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.

  • Island Flirt Floral Crop Top

    Serving vacation plans without the plane ticket. This tropical floral crop top features a draped cowl halter neckline and an open tie back that keeps things breezy and just a little extra.

    Fit & Features

    • Tropical floral print, mesh fabric, sewn-in knit lining
    • Cowl halter neckline, tie straps
    • Open tie back
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000558

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Lowkey Bold Strapless Ruffle Hem Mini Dress

    Not here to blend in—this one hugs, shapes, and makes an impression without trying. The strapless bodycon mini dress with a ruffle hem and sheer waist detail brings texture and dimension that feels just as good as it looks.

    Fit & Features

    • Textured knit fabric with partial knit lining, moderate stretch
    • Strapless straight-across neckline
    • Sheer waist insert
    • Mini-length tiered ruffled hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000305

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Hayden Floral Satin A-Line Formal Dress

    Special Occasion

    A study in effortless elegance, the Hayden floral satin A-line gown is made for the kind of entrance that lingers. Designed with a softly ruched bodice and fluid skirt, it moves with you—polished, poised, and undeniably captivating.

    Fit & Features

    • Floral pattern, satin fabric
    • Sweetheart strapless neckline
    • Tie-back detail
    • High front slit
    • A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, graduations, bridal celebrations, galas, upscale birthday events, fancy brunches, vacations, formal milestone parties, anniversaries, fashion-forward soirees

    Style Number/Barcode: 05002-001379

    Category Name: Vacation Looks

    Price: $99.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L, XL

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

    Special Occasion

    The Molly floral chiffon A-line gown moves like a dream with every step. The sweetheart strapless neckline and softly pleated skirt create a romantic silhouette that feels effortlessly elevated for any special occasion.

    Fit & Features

    • Paisley floral print, chiffon fabric, stretchy knit lining
    • Sweetheart neckline, padded bra cups
    • Keyhole bust cutout with tie
    • Mini lace-up back, open back, lower zipper and hook-eye closure
    • Pleated A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Destination and outdoor weddings, vacations, resort dinners, honeymoons, birthday soirees, summer cocktail parties, bridal showers, fashion-forward events

    Style Number/Barcode: 05002-001464

    Category Name: Vacation Looks

    Price: $129.90

    Availability: In Stock

    Available Color: WHITE, PRINT

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Styled Chic Button Halter Neck Mini Dress

    Serving sculpted and styled without trying too hard. This halter neck mini dress hugs your curves with a sleek ribbed feel and subtle button detail that keeps it chic from every angle.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Sleeveless V-neckline
    • Varied button accents
    • Halter strap, partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000316

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Island Escape Cutout Halter Jumpsuit

    Booked the vibe before the trip even starts. This tropical print jumpsuit brings the island muse with a beaded halter neckline and bold cutout that turns every step into a statement.

    Fit & Features

    • Tropical print, knit stretchy fabric
    • Halter neckline with tie straps
    • Front cutout design
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000096

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

  • Serving Sweet Lace Ruffle Skater Dress

    Caught feelings… for this dress. The sweet lace ruffle skater dress hugs up top then flares into playful tiers, perfect for parties, date nights, or any plan that needs a little extra attention.

    Fit & Features

    • Sheer lace fabric with lining, moderate stretch
    • Sleeveless sweetheart neckline
    • Twist-front bust design, small keyhole cutout
    • Adjustable spaghetti straps
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001098

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XXS, M, L

    Product Badge:
    • Best Seller
  • Sweet Style Polka Dot Mesh Romper With Scarf

    Sweet with a little edge. This polka dot mesh romper with a scarf accent hugs in all the right places, then flares into soft ruffles that move with you from plans to after plans.

    Fit & Features

    • Polka dot mesh fabric with knit lining, high stretch
    • Sleeveless straight-across neckline, 
    • Drop waist seam
    • Tiered ruffled design
    • Mini-length overlay, fitted A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000303

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Flirt In Motion Chiffon A-Line Mini Dress

    This one just RSVP’d yes to every plan on your calendar. The flirty, flowy chiffon A-line mini dress brings that barely-there feel with a statement open back that keeps all eyes on you.

    Fit & Features

    • Sheer chiffon fabric with lining
    • Sleeveless halter neckline
    • Halter tie-back spaghetti straps
    • Open back, lower zipper closure
    • Mini-length asymmetric hem
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001132

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK, BLUE

    Available Size: XS, S, M, L, XXS

    Product Badge:
    • Best Seller
  • Make Plans Eyelet Ruffle Mini Dress

    Last-minute plans just got a major upgrade. This eyelet ruffle mini dress hugs through the bodice with a flirty drop waist and tiered skirt that’s made for showing up and standing out.

    Fit & Features

    • Eyelet knit fabric with knit lining, high stretch
    • Strapless straight-across neckline
    • Fitted bodice, ruched detailing
    • Drop waist seam
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000715

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Dressed For The Moment Halter Mini

    This dress keeps it simple, but never forgettable. The textured fabric hugs just right while the halter neckline and open back add a confident allure, fitting perfectly into your suitcase for vacay!

    Fit & Features

    • Textured sweater knit fabric
    • Halter V-neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000329

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Sunday In Bloom Strapless Midi Dress

    This midi dress feels like a soft yes to every pretty plan on your calendar. The delicate floral print, smocked bodice, and flowy silhouette make it perfect for vacations, brunch, or any sunny day plans.

    Fit & Features

    • Floral borderprint, cotton woven fabric, smooth woven lining
    • Strapless smocked bodice with stretch
    • Back zipper and hook-eye closure
    • Flowy A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000798

    Category Name: Vacation Looks

    Price: $72.90

    Availability: In Stock

    Available Color: BLUE, PINK

    Available Size: S, M, L

  • Escape The City Metallic Wedges

    These metallic wedge sandals bring vacay energy with a glossy metallic finish and adjustable ankle strap—made for sunset dinners, beachside strolls, and weekend trips.

    Fit & Features

    • 4.5" wedge heel
    • Almond toe
    • Clear PVC toe strap
    • Adjustable ankle strap with buckle closure
    • Cushioned footbed
    • Espadrille and metallic material
    • Runs true to size

    Style Number/Barcode: 07406-000052

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: GOLD

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

  • Coastal Plans Espadrille Wedges

    Your outfit just found its finishing touch. These espadrille wedges give you that effortless lift with an H-shaped band design and a sleek faux leather footbed that elevates your weekend or vacay lineup.

    Fit & Features

    • 4.5" wedge heel
    • Square toe
    • H-shaped band design
    • Adjustable ankle strap with buckle closure
    • Faux leather footbed
    • Espadrille sole
    • Runs true to size

    Style Number/Barcode: 07406-000051

    Category Name: Vacation Looks

    Price: $35.90

    Availability: In Stock

    Available Color: BLACK, GOLD

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

  • City Stroll Gingham Shorts

    First stop coffee, next stop wherever the day takes you. These gingham shorts are fitted through the waist, with a smocked feel and a flirty finish that make them an easy pick for laid-back plans or styled-up moments.

    Shop Matching Top: City Stroll Gingham Halter Crop Top

    Fit & Features

    • Lightweight woven fabrication
    • Mid-rise waist
    • Gingham pattern
    • Ruffled hem
    • Cheeky fit
    • Runs true to size

    Style Number/Barcode: 06303-000053

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sweet Day Plans Eyelet Open Back Mini Dress

    Made for sunlit tables, pretty plates, and plans that start early and linger. This A-line mini dress features eyelet lace detailing and an open back, perfect for showers, graduations, and every daytime soiree.

    Fit & Features

    • Eyelet lace cotton woven fabric, stretchy knit lining
    • Scoop neckline with trim
    • Adjustable spaghetti straps
    • Open back, stretchy smocked panel, hidden zipper and hook-eye closure
    • Voluminous A-line silhouette
    • Eyelet lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001021

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Play Nice Ruffle Romper

    Spark your inner flirt in this ruffle romper designed with an open back moment and draped side ruffle sashes that move with you from day to night.

    Fit & Features

    • Smooth knit stretch fabric, sewn-in panty lining
    • Halter V-neckline, tie straps
    • Open back
    • Fitted bodice
    • Layered tier ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06503-000284

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Back For More Halter Mini Dress

    All eyes on you always. This knit mini dress hugs your shape with side ruching and an open-back moment that keeps the focus on you.

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • High halter neckline with tie straps
    • Open back, adjustable strap
    • Side ruched seams
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000419

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: LAVENDER

    Available Size: M, L

  • Soft Focus Floral Halter Skater Mini Dress

    Plans pending, outfit already decided. This halter mini dress cinches you in with soft ruching and flows into tiered ruffles that move with every step, perfect for brunch dates, park hangs, and last-minute plans.

    Fit & Features

    • Lined mesh and lace fabrication
    • Sleeveless halter neckline with adjustable neck tie
    • Ruched bodice, back zipper and hook-eye closure
    • Floral pattern
    • Tiered ruffled skater silhouette
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05101-001094

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Flirt Mode Ruffle Sleeve Tie-Front Top

    A little sweet, a little bold—this one knows exactly what it’s doing. The tie-front top hugs in all the right places with ruffle sleeve detail that keeps it playful from brunch plans to late dinners. Style with the matching mini skort.

    Shop Matching Bottoms: Flirt Mode Ruffle Mini Skort

    Fit & Features

    • Sleek knit fabric, high stretch
    • V-neckline
    • Tie-front design
    • Short ruffle sleeves
    • Ultra-cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06202-000107

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Threaded Romance Tie-Front Duster

    This sheer gauze maxi duster drapes effortlessly with delicate floral embroidery and dual tie-front details that elevate anything underneath in seconds.

    Fit & Features

    • Sheer gauze woven fabric
    • Dual tie-front
    • Sleeveless design
    • Sheer embroidered mesh waist inserts
    • Floral embroidery detailing
    • Breezy long-length hemline
    • Runs true to size

    Style Number/Barcode: 06204-000133

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Late Dinner Plans Tube Maxi Dress

    This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.

    Fit & Features

    • Soft jersey knit fabric, stretchy lining
    • Strapless tube neckline, non-slip grip lining
    • Ruched fitted bodice
    • Flowy curve-hugging silhouette
    • Shark-cut maxi hem
    • Runs true to size

    Style Number/Barcode: 05102-000787

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

  • Resort Days Slide Sandals

    Straight to the vacation outfit rotation. These slide sandals keep things clean and elevated, perfect for beachside brunches, souvenir shopping, and everything in your daytime lineup.

    Fit & Features

    • Square toe
    • H-shaped band
    • Cushioned insole
    • Flat sole
    • Metallic/faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000053

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: GOLD

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

    Product Badge:
    • Best Seller
  • Poolside Ready Starfish Strap Sandals

    Booked, busy, and beach-bound—these are coming with you. Designed with a cushioned insole and starfish accent, these thong strap flat sandals keep every step cute from pool days to weekend escapes.

    Fit & Features

    • Almond toe
    • Thong toe strap with starfish accent
    • Luxe fit cushioned insole
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000070

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: BROWN

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

    Product Badge:
    • Best Seller