Vacation Looks

HomeVacation Looks
Loading...

Now Trending

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.

  • Make Your Debut Strapless Abstract Mesh Maxi Dress

    Make your effortless debut in this abstract mesh maxi dress that hugs your curves in a flattering bodycon silhouette with a long-length hem. Pair with stiletto mules.

    Fit & Features

    • Abstract print, mesh fabric, soft and stretchy knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Long-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4148

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Impressive Blossom Strapless Floral Maxi Dress

    Impress in this floral maxi dress showcasing a sleek strapless neckline and a column silhouette that flatters your figure. Style the dress with a choker.

    Fit & Features

    • Statement floral print
    • Mesh fabric lined with soft, stretch knit
    • Column silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5953

    Category Name: Vacation Looks

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Frame Cat Eye Sunglasses

    Show off these sweet cat eye sunglasses with your stylish looks! 

    Fit & Features

    • Cat eye frame design
    • Tinted lenses

    Style Number/Barcode: 07008-1119

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Is In The Details Lace Lace-Up Skater Dress

    Fall in love with the pretty details on this lace skater dress from the ruffled shoulder straps to the lace-up back design - this dress is a beauty!

    Fit & Features

    • Lace lined fabric
    • Ruffled shoulder straps
    • Sweetheart neckline
    • Lace-up back
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4010

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Date Tie Waist Floral Ruffle Skort

    For your perfect date! Unveil this floral ruffle skort with a high-rise waist and an adorable side tie that cinches your waist. 

    Fit & Features

    • Floral print, woven fabric
    • High-rise waist, side tie
    • Ruffled trim
    • Shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06403-1096

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Look Of Love Floral Lace Ruffled Mini Dress

    You'll fall head over heels for this adorable floral lace mini dress. The strapless corset-inspired bodice pairs perfectly with the ruffled A-line silhouette.

    Fit & Features

    • Sheer floral lace fabric with knit lining, glitter thread accents
    • Moderate stretch
    • Strapless sweetheart neckline with ruffled trim, padded bust, no-slip strip
    • Back zipper with hook-eye closure
    • Corset-inspired bodice, contrast piping, drop waist
    • Tiered ruffled A-line silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3958

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Day To Night Strapless Abstract Slit Maxi Dress

    From day to night, this strapless abstract print maxi dress is an effortless style for any plans!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Strapless neckline
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5905

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cherry Picking Three-Pack Bracelet Set

    This three-pack bracelet set will always be picked first when accessorizing! The set includes one faux pearl and cherry charm bracelet, one chain link bracelet, and one dainty twist chain link bracelet. Pair with earrings.

    Fit & Features

    • Three-pack bracelet set
    • One faux pearl and cherry charm bracelet
    • One chain link bracelet
    • One dainty twist chain link bracelet
    • Each has lobster clasp closures

    Style Number/Barcode: 07003-0672

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Season Strawberry Earrings And Necklace Set

    Celebrate the spring season with this rhinestone strawberry earrings and necklace set perfect for giving your look a sweet touch! Style the jewelry set with a skater dress.

    Fit & Features

    • Matching necklace and earrings set
    • Colored mini rhinestones
    • Strawberry stud earrings, post-back closure
    • Strawberry charm necklace, lobster clasp closure

     

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

    Style Number/Barcode: 07002-2113

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Escape Halter Bodycon Crochet Midi Dress

    Escape on vacay in this must-have halter crochet midi dress perfect for enjoying a sunset dinner and drinks!

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Halter neckline, tie-back
    • Front bust tie with keyhole accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6060

    Category Name: Vacation Looks

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Fling Ditsy Floral Bodycon Mini Dress

    Show off sweet flirty vibes in this adorable ditsy floral mini dress detailed with a ribbon trim and bow detail at the bust. The short bodycon silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Textured knit fabric, high stretch
    • Ditsy floral print
    • Sleeveless sweetheart neckline
    • Ribbon trim with bow detail at the bust
    • Adjustable spaghetti straps
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5763

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Slide Into Spring Platform Straw Sandals

    Slide into these trending platform straw sandals for an effortless spring look! With a wide chain accent band and a comfortable footbed, these shoes are perfect for everyday styling.

    Fit & Features

    • Round toe
    • Wide chain accent band
    • Platform sole
    • Comfortable footbed
    • Traction bottom
    • Runs true to size

    Style Number/Barcode: 07404-1285

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Bound Tropical Floral Ruched Knit Maxi Dress

    Make sure to pack this tropical floral knit maxi dress for your next sunny vacay! The ruched bodycon silhouette will flaunt your stunning curves as you pose for those getaway pics.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Tropical floral print
    • Sleeveless cowl neckline
    • Spaghetti straps
    • Ruching
    • Maxi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6054

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Stunner Floral Mesh Strapless Maxi Dress

    Turn heads your next vacay in this bold floral mesh maxi dress made to impress. The long bodycon silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sheer mesh fabric with full-length brushed knit lining, high stretch
    • Large floral print
    • Strapless straight neckline
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4149

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alluring Vibe Floral Mesh Bodycon Maxi Dress

    Arrive at sunset happy hour in this bold floral mesh maxi dress, an alluring vibe for your next vacay. Turn heads with the halter cowl neckline, backless design, and curve-hugging silhouette.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • Sleeveless cowl neckline, tie-back halter straps
    • Open back
    • Ruching
    • Maxi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000002

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ever So Chic Rhinestone Pearl Sandals

    Step out in these chic flat sandals with a rhinestone and faux pearl embellished strap that elevates every look!

    Fit & Features

    • Square toe
    • Wide band, rhinestone and faux pearl embellished
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1279

    Category Name: Vacation Looks

    Price: $18.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Look Floral Mesh Maxi Dress

    Showcase a gorgeous look perf for dressy birthday parties in this floral mesh maxi dress. The long mermaid silhouette will flaunt your stunning curves as you pose for pics.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • Sleeveless sweetheart neckline, padded bust
    • Adjustable spaghetti straps
    • Partially open back
    • Maxi-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4106

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heartbreaker Status Rhinestone Sunglasses

    Big flirt energy! These rhinestone-trimmed heart frames are here to romanticize your hot girl errands, soft launch your situationship, or just block out bad vibes in style.

    Fit & Features

    • Metal heart-shaped frame
    • Glam rhinestone trim
    • Gradient lenses
    • Nose-pads

    Style Number/Barcode: 07008-000050

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Flirt Lace-Up Ruffle Skater Dress

    Turn heads in a lace-up skater dress with a playful ruffled skirt and hidden side pockets perfect for keeping your hands warm!

    Fit & Features

    • Eyelet lace fabric, woven lining with lace trim
    • Sweetheart neckline, bust tie
    • Adjustable shoulder straps
    • Lace-up back
    • Hidden side pockets
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000037

    Category Name: Vacation Looks

    Price: $31.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Chic Cutout Strap Flat Sandals

    Step into these simply chic flat sandals with a trendy cutout strap that elevates all of your favorite looks!

    Fit & Features

    • Square toe
    • Cutout strap
    • Metallic trim
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1274

    Category Name: Vacation Looks

    Price: $18.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmingly Pretty Beaded Rhinestone Layered Necklace

    Elegance comes naturally when you accessorize with this layered necklace featuring pretty beading and a glam rhinestone accent. Pair with a low-cut blouse or dress.

    Fit & Features

    • Layered necklace
    • Beading and rhinestone accent
    • Lobster clasp closure

    Style Number/Barcode: 07002-2119

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Move Five-Pack Bracelet Set

    Whether you style this five-pack bracelet set together or one by one, it'll always elevate your outfit. The set features four beaded stretch bracelets and one statement stretch bracelet. Pair with a purse.

    Fit & Features

    • Five-pack bracelet set
    • Four beaded stretch bracelets
    • One statement stretch bracelet

    Style Number/Barcode: 07003-0673

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Three's A Crowd Bangle Bracelet Set

    A three-pack bangle bracelet set to complete your looks!

    Fit & Features

    • Three-pack bangle bracelet set

    Style Number/Barcode: 07003-0674

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Chic Sleeveless Ruffled Maxi Dress

    A casually chic sleeveless maxi dress with dreamy warm weather vibes, a flirty bust tie, and a flowy, ruffled silhouette!

    Fit & Features

    • Woven fabric
    • Square neck with bust tie
    • Adjustable spaghetti straps
    • Flowy ruffled silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3465

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free