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.

  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Edgy Stretch Resin Bracelet

    A little shine, a lot of style. This resin stretch bracelet with sleek metal trim is the low-effort way to elevate any outfit—stack it up or let it stand alone.

    Fit & Features

    • Smooth resin material
    • Stretch elastic fit
    • Polished metal trim accents
    • Lightweight and comfortable
    • Please note color varies

    Style Number/Barcode: 07003-000110

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Awaits Cutout Tropical Knit Jumpsuit

    This sexy cutout tropical knit jumpsuit is a definite must when packing for your trip to paradise! The stretchy lightweight knit fabric showcases an eye-catching palm leaf print perfect for your dream vacay. It features a sleeveless plunging neckline with cross-front spaghetti straps and a halter tie-back design for a customized fit. The alluring waist cutouts lead to an open lower back for added sultry flair. The hip-hugging fit flows down to a relaxed wide-leg silhouette. Complete the look with strappy sandals.

    Fit & Features

    • Tropical printed knit fabric, lined bust, plenty of stretch
    • Plunging neckline with cross-front spaghetti straps, halter tie-back design
    • Waist cutouts, open back
    • Hip-hugging fit
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2494

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style Knit Right Chenille Sweater

    You'll love styling this chenille crop sweater into your weekly outfit rotation! It features cozy long sleeves, a crew neck, and a striped color block pattern composed of a cable knit design. The ultra-soft chenille fabric has no stretch. Complete the look in boyfriend jeans for a cute and casual vibe!

    Fit & Features

    • Long sleeves
    • Crew neck
    • Striped color block pattern
    • Cropped hem
    • Cable knit design
    • Chenille fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1562

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • City Streets Slouch Stiletto Boots

    Walk down the city streets like it's your runway in these chic slouch stiletto boots! They feature an above-the-ankle height with a trendy slouched design, a pointed toe, and a sleek stiletto heel. Style with a crossbody bag.

    Fit & Features

    • Above-the-ankle height
    • Slouchy silhouette
    • Partial inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1592

    Category Name: Vacation Looks

    Price: $8.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Updated Chic High Rise Slit Linen Maxi Skirt

    Whether you're heading on vacation or out on the weekend, this linen maxi skirt will help you look chic all season! The high-rise waist and form-hugging fit flatter your figure while the adjustable front drawstring allows for a perfect fit. The high slit adds a touch of drama and the maxi-length hem exudes effortless style. Complete the look in a corset top and wedges.

    Fit & Features

    • Linen blend fabric, woven lining, no stretch
    • High-rise waist, side zipper and hook-eye closure
    • Adjustable front drawstring
    • High slit
    • Maxi-length, form-hugging
    • Runs true to size

    Style Number/Barcode: 06301-0188

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mixed Signals 50/50 Knee-High Boots

    Don't get your signals crossed, these knee-high boots are just what your closet needs! They feature an almond toe, low-block heel, side zipper, and are half faux suede and knit compression. Style with a chic handbag. 

    Fit & Features

    • Almond toe
    • Low-block heel
    • Side zipper
    • Knee-high length
    • Half faux suede, half knit compression
    • Runs true to size

    Style Number/Barcode: 07402-0696

    Category Name: Vacation Looks

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Play My Song Lace Fringe Crop Top

    Move to the music in this lace fringe crop top at festivals, concerts, or your fave country bar!

    Fit & Features

    • Lace fabric, bust knit lining
    • Strapless neckline
    • Sheer fitted crop hem, fringe trim
    • Runs true to size

    Style Number/Barcode: 06001-000105

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Energy Over The Knee Boots

    Embody a sleek fashion sense in these over-the-knee boots perfect for elevating your fit! They feature an almond toe, block heel, inner side zipper closure, and an adjustable drawcord. Complete the look in a trendy sweater dress.

    Fit & Feature

    • Almond toe
    • Block heel
    • inner side zipper closure
    • Over-the-knee length shaft
    • Adjustable drawcord
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0833

    Category Name: Vacation Looks

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Call The Shots High-Rise Wide-Leg Pants

    Decide your fashion direction in these high-rise pants for creating unique and stylish outfits! They feature a flattering high-rise waist and a breezy wide-leg silhouette for comfort and chicness. Style with a crop top, earrings, and wedges!

    Fit & Features

    • Woven fabric with minimal stretch
    • High-rise waist, back elastic band
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1395

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Making Waves Shell Claw Clip Set

    Not your average hair clip—these shell-shaped claws bring full glam to your grab-and-go moments. Whether you're throwing your hair up for errands or adding a little luxe to your vacation look.

    Fit & Features

    • Two-pack claw clip set
    • High-shine metal material
    • Seashell design

    Style Number/Barcode: 07006-000077

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let It Flow Crochet V-Neck Skater Dress

    Flowy and flirty! Twirl all day in this crochet V-neck skater dress featuring a sleeveless bodice with adjustable spaghetti straps, an open back with tie closure, and a tiered short hem. Composed of a gauze woven fabric with an inner lining. Finish the look in trendy mules.

    Fit & Features

    • Sleeveless bodice, crochet V-necklined
    • Adjustable spaghetti straps
    • Open-back, tie closure
    • Tiered short hem
    • Skater silhouette
    • Airy gauze woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4397

    Category Name: Vacation Looks

    Price: $21.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Linen Shorts

    Fall back on basic shorts with a stylish twist! These shorts are ready for warmer days with a high-rise waist, a tie-waist belt, a wide leg hem, and a back zipper closure for a secure fit. Complete look with a floral bodysuit and wedges for the perfect brunch outfit with the squad!

    Fit & Features

    • High-rise waist
    • Tie-waist belt
    • Wide leg hem
    • Back zipper closure
    • Lined linen fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06303-0150

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Day Dream Tie-Front Crop Top

    Look like a tropical day dream in this crop top while on vacation! The flowy long sleeves with banded cuffs ensure a comfortable fit, while the tie-front closure and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching pants and skirt.

    Shop Matching Pants: Tropical Day Dream High-Rise Wide Leg Pants
    Shop Matching Skirt: Tropical Day Dream High-Rise Wrap Mini Skirt

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Flowy long sleeves, banded cuffs
    • Tie-front closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-0451

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripe With It Halter Ribbed Knit Crop Top

    Own this striped knit crop top all season! It's perfect for flaunting your figure with a square halter neckline and fitted crop hem. The striped pattern on the ribbed knit fabric gives it a trendy vibe. Complete the look in denim shorts for a summer fair or BBQ.

    Fit & Features

    • Striped pattern
    • Stretchy ribbed knit fabric
    • Halter square neckline, tie closure
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-1994

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced-Up Masterpiece Floral Slit Maxi Dress

    Elevate your style with this stunning floral maxi dress that commands attention. The striking lace-up back adds an alluring touch, while the front slit reveals some skin along the form-hugging silhouette.

    Fit & Features

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

    Style Number/Barcode: 05101-4143

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Parisian Beauty Wool Beret

    Look and feel like a Parisian beauty accessorizing with this wool beret perfect for styling with a sleek crop blazer for a city-girl look.

    Fit & Features

    • Classic beret style
    • Wool material

    Style Number/Barcode: 07302-1347

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Fall Vibes Belted Plaid Shacket

    Layer on this trendy plaid flannel shacket for all the cozy fall vibes! It features a collared neckline, long sleeves, a complete button-down front, pockets, a tie-front belt to stylishly cinch your waist, and a relaxed fit. Pair with a basic bodysuit and a knit midi skirt.

    Fit & Features

    • Collared neckline, long sleeves, single button details
    • Button-down front
    • Buttoned chest pockets, faux side pockets
    • Tie-front belt
    • Relaxed fit
    • Plaid print, woven flannel fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1447

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soft Serve Floral Ruffle Tie-Front Top

    Serving soft with a wink. This sheer floral mesh top brings the flirt with ruffled edges, lace trim, and a tie-front that keeps things just bold enough. Perfect for date nights or casual slays.

    Shop Matching Skirt: Soft Serve Floral High Slit Maxi Skirt

    Fit & Features

    • Sheer mesh fabric, high stretch
    • Floral print
    • V-neckline with lace trim
    • Ruffled tie-front design
    • Long fitted sleeves
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000037

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Retreat Straw Envelope Clutch Crossbody Bag

    A straw clutch crossbody bag features a detachable wristlet strap, a front flap with snap-button closure, and a detachable shoulder strap for multiple styling options. Perfect for vacation retreats or summer styling.

    Fit & Features

    • Detachable wristlet strap
    • Front flap with snap-button closure
    • Detachable shoulder strap
    • Straw material

    Style Number/Barcode: 07203-2071

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Chic Over-The-Knee Boots

    These fitted over-the-knee boots are so effortlessly chic. They feature an almond-shaped toe, a block heel, and an inner zipper closure. The boots are composed of a half faux suede and half stretchy knit composition. Style with a sweater dress and a trendy boater hat.

    Fit & Features

    • Over-the-knee fitted design
    • Almond-shaped toe
    • Block heel
    • Partial inner zipper closure
    • Half faux suede and half stretchy knit composition
    • Runs true to size

    Style Number/Barcode: 07402-0812

    Category Name: Vacation Looks

    Price: $12.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Sweet Chiffon Halter Babydoll Dress

    You'll be feelin' sweet and chic in this airy chiffon mini dress featuring a halter cutout neckline and flowy babydoll silhouette. Perfect for pairing with pearl earrings.

    Fit & Features

    • Sheer chiffon fabric with woven lining, no stretch
    • Sleeveless halter neckline, V-cut bust
    • Adjustable spaghetti straps, partially open back
    • Flowy babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4035

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always In Plaid Woven Crop Shacket

    Don't be surprised if you find yourself wearing this plaid crop shacket on repeat! It features long sleeves with button cuffs, a collar neckline, a button-down placket, pockets, and a boyfriend silhouette. Complete the look in knee-high boots for a chic autumn outfit!

    Fit & Features

    • Long sleeves with button cuffs
    • Collar neckline
    • Button-down placket, pockets
    • Boyfriend silhouette
    • Cropped hem
    • Plaid pattern, flannel woven fabric
    • Fits true to size

    Style Number/Barcode: 06204-1454

    Category Name: Vacation Looks

    Price: $21.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Vacay Attitude V-Neck Floral Tropical Maxi Dress

    Book those tickets and pack a bag cause vacation is calling and this floral tropical maxi dress is ready to answer! Made from an airy floral tropical printed chiffon fabric with a short woven lining, this dress is perfect for summer days. Featuring spaghetti strap tassel ties and V-neckline, cutout sides add a touch of flirty fun, while the flowy maxi-length silhouette and front slit provide style. Complete the look with a straw tote bag and sandals!

    Fit & Features

    • Tropical floral print, chiffon fabric, short woven lining
    • Spaghetti strap tassel ties
    • V-neckline
    • Cutout sides
    • Front slit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3446

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale