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.

  • Floating Moment Pleated Palazzo Pants

    Float through the day in these effortless pleated palazzo pants. The lightweight chiffon fabric creates soft movement with every step, while the relaxed silhouette keeps your look easy and polished. Perfect for dressing up with heels or keeping it breezy with sandals.

    Fit & Features

    • Chiffon-lined fabric
    • High-rise waist
    • Flowy wide-leg silhouette
    • Pleated design
    • Runs true to size

    Style Number/Barcode: 06402-000031

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Sunkissed Edge Snake Print Triangle Bikini Top

    A little wild, a lot confident. This snake print triangle bikini top features a sleek, minimal look with adjustable straps and a tie-back design that lets you customize the fit your way. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Sunkissed Edge Snake Print Bikini Bottoms

    Fit & Features

    • Smooth stretch knit fabric
    • Snake print
    • Triangle design
    • Adjustable spaghetti straps
    • Open back, tie-back spaghetti straps
    • Runs true to size

    Style Number/Barcode: 07104-000023

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: SNAKE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Sunkissed Edge Snake Print Bikini Bottoms

    A little wild, a lot confident. These snake print bikini bottoms feature a sleek, minimal look with adjustable side ties that let you customize the fit your way. Style with the matching bikini top.

    Shop Matching Top: Sunkissed Edge Snake Print Triangle Bikini Top

    Fit & Features

    • Smooth stretch knit fabric
    • Snake print
    • Side tie closures
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000032

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: SNAKE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Weekend Style Studded Slide Sandals

    These slide sandals add just the right amount of edge with a studded design for an effortless look.

    Fit & Features

    • Square toe
    • H-shaped band with studs
    • Flat sole
    • Cushioned insole
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07404-000046

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: TAUPE

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

  • Tropical Tresses Hair Claw Clip Set

    Brighten your tresses with this three-pack hair claw clip set! Designed in blooming tropical florals with claw clip closures for a secure grip, these hair clips are perfect for vacations!

    Fit & Features

    • Three-pack hair claw clip set
    • Tropical floral design
    • Claw closure

    Style Number/Barcode: 07006-000136

    Category Name: Vacation Looks

    Price: $11.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Coast Hoop Detail Bikini Bottoms

    These bikini bottoms are serving effortless allure with attitude. The classic bikini bottoms get an upgrade with hoop insets and a sleek back ruched seam that highlights your shape from every angle. Shop the matching bikini bottom.

    Shop Matching Top: Golden Coast Hoop Detail Bikini Top

    Fit & Features

    • Sleek knit fabric
    • Mid-rise fit
    • Hoop side inserts
    • Back ruched seam
    • Cheeky bottom
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000034

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BROWN, MINT

    Available Size: S, M, L

  • Golden Coast Hoop Detail Bikini Top

    This bikini top is serving effortless allure with attitude. The classic triangle silhouette gets an upgrade with hoop insets and sleek wraparound straps that highlight your shape from every angle. Shop the matching bikini bottom.

    Shop Matching Bottoms: Golden Coast Hoop Detail Bikini Bottoms

    Fit & Features

    • Sleek knit fabric
    • Triangle bust with hoop insert
    • Wrap-around tie detail
    • Adjustable spaghetti straps
    • Tie-back detail
    • Runs true to size

    Style Number/Barcode: 07104-000037

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: MINT, BROWN

    Available Size: S, M, L

  • Goes With Everything Thong Sandals

    Simple, sleek, and always in rotation. These thong sandals keep it minimal with a clean silhouette that goes with everything, making them your easy grab for errands, weekend plans, and last-minute outfit saves!

    Fit & Features

    • Square toe design
    • Minimal thong toe strap
    • Cushioned footbed
    • Flat sole
    • Luxe fit cushioned sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000047

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shimmer Steps Rhinestone Slide Sandals

    A little sparkle goes a long way. These rhinestone strap slide sandals add an easy glow to everyday outfits with a cushioned sole and effortless slip-on fit that works for parties, brunch, or vacation strolls.

    Fit & Features

    • Square toe
    • Multiple rhinestone criss-cross strap design
    • Flat sole
    • Cushioned footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000001

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: SILVER

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

  • Chic Steps Braided Block Heels

    The heels that instantly elevate every outfit. These block heels feature braided straps and a sleek block heel for a polished look that’s chic for brunch, showers, and dressy occasions.

    Fit & Features

    • Block heel
    • Square toe
    • Braided straps
    • Adjustable ankle strap with buckle closure
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000333

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

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

  • Pretty Petals Flower Hair Claw Clip Set

    Cute hair day incoming. This flower hair claw clip set makes styling feel effortless with playful petal designs that add a soft, fun finish to any look.

    Fit & Features

    • Three-pack hair claw clip set
    • Varying-sized flower designs

    Style Number/Barcode: 07006-000138

    Category Name: Vacation Looks

    Price: $11.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Styled And Booked Halter Top

    This top is what you throw on when the plan is “look cute, no stress.” This paisley halter top drapes effortlessly with a tie front and flowy fit—perfect with denim when you want that styled but chill vibe.

    Fit & Features

    • Paisley print, woven fabric
    • Halter neckline with tie front
    • Open back with stretchy smocked panel
    • Flowy flyaway crop silhouette
    • Runs true to size

    Style Number/Barcode: 06003-000278

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sunkissed Siren Beaded Abstract Print Bikini Bottoms

    Soft glow, sun-kissed skin, and these bikini bottoms doing all the talking. The abstract print and beaded details give you that effortlessly styled look that feels just as good lounging poolside as it does layered under denim. Style with the matching bikini top.

    Shop Matching Top: Sunkissed Siren Beaded Abstract Print Bikini Top

    Fit & Features

    • Knit fabric, high stretch
    • Abstract print
    • Beaded accents
    • Tie-side closures
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000026

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Sunkissed Siren Beaded Abstract Print Bikini Top

    Soft glow, sun-kissed skin, and this bikini top doing all the talking. The abstract print and beaded details give you that effortlessly styled look that feels just as good lounging poolside as it does layered under denim. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Sunkissed Siren Beaded Abstract Print Bikini Bottoms

    Fit & Features

    • Knit fabric, high stretch
    • Abstract print
    • Triangle design, center turquoise-embellished oval-shaped accent
    • Halter tie-back spaghetti straps, beaded accents
    • Lower tie-back spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07104-000018

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

  • