Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • The Lone Star Distressed Straw Cowboy Hat

    A straw cowboy hat features a distressed wide curved brim with rope trim and an adjustable rope to get a snug fit. Style with cowboy boots for a concert.

    Fit & Features

    • Distressed wide curved brim, rope trim
    • Adjustable inside rope
    • Straw material

    Style Number/Barcode: 07302-1703

    Category Name: Vacation Looks

    Price: $2.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Wide Leg Pants Energy

    She’s luxe, bold, and lowkey lethal. These tropical wide-leg pants brings the heat wherever you wear her—beach club or rooftop takeover. Pair with the matching top.

    Shop Matching Top: Golden Hour Tube Top Energy

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Mid-rise waist
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000032

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Edgy Chain-Link Bracelet

    Upgrade your outfit with this edgy bracelet! This bold bracelet features multiple chain links for a unique and eye-catching look. Style with a strapless jumpsuit for a cute and trendy look!

    Fit & Features

    • Multiple chain-link design
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07003-0562

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Babe Straw Cowboy Hat

    Add a cute western vibe to your beachy looks with this straw cowboy hat featuring a woven design, braided rope center accent, and long chin strap with a beaded detail.

    Fit & Features

    • Straw material
    • Woven design
    • Structured top
    • Wide curved brim
    • Braided rope center accent
    • Long chin strap with beaded detail

    Style Number/Barcode: 07302-000073

    Category Name: Vacation Looks

    Price: $25.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Looking Like A Dream High-Rise Ponte Skort

    Make weekend styling simple with this ponte skort! Designed with a flattering high-rise waist and sleek side slits, this form-hugging skort offers both comfort and a chic silhouette. 

    Fit & Features

    • Ponte fabric, moderate stretch
    • High-rise waist
    • Side slits
    • Form-hugging fit
    • Skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000065

    Category Name: Vacation Looks

    Price: $27.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Trendy Deets Stud And Hoop Earrings Set

    You'll obsess over the trendy deets of this stud and hoop earrings set! The multi-pack features six pairs of varying earrings, including circular studs, rhinestone studs, sleek bar studs, classic huggie hoops, bar studs with hanging chain design, and chic cross-front rhinestone hoops. Include post-back closures. Style with a layered charm necklace.

    Fit & Features

    • Six-pack earrings set
    • Circular studs, rhinestone studs, bar studs
    • Huggie hoops
    • Bar studs with hanging chain detail
    • Cross-front rhinestone hoops
    • Omega closure, post-back closures, rubber stoppers

     

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

    Style Number/Barcode: 07001-1974

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In the Loop Chain Necklace

    Serving sleek, chic, and totally on repeat—this one goes with everything. The interlocked design adds texture and edge, perfect for layering or letting it shine on its own.

    Fit & Features

    • High-shine metal finish
    • Interlocked chain-link design
    • Back lobster clasp closure with extender

    Style Number/Barcode: 07002-000025

    Category Name: Vacation Looks

    Price: $13.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Summer Mood Floral Crochet Sandals

    These floral crochet sandals will put you in the mood for cute summer styling! Designed with a synthetic faux leather upper, they feature an open round toe, a wide banded strap with an adorable floral crochet design in bright hues, and a flat sole. The open back offers effortless on-and-off styling. Pair these sandals with a charm necklace and aviator sunglasses!

    Fit & Features

    • Synthetic faux leather upper
    • Open round toe
    • Single banded strap
    • Multi-colored floral crochet design
    • Open back, flat sole
    • On-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1184

    Category Name: Vacation Looks

    Price: $20.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Finishing Touch Woven Shoulder Bag

    Put the perfect finishing touch to your look with this woven shoulder bag! With versatile styling options and a secure magnetic closure, you'll adore this bag all spring and summer.

    Fit & Features

    • Top shoulder strap
    • Detachable crossbody strap
    • Front flap with magnetic closure
    • Spacious interior
    • Woven faux leather material

    Style Number/Barcode: 07203-2130

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: NS

  • Rodeo Aesthetic Western Concho Belt

    Cinch together your western look with this concho belt featuring square shapes with colored stones on a chain with a secure lobster clasp closure. Perfect for styling with cowboy boots.

    Fit & Features

    • Square shapes with colored stones
    • Chain
    • Lobster clasp closure

    Style Number/Barcode: 07301-0674

    Category Name: Vacation Looks

    Price: $2.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Eyes Only Slide Sandals

    These comfy-cute slides feature a clear strap topped with a bold heart charm—perfect for pool days, park hangs, or running errands like a style icon.

    Fit & Features

    • Round toe
    • Clear PVC strap with heart cutout
    • Comfortable footbed
    • Platform sole
    • Runs true to size

    Style Number/Barcode: 07404-000005

    Category Name: Vacation Looks

    Price: $20.90

    Availability: In Stock

    Available Color: CLEAR

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Style On Point Cat-Eye Sunglasses

    These cat-eye sunglasses are here to make sure your style is always on point! They feature tinted lenses and a comfortable fit. Complete the look with a denim jacket and sandals!

    Fit & Features

    • Cat-eye silhouette
    • Tinted lenses
    • Comfortable fit

    Style Number/Barcode: 07008-1086

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Big Mood Tortoiseshell Oversized Sunglasses

    Giving off that “who is she?” energy in the best way. These oversized sunglasses bring effortless cool to your sunny day 'fits, from pool hangs to city strolls.

    Fit & Features

    • Oversized square-shaped design
    • Tortoiseshell thin metal frame
    • Thin arms
    • Flexible rubber nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000051

    Category Name: Vacation Looks

    Price: $11.90

    Availability: In Stock

    Available Color: TORTOISE

    Available Size: NS

  • Cool Living Aviator Sunglasses

    A pair of cool aviator sunglasses featuring a sleek metal frame, smokey tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.

    Fit & Features

    • Sleek metal frame
    • Smokey tinted lenses
    • 100% UV protection
    • Rubber nose supports

    Style Number/Barcode: 07008-1103

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Western Life Colored Stone Concho Chain Belt

    A statement concho chain belt features textured squares with colored stones and an adjustable lobster clasp closure. Style with a denim short dress and boots.

    Fit & Features

    • Textured squares with colored stones
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1192

    Category Name: Vacation Looks

    Price: $2.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shell We Dance Crochet Hanky Top

    Your boho era just called and said to wear this. This crochet hanky top brings flirty vibes with a strapless fit and fringe shell trim, perfect for beach days, brunch dates, or dancing barefoot in the sand.

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Strapless tube neckline
    • Hanky hem with shell trim
    • Runs true to size

    Style Number/Barcode: 06005-000080

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sunset Drinks Platform Block Heels

    These fab platform block heels were made to be worn while sipping on some drinks at sunset! They feature an open almond-shaped toe with an adorable knotted toe strap design, a thin adjustable ankle strap with a buckle closure, a closed back, a tall platform sole, and a chunky block heel. Style with your fave summer dress for happy hour!

    Fit & Features

    • 5" Block heel
    • Open almond toe, knotted toe strap design
    • Adjustable ankle strap with buckle closure, closed back
    • Platform sole, padded faux leather insole
    • Natural heels are woven material with a metallic threaded design
    • Denim heels are denim material
    • Runs true to size

    Style Number/Barcode: 07401-4857

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave V-Cut Bikini Bottoms

    Bring the heat to your summer vacay in these bikini bottoms featuring a high V-cut waist and cheeky fit. Pair with the matching bikini top.

    Shop Matching Top: Heat Wave Halter Bandeau Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • High V-cut waist
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000007

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed Strapless Ruffled Woven Skater Romper

    They'll be oh-so-charmed by you in this flirty ruffled woven skater romper! Designed with a breezy woven fabric, it features a strapless straight-across neckline, flexible boning at the bodice for added structure, a tie-back design for a stylishly cinched waist, an adorable short ruffled overlay over flowy shorts, and a fit-and-flare silhouette. Complete your look with hoop earrings and sneakers for a cute and casual vibe.

    Fit & Features

    • Woven fabric, stretchy knit lining
    • Strapless straight neckline, flexible boning
    • Tie-back design
    • Back zipper with hook-eye closure
    • Ruffled overlay, flowy shorts
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 06403-0400

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hello Summer Triangle Bikini Top

    Say hello to summer in this trendy bikini top featuring triangle-shaped cups with removable padding and dual spaghetti strap ties that let you customize the style. Pair with the matching bikini bottoms for a pool party.

    Shop Matching Bottoms: Hello Summer V-Cut Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Triangle design
    • Removable padding
    • Dual tie-back halter straps
    • Lower tie-back straps
    • Runs true to size

    Style Number/Barcode: 07104-000008

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, SLATE

    Available Size: L, M

    Product Badge:
    • Sale
  • Gleam Always Snake Chain Necklace

    Always gleam in this essential snake chain necklace to give every outfit the perfect accessory! Complete the look in a bodycon dress for any occasion. 

    Fit & Features

    • Snake chain
    • Back adjustable chain with clasp closure

    Style Number/Barcode: 07002-1817

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel The Vibes Halter V-Neck Crop Top

    Get ready to feel the vibes of this elevated basic halter V-neck crop top! It's perfect for styling with any bottoms.

    Fit & Features

    • Smooth knit, cotton-blend, stretchy fabric
    • Halter V-neck
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000206

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: GREEN, OFF, WHITE, BLACK, DARK, DENIM, BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Eyes On Me Cat Eye Sunglasses

    Catch their gaze and keep it—these cat eyes were made for golden hour snaps and spontaneous weekend plans. Lightweight with just enough edge to own the moment.

    Fit & Features

    • Metal frame with sleek cat eye silhouette
    • Adjustable nose pads
    • Slim arms with subtle curve
    • Gradient lenses 

    Style Number/Barcode: 07008-000045

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • Sunny Fave Espadrille Platform Wedges

    These adorable espadrille platform wedges will be a new fave for sunny weekend plans! With the trendy square toe and thin strappy design, you'll love styling them with your brunch dresses.

    Fit & Features

    • 4" Espadrille wedge heel
    • Open square toe
    • Asymmetric strappy design
    • Adjustable ankle strap with buckle detail
    • Platform design
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07406-0363

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 8, 8.5