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.

  • Flowy Mood Chiffon Ruffle Poncho

    Light, airy, and a little bit extra in the best way. This flowy chiffon ruffle poncho drapes effortlessly with an off-the-shoulder moment that feels both relaxed and styled for wherever the day takes you.

    Fit & Features

    • Chiffon fabric with lining
    • Asymmetric off-the-shoulder neckline
    • Ruffled sleeves
    • Cropped hem
    • Flowy fit
    • Runs true to size

    Style Number/Barcode: 06003-000408

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: IVORY, MINT

    Available Size: S, M, L

  • Meet Me Out Beaded Handle Bag

    Booked the reservation just to carry this. This raffia bag features a statement beaded handle and spacious interior—perfect for brunch, strolling beach cities, and every outfit that needs a little extra.

    Fit & Features

    • Beaded straps
    • Detachable crossbody strap
    • String tie accents
    • Slouchy silhouette
    • Spacious interior
    • Raffia material

    Style Number/Barcode: 07203-000144

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

    Product Badge:
    • Best Seller
  • Heat Check Halter Crop Top

    Outfit planned before the invite even drops. This abstract print crop top drapes just right for nights out, last minute plans, and everything after.

    Fit & Features

    • Abstract print, sheer mesh fabric
    • Cowl halter neckline with tie straps
    • Open back with tie strap
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000703

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: M, L

  • Play Nice Twist Strap Crop Top

    Cute with a little attitude, just how you like it. This abstract floral tank top features trendy twist shoulder straps and a fitted crop hem that hugs in all the right places and levels up your everyday fits.

    Fit & Features

    • Abstract floral print, mesh-lined fabric
    • Square neckline
    • Twist shoulder straps
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000710

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: S, M, L

  • Prowlin' Tiger Mesh Mini Dress

    Spotted: you owning every room you walk into. This tiger print mesh mini dress features a strapless neckline and breezy A-line fit—perfect for downtown plans, birthday dinners, and when your outfit needs to do the flirting.

    Fit & Features

    • Tiger print, sheer mesh fabric, lined
    • Strapless neckline
    • Flowy A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000962

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

  • Retro Crush Floral Chiffon Mini Dress

    Serving vintage flirt energy in this floral mini dress. It brings the vibe with a breezy A-line fit, playful cutouts, and a tie-front bust made for sunny days.

    Fit & Features

    • Vintage-inspired floral print
    • Chiffon fabric, smooth woven lining
    • V-neckline, tie-front bust, adjustable spaghetti straps
    • Stretchy smocked back panel
    • Side cutouts along the bodice
    • A-line fit, ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000775

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: LAVENDER

    Available Size: S, M, L

  • Go With Everything Jelly Thong Sandals

    No effort, still looks put together. These clear jelly thong sandals are your easy grab for beach days, errands, and everything in between.

    Fit & Features

    • Curved, round toe design
    • Thong toe strap
    • Flat sole
    • Clear jelly material

    Style Number/Barcode: 07404-000071

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: CLEAR

    Available Size: 5, 6, 7

  • Vacay Calling Wide Leg Jumpsuit

    Booked the vibe before the trip even started. This tropical print jumpsuit flows easily with every step, perfect for sunset dinners, strolling the beach, or wherever the day takes you.

    Fit & Features

    • Tropical floral leaf print, knit fabric, bust lining
    • Tube strapless neckline
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000089

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

  • Laren Metallic Halter Mermaid Formal Dress

    Special Occasion

    Designed to captivate from every angle, the Laren metallic knit mermaid gown brings sleek drama to the moment. A plunge halter neckline with hardware draws the eye, while an open bar back and fluid floor-length hem create a striking, sculpted finish.

    Fit & Features

    • Metallic knit-lined fabric with plenty of stretch
    • Plunge halter neckline with statement hardware detail
    • Cutout waist design, back zipper and hook-eye closure
    • Open bar back for an elevated, modern reveal
    • Mermaid floor-length silhouette
    • Runs true to size 

     

    Where to Wear:

    Destination weddings, vacations, getaways, luxury resort celebrations, anniversary dinners, fashion-forward occasions, cocktail parties

    Style Number/Barcode: 05002-000993

    Category Name: Vacation Looks

    Price: $79.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Sunlit Flirt Floral Lace Ruffle Skater Dress

    This one just made your weekend plans a little cuter. Designed in floral lace with a flirty ruffle skater silhouette, this mini dress hugs up top and flares out for that effortless, twirl-worthy finish.

    Fit & Features

    • Sheer floral lace fabric with knit lining, moderate stretch
    • Strapless sweetheart neckline, knot-front bust
    • V-shaped drop waist seam
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001024

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: YELLOW

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

  • Simply Sweet Ruffle Skater Dress

    Consider this your excuse to romanticize even the simplest plans. The ruffle skater dress hugs up top with a soft stretch fit, then flows into that twirl-ready skirt made for brunch dates, parties, and everything in between.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless V-neckline, ruched bust
    • Adjustable spaghetti straps
    • V-shaped drop waist seam
    • Asymmetric tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001227

    Category Name: Vacation Looks

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Cute Bodycon Mini Dress

    This one just feels like a good idea. A ruched tank mini dress that smooths and shapes with a barely-there feel, made for last-minute plans you’re definitely saying yes to.

