Vacation Looks

Loading...

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.

  • Soft Focus Muse Floral Lace-Up Maxi Tube Dress

    Caught feelings for this one instantly. This floral maxi tube dress hugs just right with a lace-up back that brings a little extra drama for nights out or dressed-up day plans.

    Fit & Features

    • Smooth stretch knit fabrication
    • Sleeveless ruched sweetheart neckline
    • Large floral pattern
    • Lace-up back design
    • Maxi-length hem 
    • Runs true to size

    Style Number/Barcode: 05101-001120

    Category Name: Vacation Looks

    Price: $14.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spritz And Plans Strapless Mini Dress

    This dress has "take me on vacay" written all over it! The playful print and easy strapless fit keep it light, while the flowy mini hem makes it perfect for enjoying a sunny day on your next getaway.

    Fit & Features

    • Garden fruit and veggie print, woven fabric, stretchy knit lining
    • Strapless neckline, stretchy smocked bodice
    • Fit and flare silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000615

    Category Name: Vacation Looks

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Maia Floral Print Sequin Mermaid Dress

    Special Occasion

    Cue the compliments in the Maia sequin mermaid dress that shimmers with a dreamy floral print that feels straight out of a getaway moment. The sculpted silhouette hugs in all the right places, while delicate straps and an open lace-up back keep it effortlessly alluring.

    Fit & Features

    • Knit fabric with large floral print, full-length knit lining, moderate stretch
    • All-over clear sequin embroidery
    • Sleeveless V-neckline, padded bust
    • Spaghetti straps
    • Open lace-up strappy back with tie closure, lower back zipper with hook-eye closure
    • Floor-length mermaid silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, birthday celebrations, vacations, honeymoons, resorts, and summer parties.

    Style Number/Barcode: 05002-000614

    Category Name: Vacation Looks

    Price: $19.97 $119.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunlit Muse Paillette Sequin Mini Cover-Up

    Shimmer that catches the light and refuses to be subtle. This paillette sequin bikini cover-up features a side tie closure that keeps the fit adjustable for beach days, poolside lounging, or sunset photos. Style with the matching bikini top and bottoms.

    Shop Matching Set: Sunlit Muse Paillette Sequin Bikini Top, Sunlit Muse Paillette Sequin Bikini Bottoms

    Fit & Features

    • Mesh fabric, smooth sewn-in knit lining, moderate stretch
    • Paillette sequin embroidery
    • Side tie closure
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07105-000037

    Category Name: Vacation Looks

    Price: $12.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkly Rhinestone Thong Sandals

    A little sparkle goes a long way—these metallic rhinestone thong sandals bring just enough shine to dress up your look.

    Fit & Features

    • Almond toe
    • Rhinestone-embellished thong strap
    • Flat sole
    • Metallic material
    • Traction bottom

    Style Number/Barcode: 07404-000045

    Category Name: Vacation Looks

    Price: $16.90

    Availability: In Stock

    Available Color: GOLD

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

  • 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: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: In Stock

    Available Color: IVORY

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

  • 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: $9.97 $42.90

    On Sale: Yes

    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: $14.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • 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: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $14.97 $32.90

    On Sale: Yes

    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: 05102-000734

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: PINK, WHITE

    Available Size: L, S, M

  • 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: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $19.97 $79.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • 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: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Finish Strappy Sandals

    These strappy sandals keep it minimal with a sleek silhouette and a hint of hardware that pulls your whole look together. Perfect for everyday styling, vacations, or weekend looks.

    Fit & Features

    • Square toe
    • Strappy design with hardware detail
    • Flat sole, luxe fit cushioned insole
    • Faux leather material
    • Slip-on style
    • Runs true to size

    Style Number/Barcode: 07404-000068

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Heat Mesh Maxi Dress

    Booked, busy, and dressed like it. This tropical floral maxi dress is form-hugging with a high side slit that brings just enough drama for your next getaway or sunset dinner.

    Fit & Features

    • Tropical floral print, mesh fabric, brushed knit lining
    • Strapless tube neckline, non-slip grip lining
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000626

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibe Butterfly Print Mesh Halter Top

    A little flirty, a little hard to ignore—exactly your vibe. This butterfly print mesh halter top drapes with a soft cowl neckline and features O-ring accents and an open back for a fab vibe. Style with the matching maxi skirt.

    Shop Matching Bottoms: Flirty Vibe Butterfly Print Mesh Maxi Skirt

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, high stretch
    • Butterfly print
    • Sleeveless plunging cowl neckline
    • Halter tie-back spaghetti straps, metal O-ring hardware accents
    • Open back, lower tie-back straps
    • Mid-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000512

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS

    Product Badge:
    • Sale
  • Sunset Muse Ombre Mesh Cutout Maxi Dress

    Serving curves, movement, and just enough drama. This ombre mesh cutout maxi dress hugs in all the right places with a fluid drape that feels effortless but looks unforgettable.

    Fit & Features

    • Ombre sheer mesh fabric with full-length knit lining, high stretch
    • Sleeveless plunging cowl neckline, bar strap detail
    • Halter tie-back straps
    • Asymmetric waist cutouts leading to an open back
    • Maxi-length hem, floor-length center sash accent
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001168

    Category Name: Vacation Looks

    Price: $14.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Luxe Nights Halter Mini Dress

    This is the dress you wear when subtle isn’t the plan. This halter mini dress sculpts with a ruched designa plunging neckline, and statement hardware that pulls it all together—perfect for nights out or that last-minute RSVP.

    Fit & Features

    • Smooth knit fabric with moderate stretch
    • Plunge halter neckline, hardware inset
    • Open back design
    • Ruched bodycon mini silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000711

    Category Name: Vacation Looks

    Price: $20.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free