Vacation Looks

HomeVacation Looks
Loading...

Now Trending

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.

  • Wild Bloom Leopard And Floral Print Tube Top

    Soft florals meet a little edge—because your outfits should never pick just one vibe. This leopard and floral print mesh tube top hugs your curves and instantly elevates your look. Style with the matching capri pants.

    Shop Matching Bottoms: Wild Bloom Leopard And Floral Print Carpi Pants

    Fit & Features

    • Mesh fabric with high stretch
    • Leopard and floral multi-print
    • Strapless straight-across neckline
    • Ruffle trim overlay
    • Cropped hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000510

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Wild Bloom Leopard And Floral Print Carpi Pants

    Soft florals meet a little edge—because your outfits should never pick just one vibe. These leopard and floral print mesh capri pants hug your curves and instantly elevate your look. Style with the matching tube top.

    Shop Matching Top: Wild Bloom Leopard And Floral Print Tube Top

    Fit & Features

    • Mesh fabric with high stretch
    • Leopard and floral multi-print
    • High-rise waist
    • Form-hugging fit
    • Capri-length silhouette, side slit detail
    • Runs true to size

    Style Number/Barcode: 06502-000080

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Liana Floral Print Beaded Sequin Mini Tube Dress

    Special Occasion

    Made for that moment when the night is just getting started, and all eyes are already on you, the Liana floral print mini tube dress brings shimmer and allure. The sleek, body-hugging silhouette and strapless neckline feel effortlessly sultry, while the intricate beading and sequins add a shine that moves with you.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • All-over beading and sequin embroidery
    • Strapless straight-across neckline, padded bra cups
    • Back metal bar closure, lower back cutout
    • Mini-length bodycon silhouette
    • Runs true to size

     

    Where to Wear:

    Birthday celebrations, bachelorette parties, vacations, date nights, sunset dinners, and glam nights out.

    Style Number/Barcode: 05001-000660

    Category Name: Vacation Looks

    Price: $99.90

    Availability: In Stock

    Available Color: PINK

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

    Product Badge:
    • Ships Free
  • Everyday Elevated Thong Sandals

    The sandals you'll be reaching for to complete any look. These flip flops keep it sleek and elevated with a cushioned sole that goes from errands to casual plans.

    Fit & Features

    • Square toe
    • Thong strap
    • Flat sole
    • Luxe fit cushioned insole
    • Smooth faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000048

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacation Booked Floral Maxi Dress

    Already picturing the dinner plans in this one. This tropical floral maxi dress features a soft cowl neckline and an open back that brings just the right amount of drama for your getaway lineup.

    Fit & Features

    • Tropical floral print, mesh-lined fabric, high stretch
    • Cowl neckline
    • Adjustable spaghetti straps
    • Open strappy back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000189

    Category Name: Vacation Looks

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make An Entrance Maxi Dress

    With its sultry cowl neckline, bold mixed print, and curve-skimming fit, this maxi dress was made for cocktail parties and dressed-up plans. Just heels and let the compliments follow!

    Fit & Features

    • Mixed animal and floral print, knit-lined fabric
    • Cowl halter neckline
    • Open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000802

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

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

  • Sunset Crush Floral Halter Top

    This halter top is made for vacation plans and last-minute “where are we going?” texts. The soft floral print and plunging halter neckline keep it flirty, while the ruched fit does all the work for you. 

    Fit & Features

    • Tropical floral print, stretchy knit fabric
    • Halter neckline
    • Side ruched seams
    • Form-hugging fit
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000630

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BANANA

    Available Size: M, L, XL

  • Vacation Mode Straw Clutch

    Booked, busy, and carrying this straw clutch. It keeps your look effortless with a chic twist clasp and a detachable chain strap for versatile styling! Perfect for complementing your getaway or weekend plans.

    Fit & Features

    • Front flap with hardware twist-turn closure
    • Detachable chain strap
    • Spacious-lined interior, three open compartments
    • Straw material
    • Versatile styling options

    Style Number/Barcode: 07203-000147

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

  • Soft Glow Floral Print Mesh Mini Skirt

    Caught in your softest glow—this floral print mesh mini skirt does all the flirting for you. It has a lightweight, curve-hugging feel, perfect for nights out or styled low-key. Pair with the matching tube top.

    Shop Matching Top: Soft Glow Floral Print Mesh Tube Top

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, high stretch
    • Large floral print on the front
    • High-rise waist
    • Mini-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000130

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Soft Glow Floral Print Mesh Tube Top

    Caught in your softest glow—this floral print mesh tube top does all the flirting for you. It has a lightweight, curve-hugging feel, perfect for nights out or styled low-key. Pair with the matching mini skirt.

    Shop Matching Bottoms: Soft Glow Floral Print Mesh Mini Skirt

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, high stretch
    • Large floral print on the front
    • Strapless straight-across neckline
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000513

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Flirty Mood Butterfly Print Mesh Halter Romper

    You didn’t just show up—you styled the entire night. This butterfly print mesh halter romper hugs in all the right places with a flirty, flowy fit made for parties, rooftop plans, and last-minute invites.

    Fit & Features

    • Mesh fabric with brushed knit lining, high stretch
    • Butterfly print
    • Sleeveless plunging cowl neckline, beaded bar strap accent
    • Halter tie-back straps, open back, dual lower back straps
    • Ruched drop waist
    • Flowy mini-length overlay, hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000258

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Keep It Spicy Fringe Halter Dress

    It’s the movement for me. This crochet halter dress brings texture, shape, and a fringe hem that does all the talking once you start strutting into festivals, parties, or vacations!

    Fit & Features

    • Crochet fabric, lined
    • V-neckline
    • Spaghetti straps
    • Cutout back detail
    • Bodycon fit
    • Fringe trim midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000327

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Effortlessly Polished Linen-Blend Cropped Vest

    Minimal effort, maximum polish—this one just gets it. This cropped linen-blend vest is lightweight, chic, and styles effortlessly from coffee runs to last-minute plans. Pair with the matching trouser pants.

    Shop Matching Bottoms: Effortlessly Polished Linen-Blend Trouser Pants

    Fit & Features

    • Linen-blend woven fabric, woven lining, no stretch
    • Sleeveless V-neckline
    • Tank shoulder straps
    • Button-down front
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06204-000132

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Effortlessly Polished Linen-Blend Trouser Pants

    Minimal effort, maximum polish—these just get it. These linen-blend trouser pants are lightweight, chic, and style effortlessly from coffee runs to last-minute plans. Pair with the matching cropped vest.

    Shop Matching Top: Effortlessly Polished Linen-Blend Cropped Vest

    Fit & Features

    • Linen-blend woven fabric, no stretch
    • High-rise waist, belt loops
    • Pleated detailing
    • Flowy wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000016

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Wild Instinct Zebra Floral Skirt

    Not your average statement maxi skirt—this one knows how to get attention without trying. The high-rise waist and ruching hug just right, with a side slit that flaunts your style from a chill dinner to dressed-up plans.

    Shop Matching Top: Wild Instinct Zebra Floral Top

    Fit & Features

    • Zebra rose print, mesh fabric with knit lining, high stretch
    • High-rise waist
    • Ruched seams
    • Side slit
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000141

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK/WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sunny Day Chic Thong Wedge Heels

    Booked, busy, and somewhere sunny. These thong wedge sandals give you an elevated style with a minimal strap design—perfect for getaways, brunch plans, and every outfit in between.

    Fit & Features

    • 3" Wedge heel
    • Almond toe
    • Thong-style strap
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-000042

    Category Name: Vacation Looks

    Price: $28.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Plans Tropical Tube Mini Dress

    Booked, busy, and already packing this. This floral print mini dress hugs you in all the right places and was made for beach stays, resort destinations, and tropical escapes!

    Fit & Features

    • Slinky knit-lined stretchy fabric
    • Tube strapless neckline
    • Statement floral print
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000571

    Category Name: Vacation Looks

    Price: $35.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Love This For Me Halter Mini Dress

    Soft, flirty, and already on your weekend lineup. This chiffon mini dress hugs your shape with a bodycon fit while the open back and ruffled trim keep things playful.

    Fit & Features

    • Chiffon fabric, smooth woven lining
    • Sweetheart halter neckline, padded bra cups, tie straps
    • Open back, stretchy smocked band
    • Ruffled trim
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000732

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: YELLOW, PINK

    Available Size: M, L

  • Playful Romance Floral Ruffle Mini Dress

    Romantic, but still a little playful. This floral mesh halter mini dress features a plunging neckline and tiered ruffle hem with a sash detail that moves effortlessly from brunch plans to sunset drinks.

    Fit & Features

    • Floral print, mesh-lined stretchy fabric
    • Plunge halter neckline with tie strap
    • Open back design with tie strap
    • A-line silhouette, ruffled trim detail
    • Side ruffled drape
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001337

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

  • Sweet Talker Floral Eyelet Midi Tube Dress

    Soft, fitted, and low-key stealing attention. This floral print eyelet midi tube dress hugs in all the right places with a stretchy feel that’s made for brunch plans, day dates, and everything after.

    Fit & Features

    • Eyelet knit fabric with sewn-in knit lining, high stretch
    • Floral print
    • Strapless elasticized straight-across neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000569

    Category Name: Vacation Looks

    Price: $35.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, L

  • Polished Escape Strappy Wedges

    Golden hour plans just found their perfect plus one. These strappy espadrille wedges give you that elevated feel without the effort, made for festivals, vacations, or weekend plans.

    Fit & Features

    • Wedge heel
    • Round toe
    • Strappy design with hoop
    • Closed ankle
    • Adjustable ankle strap with buckle closure
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000035

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Emmy Floral Cutout Formal Dress

    Special Occasion

    The Emmy dress is designed for moments when the room feels just a little brighter. Featuring a statement floral print and a sleek, floor-length mermaid silhouette, this strapless dress turns to reveal a striking cutout back with a hoop-strap insert for a modern, unforgettable finish.

    Fit & Features

    • Statement floral print, knit-lined fabric
    • Strapless neckline, non-slip grip lining
    • Hidden side zipper with hook-eye closure
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, cocktail soirees, summer galas, destination celebrations, honeymoons, vacations, anniversary dinners, milestone parties, graduations

    Style Number/Barcode: 05002-000878

    Category Name: Vacation Looks

    Price: $79.90

    Availability: In Stock

    Available Color: BLUE

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

    Product Badge:
    • Ships Free
  • Serving Chic Halter Cutout Bodycon Midi Dress

    Serving subtle drama with zero effort. This halter bodycon midi dress sculpts your shape with ribbed stretch and bold cutouts—made for nights when you want to feel chic and a little daring.

    Fit & Features

    • Hacci ribbed knit-lined fabric, high stretch
    • Sleeveless crew neckline
    • Halter tie-back straps, open back
    • Waist cutouts leading to an open lower back
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000666

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Spring Breeze Chiffon Maxi Dress

    Soft, floaty, and a little bit daring—this chiffon maxi dress features a high halter neckline, adjustable strappy open back, while the lace trim and flowy silhouette bring all the dreamy movement.

    Fit & Features

    • Airy chiffon fabric, woven lining
    • High halter neckline with tie straps
    • Side zipper and hook-eye closure
    • Adjustable strappy open back
    • Flowy maxi-length silhouette, lace trim throughout
    • Runs true to size

    Style Number/Barcode: 05101-001323

    Category Name: Vacation Looks

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free