    Fit & Features

    • Smooth knit-lined stretch fabrication
    • V-neckline with tank straps
    • All-over ruched detailing
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000704

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Chic Agenda Plunge Maxi Dress

    From meetings to martinis without missing a beat. This cap sleeve maxi dress with a center drape accent and front slit keeps it polished for work hours and chic for after-hours plans.

    Fit & Features

    • Smooth knit stretch fabric
    • Cao sleeves with shoulder pads for structure
    • Plunge V-neckline
    • Center front drape and slit designs
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000784

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M, L

  • RSVP Pretty Floral Chiffon Maxi Dress

    If the invite says dress up, this floral chiffon dress is ready to make an entrance. Designed to flow effortlessly with a cinched waist and airy skirt that feels just right for showers, brunches, and every dressy celebration. 

    Fit & Features

    • Floral pattern, chiffon fabric, smooth woven lining
    • Halter neckline with tie straps
    • Ruched bodice detail
    • Back zipper and hook-eye closure
    • Flowy A-line silhouette
    • Handkerchief maxi hem
    • Runs true to size

    Style Number/Barcode: 05101-001393

    Category Name: Vacation Looks

    Price: $64.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, L

  • Hot Plans Halter Crop Top

    Cute plans just found their top. This textured halter crop top ties at the neck with a sculpted fit that keeps things sleek and ready for sunny days, festivals, and vacations.

    Fit & Features

    • Textured fabric
    • Halter neckline with tie straps
    • Open back
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-000337

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: XS, S, M, L

  • Golden Hour Charms Double Layer Belly Chain

    Tiny details, big impact. This double-layered belly chain stacks delicate charms for that effortless styled vibe, whether it’s peeking over denim or paired with your beach plans.

    Fit & Features

    • Layered metal belly chain
    • Mixed charms with cross and gem accents
    • Layered stacked silhouette
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07002-000390

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Hot Plans Tie Front Ruffle Sleeve Top

    This one’s already booked for your next night out. This tie front ruffle sleeve top gives you that easy flirty fit with an adjustable front and a little movement in the sleeves for extra charm. Pair with the matching skirt for a look that turns heads.

    Shop Matching Bottoms: Hot Plans High Waist Ruffle Midi Skirt

    Fit & Features

    • Soft stretch knit fabrication
    • V-neckline with tie-front closure
    • Short ruffled sleeves
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000112

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: NEON, PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Vacation Glow Beaded Stiletto Heel Sandals

    Serving sunset plans and cute outfit pics only. These beaded stiletto heel sandals bring all the playful detail with a barely-there fit that instantly elevates your going-out looks.

    Fit & Features

    • Faux leather material
    • Strappy silhouette
    • Adjustable ankle strap
    • Beaded front strap detail
    • Stiletto heel
    • Runs true to size

    Style Number/Barcode: 07401-000642

    Category Name: Vacation Looks

    Price: $32.90

    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
  • She's Bold Abstract Floral Midi Tube Dress

    She’s bold, effortless, and fully booked. This abstract floral print midi tube dress hugs your curves with a smooth stretch fit—perfect for when you want your outfit to do all the talking.

    Fit & Features

    • Sleek knit fabric, high stretch
    • Abstract floral print
    • Strapless straight-across neckline
    • Ruched detailing
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000585

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: ORANGE

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

  • Pretty Little Crepe Skater Dress

    Polished, but still feels effortless. This crepe skater dress brings a refined shape with a square neckline and lace-up back—perfect for brunches, showers, or any invite that calls for something a little elevated.

    Fit & Features

    • Crepe woven fabric, smooth woven and tulle linings
    • Square neckline, lightly padded bra cups
    • Adjustable shoulder straps
    • Lace-up back, zipper and hook-eye closure
    • Drop waist seam
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000889

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: PINK

    Available Size: M, L

  • Wild Attraction Cowl Neck Maxi Dress

    Serving curves with a side of attitude. This leopard print mesh cowl neck maxi dress drapes just right with an open back and hardware detail that makes every step feel a little extra.

    Fit & Features

    • Leopard print, mesh fabric, knit lining
    • Plunge cowl neck halter neckline, hardware insert
    • Open back
    • Curve-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000393

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: PINK

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

  • Make It A Moment Halter Romper

    Serving just enough drama without overthinking it. This knit plunge halter romper shows off with an open back and tiered ruffles that move with you for any plans.

    Fit & Features

    • Stretchy knit fabric
    • Plunge halter encklien with tie straps
    • Open back
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06503-000267

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: XS, S, M, L

  • In My Lace Era Mini Skort

    Serving legs with a little extra detail—because basics just aren’t cutting it. This lace-trim mini skort hugs your shape while keeping things effortless from brunch plans to last-minute invites.

    Fit & Features

    • Ponte knit fabric with moderate stretch, sheer lace trim
    • High-rise waist
    • Mini-length overlay, form-hugging fit
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000300

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Hot Plans High Waist Ruffle Midi Skirt

    This one’s already booked for your next night out. This high-waisted ruffled skirt gives you an easy, flirty look with a flattering fit and feel throughout for extra charm. Pair with the matching tie-front top for a look that turns heads.

    Shop Matching Top: Hot Plans Tie Front Ruffle Sleeve Top

    Fit & Features

    • Soft stretch knit fabrication
    • High-rise waist with ruffle accent
    • High side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000158

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NEON, PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set