Vacation Looks

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STYLE SPOTLIGHT

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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.

  • A Perfect Day Puff Espadrille Wedge Sandals

    From beach vacations to sunset cocktails, these wedge sandals are perfect for summer fun! Featuring a square toe and a unique woven puff strap, you'll stand out in style. The espadrille platform wedge sole and padded faux leather footbed add comfort and elevated trendiness. Complete the look with a chic purse.

    Fit & Features

    • 2" Wedge heel
    • Square toe
    • Woven puff strap
    • Espadrille platform sole
    • Padded faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07406-0358

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Structure Cuff Bracelet

    You'll obsess over the sleek structure of this trendy cuff bracelet! It features a teardrop-shaped overlapping design with a snap closure. Style with hoop earrings.

    Fit & Features

    • Teardrop-shaped overlapping design
    • Snap closure

    Style Number/Barcode: 07003-0557

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Best Times Doorknocker Earrings

    The best times start with the best accessories like these earrings! They feature a statement doorknocker design and a post-back closure. Complete the look in a bodycon dress for date night.

    Fit & Features

    • Dooknocker design
    • Post back closure

     

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

    Style Number/Barcode: 07001-2031

    Category Name: Vacation Looks

    Price: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destined For Love Lace-Up Short Skater Dress

    You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.

    Fit & Features

    • Burnout pattern, mesh fabric, tulle and stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Lace-up, back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3319

    Category Name: Vacation Looks

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart It Oversized Round Sunglasses

    You'll totally heart these trendy oversized round sunglasses! They feature a round shape with a sleek plastic frame and arms, the cutest heart-shaped cutout design accented on the arms, built-in nose pads for support, and tinted lenses. Style these shades with a charm necklace.

    Fit & Features

    • Oversized round-shape
    • Plastic frame and arms
    • Heart-shaped cutout design
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1081

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Breezy Straw Clutch Bag

    One bag, endless ways to wear it. This straw foldover clutch comes with a detachable wrist strap and crossbody strap, making it the ultimate grab-and-go sunny day accessory!

    Fit & Features

    • Front foldover flap with snap-button closure
    • Detachable faux leather wrist strap
    • Detachable faux leather crossbody strap
    • Top zipper closure
    • Spacious lined interior
    • Straw material

    Style Number/Barcode: 07203-000118

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Glamour Steps Rhinestone Strappy Flat Sandals

    Add glamour to your steps in these faux leather flat sandals showcasing a sparkling rhinestone embellished trim, round toe, and rhinestone-embellished strappy design with an adjustable ankle strap with buckle closure. Complete the look in a casual bodycon dress for a day out and about!

    Fit & Features

    • Flat sole
    • Faux leather material
    • Round toe
    • Rhinestone trim
    • Rhinestone embellished strappy design
    • Adjustable ankle strap, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1158

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Cool Contrast Trim Faux Leather Sneakers

    These faux leather sneakers are too cool for school! Kick back in these exclusive shoes featuring a round toe and lace-up placket for a perfect fit. A cool contrast trim for added style and a comfortable footbed and rubber insole. Complete the look with a zip-up hoodie for casual plans.

    Fit & Features

    • Round toe
    • Lace-up placket
    • Contrast trim
    • Comfortable footbed
    • Rubber insole
    • Runs true to size

    Style Number/Barcode: 07407-0225

    Category Name: Vacation Looks

    Price: $28.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Fit Strapless Faux Wrap-Front Romper

    This strapless romper will give you a chic fit with its faux wrap-front design and form-hugging silhouette. Style for happy hour with strappy mules.

    Fit & Features

    • Smooth woven fabric, partial knit lining, moderate stretch
    • Strapless straight neckline, no-slip strip, dart seams
    • Back zipper with hook-eye closure
    • High waist seam
    • Faux wrap-front mini-length overlay, short slit, fitted shorts
    • Romper in size small is 22" top hem to bottom hem with a 12" front rise and a 2" inseam
    • Runs true to size

    Style Number/Barcode: 06403-1105

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Scene Crew Neck Midi Dress

    Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.

    Fit & Features

    • Crew neck, short sleeves
    • Cutout waist, knot accent
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Smooth cotton knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5765

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Escape Lace-Up Tropical Midi Dress

    Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical print, lined knit fabric, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Asymmetric high-cut hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5564

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Western Showdown Etched Concho Belt

    Saddle up with this playful etched concho belt, featuring an adjustable lobster clasp closure. Wrangle up some Western vibes and complete the look in denim shorts for a festival or concert!

    Fit & Features

    • Etched concho belt
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1113

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Luxe Flair Woven Loop Satin Scarf

    Add a luxe flair to your spring and summer 'fits with this woven loop satin scarf! Designed with a silky satin material with a chic woven loop pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with chunky gold hoop earrings.

    Fit & Features

    • Non-stretch satin material
    • Woven loop pattern

    Style Number/Barcode: 07305-0491

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Pick Flower Detail Sunglasses

    Shade, but make it sweet. These sleek frame sunglasses get a playful twist with flower side details—your go-to pair for adding instant charm to sunny days.

    Fit & Features

    • Sleek metal frame design
    • Flower detail side accents on the arms
    • Tinted lenses
    • Rubber nose supports
    • 100% UV protection

    Style Number/Barcode: 07008-000098

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK, PINK, BROWN

    Available Size: NS

  • Sunny Vibes High Slit Woven Midi Skirt

    This airy woven midi skirt will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric with a mini-length lining, it features a high waist with the cutest tie detail, a high-cut side slit to showcase some leg, and a flowy slim-fit silhouette. Style with the matching crop top for a fabulous 'fit!

    Shop Matching Orange Top: Sunny Vibes Bow Back Woven Crop Top

    Fit & Features

    • Woven fabric with mini-length knit lining, minimal stretch
    • High-rise elasticized waist
    • Tie detail
    • High side slit
    • Flowy slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 06401-0651

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Breeze Chain Printed Satin Scarf

    Add a luxe flair to your spring and summer 'fits with this woven chain-printed satin scarf! Designed with a silky satin material with a chic woven chain pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with high-rise denim shorts.

    Fit & Features

    • Satin chain printed woven scarf
    • Multiple styling options

    Style Number/Barcode: 07305-0500

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing The Sun Banner Woven Satin Scarf

    Chase this sun banner silky woven scarf for the perfect look for your next sweet escape! Designed with a silky satin material with a chic sun banner pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with a sultry jumpsuit.

    Fit & Features

    • Sun banner print
    • Woven satin fabric
    • Multiple styling options

    Style Number/Barcode: 07305-0499

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free Riders Colored Stone Chain Belt

    Accessorize your ride with this statement western chain belt featuring unique colored stones, oval-shaped charms, and an adjustable lobster clasp closure to secure the style. Complete the look in a fitted mini dress.

    Fit & Features

    • Colored stones
    • Oval-shaped charms
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1146

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boardwalk Crop Denim Jacket

    Stroll the boardwalk before your sunset dinner in this streetwear-inspired crop denim jacket featuring long sleeves with buttoned cuffs, a collared neckline, four-button front closure, flap pockets, distressed accents, and a pull tab button closure along the hem. Complete the look in breezy wide-leg pants and a bodysuit.

    Fit & Features

    • Non-stretch denim fabric
    • Long sleeves, buttoned-cuffs, collared neckline
    • Four-button front closure
    • Flap pockets, buttons
    • Distressed accents
    • Pull tab button closure along crop hem
    • Runs true to size

    Style Number/Barcode: 06203-0540

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Double Trouble Snake Chain Lariat Necklace Set

    Two chains, one goal—steal the spotlight. This snake chain lariat necklace set is your new go-to for stacking drama and drip, whether you’re out for dinner or just feelin’ yourself in selfies.

    Fit & Features

    • Two-pack necklace set
    • Short snake chain
    • Longer snake chain, triangle-shaped center accent, long lariat design
    • Back lobster clasp closures with extenders

    Style Number/Barcode: 07002-000026

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Bold Simplicity Bodycon Maxi Skirt

    No frills, no fuss—just pure silhouette. The smooth look, bodycon fit, and maxi hem give you an effortlessly pulled-together look that’s timeless yet modern. Pair with the matching top.

    Shop The Matching Top: Bold Simplicity Crop Tank Top

    Fit & Features

    • Double-lined slinky knit stretchy fabric
    • Mid-rise waist
    • Side ruched seams
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000076

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Cubic Zirconia Studs Set

    Glam up your look with this cubic zirconia stud earrings set. This pack of six varying-sized studs gives you the option of how much bling you want to rock for the day. Perfect to dress up an everyday outfit to go run errands. Pair with a chic bodysuit and distressed denim and you'll be all ready to go!

    Fit & Features

    • Cubic zirconia
    • Post-back closures, rubber stoppers
    • Set of six studs

     

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

    Style Number/Barcode: 07001-3731

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • When Life Gives You Lemons Tote Bag

    Carry summer vibes everywhere with this canvas tote bag! This eye-catching canvas tote features a vibrant lemon print that adds a refreshing pop to any outfit while providing plenty of space for your must-haves.

    Fit & Features

    • Top handles
    • Lemon print design
    • Spacious interior
    • Canvas material

    Style Number/Barcode: 07203-000026

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ardell Demi Wispies Lashes 5 Pack

    Glam up your eyes with these gorgeous lashes. The Ardell Demi Wispies lashes offer a natural, long feathered and glamorous look, are easy to apply, and are even reusable! Perfect for your next sexy night out outfit like a sultry crop top and mini skirt. The lashes work best for large and deep-set eyes. Don't forget to pick up the eyelash glue! 

    Fit & Features

    • Long, feathered natural look
    • Reusable 
    • Includes 5 sets of eyelashes
    • Eyelash glue sold separately

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07307-0372

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free