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.

  • Vacation Pending Drop Hoop Earrings

    The kind of drop hoop earrings that make every outfit look like it came with a boarding pass. Lightweight with a statement shape, they’re made for rooftop dinners, beach clubs, and last-minute “wait, where’d you get those?” texts.

    Fit & Features

    • Resin material
    • Round stud
    • Rectangle accent
    • Drop hoop design
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000424

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Statement Step Snake Wedges

    Minimal up top, a little extra lift underneath. These wedge sandals keep it sleek with a clear strap and a sassy snake pattern that works from day plans to last-minute nights out.

    Fit & Features

    • 3" wedge heel
    • Round toe
    • Clear PVC thong toe strap
    • Luxe fit cushioned insole
    • Snake pattern, faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-000036

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: SNAKE

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

  • Sunset Stacks Bangle Bracelet Set

    Stacked up and impossible to ignore. This two-pack bangle bracelet set mixes a textured metal bangle with an asymmetric acrylic shape for the kind of effortless finishing touch that makes every outfit feel a little more styled.

    Fit & Features

    • Two-pack bangle bracelet set
    • Textured metal bangle
    • Asymmetric acrylic bangle

    Style Number/Barcode: 07003-000239

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: NS

  • Postcard Crush Floral Corset Top

    Pretty enough for vacation photos. This lace-up corset top effortlessly sculpts your figure with flexible boning inserts, while the crop hem makes it stylish with any bottoms.

    Fit & Features

    • Tropical print, mesh fabric, sewn-in knit lining
    • Tube strapless neckline, non-slip grip lining
    • Side zipper and hook-eye closure
    • Lace-up back placket
    • Flexible boning inserts
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000555

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Desert Trend Straw Cowboy Hat

    A little country, a little poolside, and fully committed to the outfit. The colored stone detail and embroidered band give it a unique, western aesthetic to any outfit.

    Fit & Features

    • Structured cowboy hat silhouette
    • Embroidered band, colored stone, tie-back
    • Contrast trim throughout
    • Wide curved brim

    Style Number/Barcode: 07302-000293

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: TAN

    Available Size: NS

  • Vintage Coded Two Pack Bangle Bracelets

    This two-pack bangle bracelet set gives effortless summer energy like you just got back from somewhere coastal with too many photos to post.

    Fit & Features

    • Two-pack bangle bracelet set
    • Chunky design

    Style Number/Barcode: 07003-000329

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Maryanne Floral A-Line Formal Dress

    Special Occasion

    The Maryanna A-line dress brings effortless drama with every step. This satin column gown features an oversized floral print, a sleek halter neckline with hardware detail, and an open-back silhouette that's striking and bold.

    Fit & Features

    • Statement floral print, premium satin fabric, stretch knit lining
    • Halter neckline with hardware insert, tie strap
    • Open tie-back, lower zipper and hook-eye closure
    • A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Outdoor weddings, vacations, honeymoons, resorts, cocktail parties, birthday dinners, milestone celebrations, summer date nights

    Style Number/Barcode: 05002-000961

    Category Name: Vacation Looks

    Price: $74.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Shell Yeah Wide-Leg Pants

    Planned the outfit before the trip. These slinky knit wide-leg pants bring easy movement and extra drama with a layered chain swag belt finished in seashell and faux pearl charms that do all the styling.

    Fit & Features

    • Slinky knit stretchy fabric
    • Mid-rise waist, mini ruched side seams
    • Layered swag chain belt detail, seashell and faux pearl charms
    • Lobster clasp closures
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000101

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Oceanside Kiss Open Back Midi Dress

    This halter midi dress hugs in all the right places with a plunging neckline, ruched waist, and open back made for dinners, vacations, and every occasion that calls for extra attention.

    Fit & Features

    • Floral print, knit stretchy fabric, lined
    • Plunge halter neckline, tie strap
    • Open back
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001130

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Island Attention Floral Tube Mini Dress

    Booked the trip just to wear this dress. The bold tropical floral print and bodycon silhouette will make heads turn at the beach clubs, island resort, or a weekend pool party!

    Fit & Features

    • Statement floral print, knit-lined stretchy fabric
    • Strapless tube neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000751

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Cherry On Top Eyelet Romper

    Caught flirting with the dress code again. This eyelet romper brings the charm with puff sleeves, a cinched fit, and the kind of open back detail that gets a second look at brunch, birthdays, and vacations.

    Fit & Features

    • Eyelet woven fabric, sewn-in woven lining
    • Sweetheart neckline, tie bust, padded bra cups
    • Short puff sleeves
    • Open back, lower zipper and hook-eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06303-000049

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Postcards And Plans Satin Mini Dress

    Serving vacation looks. The silky print dress boasts an open back detail, making this dress feel straight out of a suitcase packed for a European trip or sunny getaway.

    Fit & Features

    • Multi-print design, silky satin fabric, woven lining
    • Strapless tube neckline, non-slip grip lining
    • Side zipper and hook-eye closure
    • Cutout open back detail with hook closure strap
    • Curve-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001070

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M

  • Weekend In Soho Round Sunglasses

    These sunglasses give every outfit a stylish finish. The slim, rounded rectangle shape and tortoise finish give off cool café in the city energy.

    Fit & Features

    • Rounded rectangle shape
    • Slim design
    • Tortoise pattern
    • Tinted lenses

    Style Number/Barcode: 07008-000129

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: TORTOISE

    Available Size: NS

  • Too Busy Round Sunglasses

    These sleek sunglasses give quiet confidence. The slim silhouette and dark lenses make every outfit feel a little more polished, whether you’re headed to brunch, boarding a flight, or avoiding eye contact in style.

    Fit & Features

    • Round slim silhouette
    • Tinted lenses
    • Hardware insert

    Style Number/Barcode: 07008-000130

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • Sunset Stroll Lace-Up Espadrille Wedges

    These wedges were made for sunset strolls after dinner. The lace-up straps, woven platform, and hoop detail give effortless vacation allure, whether you're on a getaway or staycation.

    Fit & Features

    • Almond toe
    • Strappy toe with hoop detail
    • Espadrille platform sole
    • Lace-up ankle straps
    • Runs true to size

    Style Number/Barcode: 07406-000068

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: TAN, BLACK

    Available Size: 8, 8.5, 9, 10, 11

  • Sunset Route Crochet Poncho

    This sheer crochet poncho layers perfectly over swimwear, bridal weekend looks, or sunset dinner plans with an asymmetrical neckline and hem that keeps the whole vibe easy and elevated.

    Fit & Features

    • Crochet cotton-blend woven fabric
    • Asymmetrical neckline
    • Flowy crop-length asymmetrical hem
    • Runs true to size

    Style Number/Barcode: 06204-000176

    Category Name: Vacation Looks

    Price: $19.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mireille Leopard Chiffon Formal Dress

    Special Occasion

    The Mireille floor-length gown brings effortless drama to every RSVP. Designed in airy chiffon fabric with a leopard print, this A-line dress features a plunging neckline, strappy open tie back, and high front slit that moves beautifully from cocktail hour to the dance floor.

    Fit & Features

    • Leopard print, chiffon fabric, mesh lining
    • Plunge halter neckline with bar accent
    • Open back with detachable beaded chain, zipper and hook-eye closure
    • Side waist cutout, hardware insert
    • High front slit
    • Flowy A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, engagement parties, vacations, honeymoons, destination celebrations, birthday dinners, cocktail soirees, and fashion-forward events.

    Style Number/Barcode: 05002-001317

    Category Name: Vacation Looks

    Price: $129.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Palm Springs Bound Satin Mini Dress

    This mini dress is bound for somewhere sunny. The satin finish, open back tie detail, and oversized floral print bring instant vacation drama in the best way possible. Just add sandals to complete the look.

    Fit & Features

    • Statement tropical floral print, satin fabric, knit lining
    • Halter neckline with tie straps
    • Open back with tie strap, zipper and hook-eye closure
    • Form-hugging silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001219

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Jennie Satin A-Line Lace-Up Formal Dress

    Special Occasion

    Jennie satin A-line gown skims the body before flowing into a soft, sweeping hem. The lace-up back and cascading ruffle detail bring just the right amount of drama—perfect for when you want to feel polished yet a little undone, in the best way.

    Fit & Features

    • Premium satin fabric, woven lining
    • Cowl neckline, spaghetti straps
    • Hidden side zipper and hook-eye closure
    • Lace-up open back
    • High front ruffled slit
    • A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, wedding guests, bridesmaids, black tie galas, formal milestone celebrations, engagement parties, destination events, anniversaries, big birthday parties, fancy showers

    Style Number/Barcode: 05002-000894

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, L, XL

    Product Badge:
    • Best Seller
  • Caught Staring Cat-Eye Sunglasses

    Caught staring? Understandable. These cat-eye sunglasses sharpen up any outfit with sleek metal accents and tinted lenses that do all the talking.

    Fit & Features

    • Cat-eye design
    • Plastic frame
    • Built-in nose pads
    • Thin metal arms, metal accents
    • Tinted lenses

    Style Number/Barcode: 07008-000133

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • Caught A Glance Oval Sunglasses

    These oval sunglasses bring that effortlessly trendy vibe to every outfit, whether you’re styling them with a baby tee and denim or throwing them on for a last-minute coffee run.

    Fit & Features

    • Long oval design
    • Thin metal frame
    • Flexible rubber nose pads
    • Wide arms
    • Tinted lenses

    Style Number/Barcode: 07008-000132

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Sleek Edge Shield Sunglasses

    Not here to blend in, and it shows. These shield sunglasses bring a sleek wrap-around fit with just enough edge to elevate your off-duty looks or last-minute plans.

    Fit & Features

    • Plastic curved wrap-around design
    • Shield-style silhouette
    • Wide arms, gold metal accent
    • Adjustable rubber nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000253

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: CLEAR, BROWN

    Available Size: NS

  • Trendy Shine Clear Bangle Bracelet

    The kind of accessory that makes your iced coffee and mirror selfies look instantly more on-trend. This clear acrylic bangle bracelet adds a sculptural finish to even the simplest outfit, whether you’re stacking it or letting it steal the attention solo.

    Fit & Features

    • Clear acrylic material
    • Chunky bangle bracelet silhouette
    • Faceted asymmetric design

    Style Number/Barcode: 07003-000250

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: CLEAR

    Available Size: NS

  • Tropical Soiree Flower Earrings

    These earrings feel like they belong with a sunset dinner reservation. The glossy orchid design adds the perfect pop of color to pull the whole vacation mood together.

    Fit & Features

    • Flower orchid design 

     

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

    Style Number/Barcode: 07001-000347

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: NS