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.

  • Keep It Chic And Cozy Blanket Scarf

    Keep your look chic and cozy bundled up in this woven scarf! It features a checkered print with neutral tones, fringe detailing at the hems, and an oversized blanket fit. Style this soft scarf with a faux leather jacket and booties.

    Fit & Features

    • Checkered print
    • Neutral tones
    • Fringe detailing
    • Oversized blanket fit
    • Woven fabric, no stretch

    Style Number/Barcode: 07305-0366

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Wild Leopard Knit Vest

    Channel your wild side with a vest that can be layered over your favorite long sleeve tops. The vest features a trendy leopard print, a sleeveless V-neckline, and a ribbed hem. The vest is composed of a soft-to-the-touch knit fabric that offers a relaxed fit with a moderate stretch. Complete look with combat boots.

    Fit & Features

    • Sleeveless V-neckline
    • Leopard print
    • Ribbed hem 
    • Knit fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1110

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fashion Puff Quilted Stiletto Booties

    The perfect puff stiletto bootie every fashionista needs! They feature a pointed toe, quilt pattern, and a cinched ankle with a self-tie. Complete your look with edgy joggers.

    Fit & Features

    • Pointed toe
    • Quilt pattern
    • Stiletto heel
    • Cinched ankle, self-tie
    • Faux leather
    • Runs true to size

    Style Number/Barcode: 07403-1315

    Category Name: Vacation Looks

    Price: $12.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Edge Trendy Lug Sole Bootie

    Take your style to the edge in this lug sole bootie featuring a round toe, block heel, on faux leather material. It features elasticized inserts for easy on/off styling. Complete your look with a trench coat and jeans. 

    Fit & Features

    • Round toe
    • Block heel
    • Elasticized side inserts for easy on/off styling
    • Lug sole 
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1337

    Category Name: Vacation Looks

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Chelsea Lug Sole Booties

    The classic Chelsea bootie in a trendy lug sole! This bootie features a round toe design, block heel, and elasticized inserts for easy on/off styling on a faux suede material. Complete your edgy-chic look with distressed jeans. 

    Fit & Features

    • Round-toe design
    • Block heel
    • Elasticized inserts for easy on/off styling
    • Lug sole
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07403-1338

    Category Name: Vacation Looks

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Vacay V-Neck Floral Maxi Dress

    Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4076

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tough Chic Lug Sole Booties

    Edge up your everyday look in this lug sole bootie! It's designed with an almond toe, block heel, and elasticized inserts for easy on/off styling. The bootie is composed of faux leather material. Complete the look in joggers.

    Fit & Features

    • Almond toe
    • Block heel
    • Elasticized inserts for easy on/off styling
    • Lug sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1327

    Category Name: Vacation Looks

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Glam Chain Detail Panama Hat

    Bring the trendy glam vibes to your everyday look with this faux wool Panama hat. It features a wide flat brim with a center chunky chain-link accent trim. Pair this hat with basic hoop earrings.

    Fit & Features

    • Wide flat brim
    • Chunky chain-link trim
    • Faux wool material

    Style Number/Barcode: 07302-0425

    Category Name: Vacation Looks

    Price: $7.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Swag Rhinestone Layered Necklace

    Showcase your edgy-glam style in this layered necklace! It features two layers including a chain-link and rhinestone drop on a dainty chain. Compliment your look with a chic bodysuit.

    Fit & Features

    • Two layers
    • One chain-link
    • One dainty chain with rhinestone drop
    • Lobster clasp closure

    Style Number/Barcode: 07002-1031

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Moment Faux Wool Panama Hat

    Create a bold moment with a hat that answers the call for adventure, babe! The hat features a traditional Panama design, a trendy ribbon around the brim, and is composed of a faux wool material. Complete look with a babydoll dress and ankle booties for those bohemian vibes. 

    Fit & Features

    • Traditional Panama design 
    • Ribbon trim 
    • Faux wool material 

    Style Number/Barcode: 07302-0383

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Western Vibes Faux Leather Boots

    Home on the range in style wearing these faux leather boots! They feature a pointed toe, block heel, zipper closure, and smooth, faux leather exterior. Perfect for styling with skinny jeans.

    Fit & Features

    • Pointed toe
    • Block heel
    • Zipper closure
    • Knee-high length
    • Faux leather exterior
    • Runs true to size

    Style Number/Barcode: 07402-0322

    Category Name: Vacation Looks

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just My Type Knee-High Boots

    Your outfit of the day isn't complete without these knee-high boots! They feature a pointed toe, block heel, zipper closure, and smooth, faux leather exterior. Perfect for styling with a denim jacket.

    Fit & Features

    • Pointed toe
    • Block heel
    • Zipper closure
    • Knee-high length
    • Smooth faux leather exterior
    • Runs true to size

    Style Number/Barcode: 07402-0320

    Category Name: Vacation Looks

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Does It Faux Fur Slippers

    These faux fur slippers are total lounge goals! They feature double bands and a traction bottom. Perfect for styling with a cardigan.

    Fit & Features

    • Double bands
    • Faux fur 
    • Traction bottom
    • Runs true to size

    Style Number/Barcode: 07408-0083

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lazy Day Faux Sherpa Sandals

    Treat your feet to a day off with these cozy sandals! They feature ultra-soft faux sherpa and a traction bottom. Complete your look with leggings.

    Fit & Features

    • Faux sherpa 
    • Ultra-soft footbed
    • Traction sole
    • Runs true to size

    Style Number/Barcode: 07408-0086

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Cozy Slippers

    Treat your feet in cozy style with faux fur slippers! They feature double bands and a traction bottom with an ultra-soft sole. Style with a cozy loungewear set.

    Fit & Features

    • Double bands 
    • Faux fur 
    • Traction bottom
    • Runs true to size

    Style Number/Barcode: 07408-0085

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual And Cozy Chenille Sweater

    This adorable chenille knit sweater is casually chic and oh-so-cozy! It features a ribbed turtleneck, long dolman-style sleeves with cuffed hems, button detailing down the sides, and an oversized, relaxed fit. Pair this sweater with faux leather pants and booties.

    Fit & Features

    • Ribbed turtleneck
    • Long dolman sleeves, cuffed hems
    • Buttons down the sides
    • Chenille knit fabric
    • Oversized fit

    Style Number/Barcode: 06005-1073

    Category Name: Vacation Looks

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleek N' Chic Hoop Earrings

    Keep it chick with these classic, pink hoop earrings! The hoops have a sleek design that feature a rose gold shine an feature both an omega and post back closure for security.

    Style Number/Barcode: 07001-4042

    Category Name: Vacation Looks

    Price: $2.97 $5.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Chic Chandelier Rhinestone Earrings

    Bring the chic factor to your look with earrings that wow! The earrings feature a multi-row chevron design, mini rhinestones, and a drop coin design. Complete look with a bustier and mini skirt.

    Fit & Features

    • Multi-row chevron design
    • Mini rhinestones
    • Drop coin design 
    • Fish hook back 


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

    Style Number/Barcode: 07001-0936

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Vibes Leopard Print Cardigan

    Layer on the cozy vibes with this trendy leopard print cardigan. It features long sleeves, an open front, ribbed hems, and a relaxed and comfortable fit. The fuzzy knit fabric offers a moderate stretch. Style this cardigan with a basic tee and dark wash denim.

    Fit & Features

    • Long sleeves
    • Open front
    • Ribbed hems
    • Relaxed fit
    • Leopard print
    • Fuzzy knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1178

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Covetable Charm Strapless Mini Skater Dress

    From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.

    Fit & Features

    • Poplin stretchy fabric, sewn-in knit lining
    • Back zipper and hook-eye closure
    • Strapless square neckline
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3079

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Cozy Cable Knit Sweater

    Cozy on up in this adorable cable knit sweater! It features long blouson sleeves with tapered hems, a V-neckline with a trendy twist-front detail, a cute cable knit pattern, and a mid-length, relaxed fit. Style this sweater with dark wash denim and booties.

    Fit & Features

    • Long blouson sleeves, tapered hems
    • V-neckline
    • Twist front design
    • Cable knit pattern
    • Mid-length, relaxed fit
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1009

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Clear Must-Have Top Handle Bag

    This chic top handle bag is a clear must-have this season. It features a faux leather top handle strap, a fold-over design, a clear material with faux leather trim, and an included faux leather shoulder strap to convert the bag to a crossbody purse. Complete the look with strappy mules.

    Fit & Features

    • Faux leather top handle strap
    • Fold-over design
    • Clear material, faux leather trim
    • Included removable faux leather shoulder strap

    Style Number/Barcode: 07203-0841

    Category Name: Vacation Looks

    Price: $12.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Vibes High-Rise Skinny Jeans

    Bring the casual vibes to your everyday look with these high-rise skinny jeans. They feature a high-rise waist, a destructed detailing, and a skinny-leg fit that cuts off at the ankle. The medium-wash denim fabric offers a form hugging fit with minimal stretch. Style these jeans with a cute crop top and sneakers.

    Fit & Features

    • High-rise waist
    • Destructed detailing
    • Skinny-leg fit, ankle-cut hem
    • Medium wash denim fabric
    • Form hugging fit, minimal stretch, runs true to size
    • Traditional five-pocket and belt loop design
    • Front button and hidden zipper closure

    Style Number/Barcode: 06602-0331

    Category Name: Vacation Looks

    Price: $16.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Cute Lattice Back Sweater

    Style up this cozy cute cable knit sweater for the perf fall look! It features a wide crew neckline, long sleeves, an adorable lattice back detail, and a mid-length, relaxed fit. The cable knit fabric offers a moderate stretch and is super soft for comfortable wear. Complete the outfit with faux leather pants and booties.

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Lattice back, tie closure
    • Mid-length, relaxed fit
    • Cable knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1078

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance