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.

  • Back It Up Bodycon Mini Dress

    Last-minute invite? Say less—you’re already dressed. This halter mini dress hugs in all the right places with a textured finish and statement ring-back detail that hits from every angle.

    Fit & Features

    • Textured stretch fabric
    • Plunge halter neckline
    • Open back with hoop detail
    • Side slit accent
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000332

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

  • Palm Escape Halter Wide Leg Jumpsuit

    A tropical jumpsuit made for vacations, quick escapes, and weekend plans, soaking up the sun. The draped cowl neckline keeps it soft, the open back brings the drama, and the wide leg gives it that effortless flow.

    Fit & Features

    • Tropical print, knit stretchy fabric
    • Plunge cowl halter neckline
    • Open back
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000082

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Too Good To Skip Cutout Jumpsuit

    Yeah…this one’s getting noticed. This halter cutout jumpsuit snatches you in with a sleek fit and bold hoop details that hit from every angle—perfect for vacations, weekend plans, or nights out.

    Fit & Features

    • Slinky knit stretchy fabric
    • Halter neckline with tie straps
    • Cutout bodice with hoop inserts
    • Cutout back design
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000090

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: RUST-2

    Available Size: XS, S, M, L

  • Vacation Muse Floral Halter Maxi Dress

    This is the dress that makes every plan feel like a getaway. The plunging halter keeps it bold, while the floral appliqué brings that playful, standout detail.

    Fit & Features

    • Statement floral applique, stretch knit fabric
    • Plunge halter neckline
    • Open back design with tie
    • Center back slit
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000446

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Spotted And Booked Polka Dot A-Line Mini Dress

    Already RSVP’d and now you have the dress. This polka dot A-line mini dress hugs just right up top, then flares for that easy, flirty fit you’ll wear from dinner plans to after.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Polka dot print
    • Sleeveless V-neckline, eyelet trim, bow detail
    • Adjustable thin eyelet shoulder straps
    • Mini-length hem, ruffled trim
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000729

    Category Name: Vacation Looks

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Mindset Tropical Flower Heels

    These floral strap heels bring a soft, elevated feel with delicate straps and statement blooms perfect for vacations, bridal celebrations, or weekend looks.

    Fit & Features

    • 3.5" Stiletto heel
    • Square toe
    • Tropical flower inset
    • Strappy toe design
    • Luxe fit cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000633

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: WHITE

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

  • Always Out Animal Open Back Maxi Dress

    Walk in, and suddenly everyone’s paying attention. This cowl neck maxi dress drapes effortlessly with a bold print, open back, and high slit that was made for cocktail hour.

    Fit & Features

    • Animal print, mesh-lined stretchy fabric
    • Cowl halter neckline, tie straps
    • Open tie-back design
    • High side slit
    • Form-hugging maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000342

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

  • Marva Floral Lace-Up Mesh Formal Dress

    Special Occasion

    Sleek, sculpted, and made for a double-take moment—the Marva mesh mermaid gown is all about confident curves and effortless allure. Featuring a softly structured square neckline, delicate straps, and a lace-up back with ruched detailing, it’s designed to contour and captivate from every angle.

    Fit & Features

    • Floral abstract print, mesh fabric with full-length lining, moderate stretch
    • Sleeveless square neckline, spaghetti straps
    • Open strappy lace-up back design with tie closure
    • Ruched lower back detail
    • Floor-length mermaid silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, garden parties, formal outdoor events, anniversaries, vacations, honeymoons, baby showers, bridal showers, fancy brunches, and birthday dinners.

    Style Number/Barcode: 05002-001696

    Category Name: Vacation Looks

    Price: $64.90

    Availability: In Stock

    Available Color: BLUE

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

  • Fresh Bloom Floral Chiffon Mini Dress

    This floral mini dress features a strapless smocked bodice with layered ruffles that give you that flirty, floaty feel from day dates to weekend plans.

    Fit & Features

    • Floral print, chiffon fabric, lining
    • Strapless neckline
    • Stretchy smocked bodice
    • Layered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001036

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L

    Product Badge:
    • Sale
  • Pretty Vibe Eyelet Skater Dress

    Soft, flirty, and low-key unforgettable—this is the dress you reach for when the day turns into a whole moment. The eyelet skater dress hugs up top, flows out just right, and gives you that easy, pretty vibe from brunch to golden hour.

    Fit & Features

    • Woven eyelet fabric with lining
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Open tie-back design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000922

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XXS, XS, M, L

    Product Badge:
    • Best Seller
  • Serve Looks Mini Skort

    Cute, mini, and ready for whatever’s next. This bodycon skort gives you that sleek, snatched look with built-in shorts so you can move freely from day plans to night plans without overthinking it.

    Fit & Features

    • Woven fabric
    • Mid-rise waist
    • Bodycon fit
    • Mini-length hem
    • Built-in shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000166

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Polished But Fun Skater Mini Dress

    Clean, classic… and cuing all the compliments. This striped skater mini dress brings that tailored, put-together vibe with a cinched bodice and flared skirt perfect for sunny days.

    Fit & Features

    • Striped pattern, linen-like woven fabric
    • Square neckline, spaghetti straps
    • Hidden side pockets
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000776

    Category Name: Vacation Looks

    Price: $56.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Flirty Confidence Lace One-Shoulder Mini Dress

    A little bold, a little soft—exactly the balance you were going for. This lace one-shoulder A-line mini dress hugs up top and flares at the hem, giving you that confident, caught-in-the-moment kind of vibe.

    Fit & Features

    • Lace fabric with knit lining, high stretch
    • Sleeveless one-shoulder neckline, tank straps
    • Fitted bodice, ruched detailing
    • Drop waist design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000778

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

  • Golden Hour Crochet Halter Dress

    Booked for golden hour and not coming back early. This crochet halter mini dress features floral appliqué and a lace-up back that keeps things effortlessly pretty with just enough detail to stand out.

    Fit & Features

    • Crochet texture-lined knit fabric
    • Halter plunge neckline with beaded strap
    • Open back with lace-up design
    • Floral applique 
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000605

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S

  • Daydream Date Floral Maxi Dress

    This floral maxi dress flows with every step, featuring a square neckline and tiered ruffle layers that feel light, pretty, and ready for any invite and celebration!

    Fit & Features

    • Delicate floral print, chiffon-lined fabric
    • Square neckline, spaghetti straps
    • Tie-back design
    • Tiered ruffled A-line silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001029

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: WHITE

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

  • Dream State Flare Sleeve Crop Top

    A little sheer, a little mystical, exactly your vibe. This floral butterfly top features a plunge tie front neckline and bell sleeves that create a dramatically cute look for concerts, festivals, or nights-out.

    Shop The Matching Skirt: Dream State Ruffle Mini Skirt

    Fit & Features

    • Butterfly floral tie-dye print
    • Mesh-lined fabric
    • Long bell flare sleeves
    • Plunge tie-front neckline
    • Ultra-cropped length hem
    • Runs true to size 

    Style Number/Barcode: 06202-000108

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Sun Chasing Crochet Flower Bikini Bottom

    Serving major flirt energy. This crochet flower bikini bottom brings playful charm with delicate floral details and adjustable ties that make it perfect for festivals, vacations, and every sunny plan on your calendar.

    Shop Matching Top: Sun Chasing Crochet Flower Bikini Top

    Fit & Features

    • Crochet-lined fabric
    • Flower designs
    • Adjustable side ties 
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000030

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Sweet Touch Flower Earrings

    Instant outfit glow-up, no effort required. These resin flower drop earrings add a soft, feminine finish that makes even your simplest look feel styled.

    Fit & Features

    • Sculpted floral design
    • Attached hoop
    • Polished resin material 
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000351

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Nights Mesh Halter Maxi Dress

    Vacay booked. This tropical mesh maxi dress brings that breezy, curve-skimming fit with a trendy ruffled slit that moves with you from beach cocktails to dinner.

    Fit & Features

    • Tropical print, mesh fabric, soft knit lining
    • Halter V-neckline with hardware insert
    • Tie straps, open back
    • High front ruffled slit
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000607

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

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

  • Golden Hour Glow Metallic Crochet Mini Dress

    Golden hour glow mood. This metallic crochet one-shoulder mini dress hugs in all the right places and shows up ready for rooftop plans, dinners, and anything that turns into a photo moment.

    Fit & Features

    • Metallic crochet knit fabric, moderate stretch
    • Sleeveless one-shoulder neckline, tank strap
    • Metal flower hardware accents
    • Back zipper closure
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000451

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, L

  • Day Date Floral Print Puff Sleeve Midi Dress

    Effortless plans, elevated instantly. This floral print midi dress brings that easy, cinched-in fit with a pretty, flowy feel—perfect for brunch dates, garden parties, and everything in between.

    Fit & Features

    • Cotton-blend fabric with lining
    • Floral print
    • Square neckline, ruched bust
    • Short puff sleeves with cinched hems
    • V-shaped waist seam, stretchy smocked back
    • Midi-length flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001394

    Category Name: Vacation Looks

    Price: $64.90

    Availability: In Stock

    Available Color: WHITE, PRINT

    Available Size: S

  • Plans Booked Halter Slit Maxi Dress

    This is the dress you slip on when you want all eyes on you! Designed with a sleek halter neckline, curve-hugging fit, and statement front slit with hardware detail, this maxi dress brings the chic drama.

    Fit & Features

    • Knit stretchy fabric
    • Halter neckline, tie straps
    • Drop waist seam
    • High front slit
    • Curve-hugging fit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001180

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: XS, S, M, L

  • Heatwave Mood Bikini Bottoms

    Bring the heat in these bikini bottoms that sit high on the hips with side ties to adjust the fit and a cheeky bottom to flaunt your curves. Pair with the matching bikini top.

    Shop Matching Top: Heatwave Mood Bikini Top

    Fit & Features

    • Sleek knit fabric, high stretch
    • Low-rise waist
    • Adjustable side ties with beaded accents
    • Cheeky bottom
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000043

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: S, M, L

  • Heatwave Mood Bikini Top

    Bring the heat in this bikini top with flattering triangle cups and a trendy hardware insert for extra stylish flair. Pair with the matching bikini bottoms.

    Shop Matching Bottoms: Heatwave Mood Bikini Bottoms

    Fit & Features

    • Sleek knit fabric, high stretch
    • Triangle cups
    • Adjustable back ties
    • Hardware insert
    • Runs true to size

    Style Number/Barcode: 07104-000030

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: S, M, L