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.

  • Romantic Vibes Floral Mesh Midi Dress

    Hey babe, bring the romantic vibes to your next dinner date in this floral mesh midi dress! It features a sleeveless cowl neckline, bungee spaghetti straps, and a mid-length, curve-hugging silhouette. The sheer mesh fabric has a pretty all-over floral print with a full knit lining. Complete the look with strappy heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Bungee spaghetti straps
    • Mid-length, form-hugging fit
    • Sheer mesh fabric, knit lining, floral print
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1094

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daring Diva Open Back Midi Dress

    Dare to go bold with a midi dress that wows! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a midi-length silhouette. Complete look with stilettos and door knocker earrings

    Fit & Features

    • Sleeveless scoop neckline 
    • Adjustable spaghetti straps, cross at back
    • Open back 
    • Midi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1210

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Adventure Awaits Panama Hat

    Look oh-so-chic as you set out on your next adventure in this trendy Panama hat. It features a wide flat brim and a thin band with a tie accent. Style this hat with a cute crossbody purse.

    Fit & Features

    • Wide flat brim
    • Thin band, tie accent
    • Faux wool material

    Style Number/Barcode: 07302-0385

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out And About Panama Hat

    Get ready to look stylish and chic as you are out and about with this on-trend Panama hat! It features a wide flat brim and a basic ribbon band. Pair this hat with sleek hoop earrings.

    Fit & Features

    • Wide flat brim
    • Basic ribbon band
    • Faux wool material

    Style Number/Barcode: 07302-0384

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Crew Ribbed Knit Mini Dress

    Show em' all that you roll with the chic crew in this fab mini dress! The dress features a crew neckline with a racer bust, a ruched body, and a mini side slit. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Ruching
    • Mini side slit
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-4240

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Sleek Panama Hat

    Top off your look with this stylish Panama hat for an effortless trendy vibe! It features a wide flat brim and a thin adjustable ribbon band with a sleek triangle-shaped buckle. Complete the outfit with cute ankle booties.

    Fit & Features

    • Wide flat brim
    • Thin adjustable ribbon band
    • Triangle-shaped buckle
    • Faux wool material

    Style Number/Barcode: 07302-0386

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Sparkle Rhinestone Slides

    Bring a sparkly style to your everyday look with these fab embellished slides. They feature an open square toe, a wide toe strap with all-over rhinestone embellishment, and a glam chrome sole. Pair these slides with a trendy ring pack.

    Fit & Features

    • Open square toe
    • Wide toe strap, rhinestone embellishment
    • Chrome sole
    • Runs true to size

    Style Number/Barcode: 07404-0927

    Category Name: Vacation Looks

    Price: $10.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek And Strappy Studded Jelly Sandals

    Keep it sleek and stylish with sandals that slay your look! The sandals feature an adjustable ankle strap, multiple straps, pyramid-shaped studs, and an open almond toe. Complete look with a denim mini dress and hoops. 

    Fit & Features

    • Adjustable ankle strap
    • Multiple strap design 
    • Pyramid-shaped studs
    • Open almond toe
    • Jelly material 
    • Runs true to size

    Style Number/Barcode: 07404-0832

    Category Name: Vacation Looks

    Price: $7.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Stunner Cutout Midi Dress

    Stand out like the major stunner you are with a midi dress that brings the style! The dress features a plunging halter neck with a V-neck bust, a cutout at the midriff with sleek straps, and a midi-length silhouette with a high side slit. The dress is composed of a lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Halter neck, V-neck bust
    • Cutout at the midriff with straps
    • Midi length silhouette
    • High side slit
    • Lurex knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4157

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Reign In Glam Rhinestone Sandals

    Reign in luxe with sandals that show how extra you are! The sandals feature a slip-on design, rhinestone embellished straps, an asymmetrical strap, and an open almond toe. Complete look with a ruched mini dress and hoops. 

    Fit & Features

    • Slip-on design 
    • Rhinestone embellished straps
    • Asymmetrical strap
    • Open almond toe
    • Faux leather material 
    • Runs true to size

    Style Number/Barcode: 07404-0930

    Category Name: Vacation Looks

    Price: $7.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Banded Panama Hat

    Bring your look together with this trendy panama hat! The hat features a panama design and a banded hem around the brim. Complete the look with a romper and sandals.

    Fit & Features

    • Panama design
    • Wide brim
    • Banded hem

    Style Number/Barcode: 07302-0381

    Category Name: Vacation Looks

    Price: $8.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhinestone Hoops And Studs Six Earring Pack

    Add a hint of sparkle to your look with a dazzling pair of earrings! The variety pack includes six pairs of earrings. The earrings feature rhinestone embellished hoops that come in varying sizes, rhinestone studs, butterfly studs, and cross charm studs. Complete look with a white dress and wedges. 

    Fit & Features

    • Pack includes six pairs of earrings
    • Hoops in varying sizes
    • Rhinestones
    • Butterfly studs
    • Cross charm studs

     

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

    Style Number/Barcode: 07001-0842

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful Cutie Halter Cutout Skater Dress

    Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Halter neckline with spaghetti strap ties
    • Stretchy smocked bust
    • Cutout bodice
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6016

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: S, L

    Product Badge:
    • Sale
  • Dainty Details Cubic Zirconia Teardrop Necklace

    Showcase dainty details with a layered necklace that brings the glam to your outfit! The necklace features a two-row layered design, a round-shaped cubic zirconia stone, a teardrop-shaped cubic zirconia stone, and a lobster clasp closure. Complete look with matching coordinates and heels.

    Fit & Features

    • Dainty chain link
    • Two-row design
    • Round-shaped zirconia stone
    • Teardrop-shaped zirconia stone
    • Lobster clasp closure

    Style Number/Barcode: 07002-0845

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Chain Coin Charm And Cross Necklace Set

    Layer on the style with a trendy necklace that brings the glam to your look! The pack includes four necklaces that create a layered five-row design, two coin charms, and a rhinestone embellished cross charm. Complete look with a bustier and high waist jeans. 

    Fit & Features

    • Pack includes four necklaces
    • Dainty chain link, snake chain
    • Two coin charms
    • Cross charm
    • Rhinestones 
    • Lobster clasp closure 

    Style Number/Barcode: 07002-0849

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Queen Espadrille Platform Sandals

    Yes babe, you'll be a total vacay queen on your next getaway in these trendy platform sandals! They feature an open round toe, faux leather straps with an adjustable ankle strap, and an espadrille platform with a flat sole. Style these sandals with a floral dress and cute sunnies.

    Fit & Features

    • Open round toe
    • Faux leather straps
    • Adjustable ankle strap, buckle detail
    • Espadrille platform, flat sole
    • Runs true to size

    Style Number/Barcode: 07404-0920

    Category Name: Vacation Looks

    Price: $13.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Ditsy Floral Cutout Mini Dress

    Let your beauty bloom with a gorge mini dress that reveals your sweet side! The dress features a ditsy floral print, a sleeveless V-neckline, a ruched drawstring at the center, spaghetti straps, a cutout at the midriff, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket

    Fit & Features

    • Ditsy floral print
    • Sleeveless V-neckline
    • Ruched drawstring at the bodice
    • Spaghetti straps
    • Cutout at midriff
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4126

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Flowy A-Line Mini Dress

    Get an effortless look in this flowy boho-chic mini dress. It features a sleeveless subtle square neckline, adjustable spaghetti straps that lead to a cross-back design, a short A-line silhouette, and a drop hem with a cute ruffle detail. Style this dress with your fave pair of wedges.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Cross-back design
    • Mini-length, A-line silhouette
    • Drop hem, ruffle detail
    • Double-lined gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-3099

    Category Name: Vacation Looks

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living Large Floppy Straw Hat

    Live it up with a straw hat that is perf for your next vacay! The hat features an over straw material, a wide brim, and a cute ribbon-like accent on the brim. Complete look with a white dress and sandals. 

    Fit & Features

    • All over straw material 
    • Wide brim 
    • Ribbon-like accent around brim

    Style Number/Barcode: 07302-0348

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Dreams Lace-Up Mini Dress

    Keep it dreamy with a denim mini dress that elevates your look! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a lace-up back, vertical seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Lace-up back, lower back zipper and hook and eye closure
    • Vertical seams
    • Mini-length silhouette
    • Denim fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4089

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Life Top Handle Bag

    Hey babe, live that luxe life with this chic top handle bag! It features a round design with a wide top handle, a zipper closure, a circular buckle detail, and a detachable shoulder strap to change the bag to a crossbody. The faux leather material has a fab croc-embossed print for a trendy vibe. Style this bag with a pair of oversized sunglasses.

    Fit & Features

    • Round design
    • Wide top handle
    • Zipper closure
    • Circular buckle detail
    • Detachable shoulder strap
    • Faux leather material, croc-embossed print

    Style Number/Barcode: 07203-0770

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Dreams High-Slit Maxi Dress

    This dress is what floral dreams are made of! The dress features a ditsy floral print, a sleeveless sweetheart neckline, a mini tie-front, adjustable spaghetti straps, and a maxi-length silhouette with a high side slit. The dress is composed of a chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Mini tie-front, adjustable spaghetti straps
    • Back zipper and hook and eye closure
    • Ditsy floral print
    • Maxi-length silhouette, high side slit 
    • Chiffon fabric, knit lining, relaxed fit, minimal stretch 
    • Runs true to size 

    Style Number/Barcode: 05101-1074

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ravishing Florals Ruched Mini Dress

    Stun with ravishing florals in a pretty mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, dual ruching that runs from the bodice to hem, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Dual ruching
    • Ditsy floral print
    • Mini length silhouette
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4151

    Category Name: Vacation Looks

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sweet Ruffled Cutout Skater Dress

    Keep it so sweet with a charming ruffled skater dress! The dress features an off-the-shoulder neckline, a smocked bodice with a ruched drawstring, long sleeves, a sexy cutout at the midriff, and a tiered ruffled skater silhouette. The dress is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with sandals

    Fit & Features

    • Off-the-shoulder neckline 
    • Smocked bodice with a ruched drawstring
    • Long sleeves, elastic cinched hems
    • Cutout at the midriff 
    • Tiered ruffle skater skirt
    • Gauze knit fabric, relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2486

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale