Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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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.

  • Turn Up The Heat One-Shoulder Cutout Midi Dress

    Turn up the heat in this sultry knit midi dress designed with a one-shoulder neckline, front cutouts, sleek O-ring accents, and a high-cut side slit. The bodycon fit will highlight your gorgeous curves.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Sleeveless asymmetric one-shoulder neckline, gold metal O-ring accent, tank strap
    • Dual front cutouts under the bust and above the waist, gold metal O-ring accent
    • Ruching
    • Midi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000117

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Sweetheart Corset Lace-Up A-Line Short Dress

    Capture sweet vibes in this flirty corset short dress designed with a striking lace-up back design, a corset-style bodice that snatches your waist, and a flattering A-line silhouette. Pair with bow earrings.

    Fit & Features

    • Poplin woven fabric, woven lining
    • Sweetheart neckline with adjustable drawstring tie
    • Adjustable spaghetti straps, lace-up back design
    • Underwire bust, corset-bodice, flexible boning
    • Side zipper and hook-eye closure
    • A-line short silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3780

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Fun Vibes Floral Straw Flat Sandals

    The fun and cute vibes of these sandals will have you living in them all season! They feature a sleek square toe with a floral patterned straw band for a trendy touch and a comfortable flat sole. Complete the look with a cute mini handbag.

    Fit & Features

    • Square toe
    • Floral patterned straw band
    • Flat sole
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1159

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Jetset Babe Tropical Print Belted Maxi Dress

    Jetset to somewhere fabulous in this tropical print maxi dress! The flattering belted waist cinches your silhouette while hidden side pockets add convenience. A sultry side slit creates movement for a trendy look.

    Fit & Features

    • Tropical multi-print, woven fabric
    • Strapless neckline
    • Belted waist
    • Hidden side pockets
    • Flowy maxi silhouette, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000112

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Match My Energy Eyelet Skater Dress

    This adorable dress will have you feeling cute and carefree for any fun plans! The strapless neckline, ruffled skater silhouette, and eyelet print add a touch of playfulness to your everyday look.

    Fit & Features

    • Eyelet fabric, sewn-in knit lining
    • Strapless neckline
    • Strappy back
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000108

    Category Name: Vacation Looks

    Price: $9.97 $65.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Speechless Strapless Floral Ruffle Mini Dress

    Leave everyone speechless when you stroll in wearing this floral mini dress at parties or brunch! The strapless neckline and stretchy smocked bodice provide a comfortable and flattering fit, while the dainty floral print and embroidery add a touch of whimsy. Complete the look with sunnies.

    Fit & Features

    • Dainty floral print and embroidery
    • Woven fabric, some stretch
    • Fitted silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4007

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: L

    Product Badge:
    • Sale
  • Texas Sun Frayed Straw Panama Hat

    Designed to keep you cool and stylish under the sun, this panama hat features a frayed straw design with a wide brim and inner adjustable strings for a snug fit. Complete the look in cute cowboy boots for your next trip.

    Fit & Features

    • Frayed straw design
    • Wide brim
    • Inner adjustable strings

    Style Number/Barcode: 07302-1631

    Category Name: Vacation Looks

    Price: $4.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling For You Tropical Floral Slit Maxi Dress

    Get the golden hour glow in this tropical floral maxi dress while on vacation! Featuring a chic square halter neckline and a form-hugging fit with a high side slit, this dress beautifully accentuates your silhouette.

    Fit & Features

    • Tropical floral print, mesh-lined fabric
    • Square halter neckline, adjustable spaghetti straps
    • Criss cross back
    • Form-hugging silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6113

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Alignment Celestial Layered Necklace

    All the stars and planets aligned to inspire this celestial layered necklace! It features dual dainty chain links with a rhinestone moon and star charm. Complete the look in a bustier and jeans for going out!

    Fit & Features

    • Dual dainty chain links
    • Rhinestone moon and star charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-1830

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Sweet Floral And Plaid Patchwork Mini Dress

    Create the perfect weekend look in this oh-so-sweet mini dress designed with a floral and plaid patchwork pattern. The crochet bust trim and tie-front detail are dainty details you'll adore.

    Fit & Features

    • Woven fabric, no stretch
    • Ditsy floral and plaid patchwork pattern
    • Sleeveless sweetheart neckline, crochet trim and tie-front detail, ruched bust
    • Adjustable spaghetti straps
    • Hidden back zipper, hook-eye closure
    • Mini-length hem, fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000178

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: M

    Product Badge:
    • Sale
  • Covetable Layered Rhinestone Charm Necklace Set

    Elevate your looks by pairing them with this layered rhinestone charm necklace set! It features a snake chain choker, a dainty chain with a sparkly rhinestone charm to add a glam effect, and a flat dainty chain for a trendy vibe. Complete the look in a strapless dress for dinner and drinks!

    Fit & Features

    • Layered necklace set
    • Snake chain choker
    • Dainty chain with rhinestone charm
    • Flat dainty chain
    • Back adjustable chains with lobster clasp closures

    Style Number/Barcode: 07002-1839

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Unforgettably Sweet Floral Bodycon Ruffle Mini Dress

    Create an alluring look in this floral mini dress in a bodycon fit with a flirty ruffled hem. Perfect for shower celebrations and graduations!

    Fit & Features

    • Floral print, lace-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5985

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Darling Ditsy Floral V-Neck Mini Dress

    This ditsy floral mini dress will have you dreaming of sunshine days! Flaunt your figure with the bodycon fit of this dress showcasing a flattering V-neckline, dainty spaghetti straps, a tie-front bust for added detail, and a mini-length hem on ditsy floral print mesh fabric. Complete the look in sandals and a mini tote bag.

    Fit & Features

    • Ditsy floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Slit accent
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5571

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Day Scoop Neck Ruffle Eyelet Skater Dress

    The sweetest days are spent in this eyelet skater dress soaking up the sun with pretty details like sheer trim designs and a ruffled mini-length hem.

    Fit & Features

    • Eyelet lace fabric, stretchy knit lining
    • Scoop neckline, ruffle trim
    • Adjustable spaghetti straps
    • Sheer trim designs on the bodice
    • Ruffled tier mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3936

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Falling For Charm Strappy Open Back Floral Mini Dress

    Fall for the charm of this flirty floral mini dress with a head-turning strappy open back and A-line fit perfect for showing off at brunch or a spring date!

    Fit & Features

    • Floral print, stretchy knit fabric
    • Halter V-neckline, spaghetti strap tie
    • Open back, strappy spaghetti strap ties
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6042

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sitting In The Sun Floral Babydoll Mini Dress

    So charming for sunny days, this floral babydoll mini dress is fit for frolicking downtown to brunch or attending a shower!

    Fit & Features

    • Floral print, eyelet woven fabric, chiffon lining
    • Square neckline
    • Wide adjustable shoulder straps
    • Stretchy smocked bust
    • Flowy ruffled babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4002

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Head-Turning Flirt Bodycon Mini Dress

    A bodycon mini dress that makes the perfect foundation to create flirty looks!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000086

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Touch Pearl Flower Strap Cork Wedges

    Hello 2024 brides! Add a whimsical touch to your bridal looks with these pearl flower strap cork wedges perfect for engagement parties, bachelorettes, or rehearsal dinners! Made with smooth faux leather, they feature an open almond-shaped toe, a toe strap accented with chic chiffon flowers with center faux pearl detailing, thin adjustable ankle and heel straps, and a tall cork wedge heel for added lift and support. Style with elegant jewelry.

    Fit & Features

    • 4" Cork wedge heel
    • Faux leather upper
    • Open almond toe
    • Toe strap with chiffon flowers with faux pearl details
    • Adjustable ankle and heel straps, buckle closure
    • Padded insole
    • Runs true to size

    Style Number/Barcode: 07406-0340

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Dreamer Strapless Bodycon Lace Mini Dress

    You'll be graced by lace in this bodycon mini dress as the lovely bride-to-be, birthday cutie, or graduate girlie!

    Fit & Features

    • Laced lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3824

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: M

    Product Badge:
    • Sale
  • Sunny Days Square Neck Tie-Back Skater Short Dress

    Sunny days pair perfectly with this skater short dress for casual occasions or day dates! Made from lightweight cotton, this dress boasts a square neckline and elasticized cap sleeves for a perfectly feminine touch. The smocked bodice and tie-back waist ensure a flattering fit, while the tiered skater silhouette adds a playful flair. Complete the look with sandals, sunglasses, and a purse for a cute style!

    Fit & Features

    • Lightweight cotton fabric with woven lining
    • Stretchy smocked bodice
    • Tie-back waist
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5417

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Charmer Ditsy Floral Strapless Mini Dress

    Charm them with your adorable style in this lined eyelet knit mini dress with the cutest ditsy floral print. The form-hugging fit will highlight your curves.

    Fit & Features

    • Sheer eyelet knit fabric with knit lining, high stretch
    • Ditsy floral print
    • Strapless straight neckline
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6046

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Majorly Tropical Plunge Halter Wide-Leg Jumpsuit

    Grab some shades and throw on this tropical plunge halter wide-leg jumpsuit for majorly vacay vibes on your getaway or weekend escape! Featuring a sultry plunge halter neckline with button closures and an open tie-back design, this jumpsuit effortlessly is a sexy style. The wide-leg silhouette and tropical palm print on knit fabric add a touch of tropical flair to any look. Complete the look with sunglasses and a floppy hat!

    Fit & Features

    • Tropical palm print, knit fabric, bust lining, stretchy
    • Plunge neckline with button closures
    • Open tie back design
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2455

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Romance Corset Lace-Up Floral A-Line Mini Dress

    The flirty romantic allure of this floral mini dress will take you from brunch and garden party soirees! This mini dress boasts a cinched waist with a corset bodice and head-turning lace-up back design while the a-line silhouette flatters your figure. Pair with ballet flats.

    Fit & Features

    • Dainty floral print, poplin woven fabrication
    • Sweetheart neckline with bust tie, underwire bust
    • Adjustable spaghetti straps
    • Corset bodice, lace-up back, flexible boning
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3768

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Wild Thing Zebra Print Statement Earrings

    Hey there wild thing! You'll be looking fierce in these zebra statement earrings featuring a textured post and a zebra-printed shell with glitter accents. Includes a post-back closure. Complete the look in a trendy denim jumpsuit for any occasion!

    Fit & Features

    • Textured post
    • Zebra print shell with glitter accents
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2035

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free