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.

  • Untamed Vibes Animal Print Halter Top

    A little daring, a lot confident—this top does not blend in. The draped halter neckline and curve-hugging fit make it a go-to for nights out, styled up with the matching skirt or worn solo when the vibe calls for extra.

    Shop Matching Skirt: Untamed Vibes Animal Print Maxi Skirt

    Fit & Features

    • Smooth knit fabrication
    • Sleeveless halter cowl neckline
    • O-ring accents
    • Lower back tie-back 
    • Leopard and snake print
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000469

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Untamed Vibes Animal Print Maxi Skirt

    She’s bold, she’s fierce, she moves like she owns the room. This curve-skimming maxi skirt brings drama with an effortless edge, perfect for nights out, styled solo or paired with the matching top.

    Shop Matching Top: Untamed Vibes Animal Print Halter Top

    Fit & Features

    • Smooth knit fabrication
    • Mid-rise waist
    • O-ring hardware accent at the waist
    • Leopard and snake print pattern
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000117

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Weekend Cool Mid-Rise Denim Jorts

    Casual but never boring—these are the jorts you throw on and somehow look styled. The relaxed mid-rise fit keeps things easy while still feeling intentional for brunch, errands, or off-duty hangs.

    Fit & Features

    • Structured denim fabrication
    • Mid-rise waist
    • Single button and hidden zipper closure
    • Relaxed jort silhouette
    • Knee-length hem
    • Five-pocket styling, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000146

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: S, M, L

  • Sweet Plans Eyelet Skater Dress

    Soft, flirty, and very much ready for plans. This eyelet skater dress brings that effortless charm with a flattering fit that feels easy, romantic, and wearable from day dates to sunset strolls.

    Fit & Features

    • Lightweight eyelet fabric with soft lining
    • Square neckline with adjustable bust tie detail
    • Sleeveless silhouette with wide straps
    • Fitted bodice with zip back closure
    • Flowy skater skirt with subtle tiered seam
    • Runs true to size

    Style Number/Barcode: 05101-000952

    Category Name: Vacation Looks

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Beauty Floral Halter Maxi Dress

    Bring the drama—this halter maxi dress mixes fierce animal print with bold florals for a look that’s equal parts wild and romantic. With its plunging neckline and curve-skimming fit, it’s ready for dinner downtown, rooftop hotel cocktails, or every moment you want to own.

    Fit & Features

    • Floral print design, mesh-lined stretchy fabric
    • Plunge halter neckline
    • Cutout bodice
    • Curve-hugging silhouette with high slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000685

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Made for the Moment Floral Maxi Dress

    Floaty, romantic, and made to move. This floral midi dress features cascading ruffles and a front slit that brings just enough drama while still feeling light, polished, and wearable for dressed-up plans.

    Fit & Features

    • Lightweight chiffon fabric with floral pattern
    • Slim-fit sweetheart bodice with spaghetti straps
    • Adjustable tie-back detail for customizable fit
    • Front slit with cascading ruffle trim
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000951

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Postcard Pretty Halter Cutout Maxi Dress

    Booked the dinner, ordered the spritz, now you need the dress. This halter maxi dress brings the drama with a rose detail, front cutout, and tiered skirt that moves like you planned this all along.

    Fit & Features

    • Lightweight woven fabric with abstract print
    • Halter neckline with rosette detail
    • Front cutout with twist front bodice
    • Smocked back for stretch
    • Tiered ruffled maxi skirt
    • Runs true to size

    Style Number/Barcode: 05102-000411

    Category Name: Vacation Looks

    Price: $62.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Sun Chasing Ribbed Knit Halter Midi Dress

    Hot plans? Found the dress. This ribbed knit halter bodycon midi dress hugs in all the right places with a ruched bust and flirty keyhole cutout—aka your go-to for birthday dinners, rooftop nights, and every RSVP in between.

    Fit & Features

    • Ribbed sweater knit fabric, high stretch
    • Sleeveless sweetheart neckline
    • Tie-back halter spaghetti straps
    • Ruched bust, keyhole cutout
    • Midi-length hem, high-cut side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000286

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BANANA

    Available Size: S, M, L

  • Undeniable Allure Halter Cutout Mini Dress

    She doesn’t enter quietly—she arrives undeniable. A plunging halter cutout mini dress with bold metal hardware and a body-hugging fit that was made for rooftop nights, vacation dinners, and any plan that deserves extra.

    Fit & Features

    • Textured knit fabric, high stretch
    • Sleeveless plunging V-neckline
    • Dual circular metal hardware accents, waist cutouts
    • Tie-back halter straps
    • Open back, lower tie-back spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000417

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Coastal Crush Beaded Thong Sandals

    POV you’re five minutes from the beach, and your outfit is already winning. These beaded thong sandals keep it easy with a flat sole and shell inspired details that instantly elevate your warm-weather lineup.

    Fit & Features

    • Smooth faux leather upper
    • Thong sandal silhouette
    • Beaded strap with shell-inspired accents
    • Flat sole with slip-on design
    • Runs true to size

    Style Number/Barcode: 07404-000065

    Category Name: Vacation Looks

    Price: $20.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachside Bold Abstract Print High-Cut Bikini Bottoms

    Sun on your skin, confidence on repeat. These abstract print bikini bottoms bring a cool edge that feels styled and trendy—perfect for beach days that turn into golden-hour plans. Pair with the matching bikini top.

    Shop Matching Top: Beachside Bold Abstract Print Beaded Bikini Top

    Fit & Features

    • Smooth stretch knit fabric, abstract print
    • High-cut design
    • Ultra-cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000025

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

  • Layered Luxe Bracelet Five-Pack

    Stacked and styled in seconds. This five-pack bangle bracelet mixes sleek metal bands with a bold hinge bangle for that effortless layered look, no overthinking required.

    Fit & Features

    • Five-pack bangle bracelet set
    • Various styles and designs
    • Hinge closure and slip-on styles

    Style Number/Barcode: 07003-000196

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Petals On Repeat Floral Earrings

    Soft glam, but make it playful. These floral drop earrings bring a flirty, feminine touch with cascading blooms that instantly dress up your brunch fits and date-night looks.

    Fit & Features

    • Linear drop silhouette
    • Triple floral design
    • Textured center detail
    • Post back closure

     

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

    Style Number/Barcode: 07001-000272

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Angles Textured Hoop Earrings

    Minimal effort, maximum polish. These textured hoop earrings add just enough shine and detail to make your everyday fit feel styled in seconds.

    Fit & Features

    • Polished construction
    • Medium hoop silhouette
    • Textured etched front detail
    • Post back closure

     

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

    Style Number/Barcode: 07001-000332

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Breezy Off-Shoulder Poncho Top

    That effortless throw-on and go layer. This crop poncho top drapes off the shoulder with a relaxed fit that pairs perfectly with denim, boots, and stacked jewelry for an easy, cute vibe.

    Fit & Features

    • Texture knit fabric
    • Off-shoulder neckline
    • Relaxed cropped silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000311

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN, IVORY, WINE

    Available Size: XS/S, M/L

    Product Badge:
    • Back In Stock
  • Butterfly Effect Chain Halter Top

    Serving art piece energy with a flirty twist, this abstract halter brings the drama with a plunging neckline and butterfly chain detail create a statement moment, while the open back keeps it effortlessly bold. 

    Fit & Features

    • Abstract print, knit, stretchy fabric
    • Plunge halter neckline with butterfly swag chain
    • Open back with dual straps
    • Open front design
    • Crop-length silhouette
    • Runs true to size

    Style Number/Barcode: 06001-000317

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Island After Hours One Shoulder Maxi Dress

    This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.

    Fit & Features

    • Tropical floral print knit fabric
    • One-shoulder neckline
    • Statement hardware strap detail
    • Front slit with ruffle accent
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-000419

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

  • Modern Fairytale Lace Ruffle Mini Dress

    Perfect for bridal events, birthday dinners, or any moment that deserves a little extra glow, this mini dress brings soft romance. Just add delicate heels and jewelry for a look that feels effortless but completely put together.

    Fit & Features

    • Lace-lined fabric
    • Strapless neckline
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000508

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: WHITE, SAGE

    Available Size: L, XS, S, M

  • Wildly Fierce Leopard Floral Maxi Dress

    Warning: this dress doesn’t do low profile. The leopard floral mesh print fabric and plunge halter neckline with bead inset sculpt a form-hugging maxi silhouette that’s made for vacations, birthday dinners, and any plan that deserves a little drama.

    Fit & Features

    • Floral, leopard print mesh-lined fabric
    • Plunge halter neckline with tie and bead
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000365

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Such A Flirt Polka Dot Mesh Mini Skort

    Okay, but this skort just RSVP’d yes for you. This polka dot mesh mini skort drapes perfectly with a tiered ruffled design and flirty A-line fit, making it your go-to for party plans, birthday dinners, or that last-minute invite that has you walking in like you planned it all week.

    Shop Matching Top: Such A Flirt Polka Dot Mesh Cowl Neck Top

    Fit & Features

    • Polka dot mesh fabric, high stretch
    • Mid-rise waist with ruching
    • Tiered ruffled design
    • Mini-length overlay, A-line silhouette
    • Hidden fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000245

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK/WHITE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Kim Rhinestone Leopard Mermaid Formal Dress

    Special Occasion

    Designed to command attention the moment you arrive, the Kim rhinestone leopard gown brings bold glamour to any formal setting. The mermaid floor-length silhouette is finished with a striking cutout back that feels confident, sculpted, and unforgettable.

    Fit & Features

    • Rhinestone embellished mesh-lined fabric, leopard pattern
    • Plunge V-neckline, wide shoulder straps
    • Side zipper and hook-eye closure
    • Cutout back detail
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, black-tie galas, weddings, red-carpet occasions, formal birthday celebrations, upscale receptions, fancy art gallery openings, award show dinners, special date nights

    Style Number/Barcode: 05002-001039

    Category Name: Vacation Looks

    Price: $159.90

    Availability: In Stock

    Available Color: BLACK, PRINT

    Available Size: M, L

    Product Badge:
    • Ships Free
  • Bare Minimum Drama Sequin Crochet Fringe Poncho

    Sheer, shimmery, and not here to blend in. This sequin crochet fringe poncho is the ultimate layer when your bikini top or bralette deserves a little extra attention, but you still want that effortless, thrown on and thriving vibe.

    Fit & Features

    • Lightweight sheer crochet fabric
    • Sequin embellishments
    • Relaxed poncho silhouette
    • Open neckline with easy slip-on design
    • Fringe hem
    • Runs true to size

    Style Number/Barcode: 06005-000288

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S

  • Chic Vibes Only Flyaway Top

    Hot take, this is not your basic layer. This mesh halter open flyaway top floats behind you with every step, giving beach party, festival night, or content shoot energy without even trying.

    Fit & Features

    • Sheer mesh fabrication
    • Longline open tunic silhouette
    • Halter neckline with cross strap detail
    • Relaxed draped fit
    • Runs true to size

    Style Number/Barcode: 06001-000455

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Dripping In Drama Hammered Lariat Necklace

    Serving poolside goddess with zero effort. This hammered lariat necklace drops low with bold statement shine, instantly elevating plunging necklines, swim looks, or that pic-worthy dress you’ve been saving.

    Fit & Features

    • Metal construction with hammered texture
    • Long lariat silhouette
    • Oversized shaped pendants

    Style Number/Barcode: 07002-000371

    Category Name: Vacation Looks

    Price: $19.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free