • Thin arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000055

    Category Name: Vacation Looks

    Price: $11.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

  • Flirty Fling Heart-Shaped Sunglasses

    Flirt up a storm in these adorable heart-shaped sunglasses perfect for the summer season! Featuring the cutest heart-shaped design with tinted lenses, these shades have a sleek thin metal frame with thin arms, a thin metal nose bridge, and rubber nose pads for support. Style with hoop earrings for a music festival!

    Fit & Features

    • Heart-shaped design
    • Tinted lenses
    • Thin metal frame and arms
    • Thin metal nose bridge
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1048

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Gaze Chain Trim Cat Eye Sunglasses

    Slip on these cat eye sunglasses knowing you're the cutest babe around! The chain trim arms add a touch of edge while the tinted lenses help protect your eyes from the sun.

    Fit & Features

    • Chain trim arms
    • Cat eye shaped frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1134

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stroll In The Sand Halter Crochet Crop Top

    Make waves by the shore in this crochet top with a flirty halter V-neckline and crop hem that flaunts your figure. Pair with a flowy maxi skirt for any casual plans!

    Fit & Features

    • Crochet knit fabric
    • Halter V-neckline, spaghetti strap tie
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06005-000030

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: CHARTREUSE, WHITE

    Available Size: S, M, L

  • Cool Girl Chic Strapless Abstract Mesh Mini Dress

    Keep your going-out look cool girl chic with this sultry strapless abstract mesh mini dress. The airy sheer mesh fabric showcases a trendy abstract print and includes a full-length soft knit lining for coverage. The strapless straight-across neckline features an elastic band for a stretchy and secure fit, while the bodycon silhouette will flaunt your stunning curves. Style this short dress with a layered necklace and lace-up heels for drinks with the girls!

    Fit & Features

    • Stretchy sheer mesh fabric with soft knit lining
    • Abstract print
    • Strapless straight elasticized neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5558

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Reputation Halter Cutout Ribbed Knit Midi Dress

    It's easy to keep up with your stylish reputation with this ribbed knit midi dress! Perfect for vacation or weekend plans, this midi dress boasts a trendy halter neckline with tie straps, sultry side, and back cutouts that flaunt some skin, and a bodycon silhouette adorned with a front slit. Complete the look with sunglasses and a cute purse!

    Fit & Features

    • Ribbed knit fabric, moderate stretch
    • Halter neckline with tie straps
    • Cutout side and back
    • Front slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2000

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Bloom Floral Mesh Tube Top

    Serve a sultry vibe in this blooming floral printed mesh tube top! Designed with ruched side seams to show off your curves, style with the matching maxi skirt for a gorgeous look.

    Shop Matching Bottoms: Sultry Bloom Floral Mesh Maxi Skirt

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Strapless straight neckline, no-slip strip
    • Ruched side seams
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-5714

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: MAGENTA

    Available Size: M, L, XL

    Product Badge:
    • Part of a Set
  • Shine Shocker Rhinestone Strappy Flat Sandals

    Step into the spotlight in these rhinestone strappy flat sandals at parties or on vacation! These stunning sandals feature a round toe with a metallic strap, along with rhinestone embellished asymmetrical straps for a touch of sparkle. The closed metallic ankle with a zipper closure and adjustable ankle strap with buckle provide the perfect fit for all-day comfort. Complete the look in a cute romper or jumpsuit.

    Fit & Features

    • Flat sole, faux leather material
    • Round toe with metallic strap
    • Rhinestone embellished straps
    • Closed ankle with zipper closure
    • Adjustable ankle strap with buckle
    • Runs true to size

    Style Number/Barcode: 07404-1191

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Oasis Halter Crochet Crop Top

    Keep things trendy on vacation in this crochet crop top and inspire your mermaid core aesthetic!  The halter neckline and spaghetti strap tie provide a flattering fit, while the padded bra cups offer support. Featuring a cropped hem and open back with tie closure, this top is perfect for adding a touch of style. Complete the look in a denim midi skirt and sandals!

    Fit & Features

    • Non-stretch crochet fabric
    • Halter neckline, spaghetti strap ties
    • Padded bra cups
    • Open back with tie closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06005-1973

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale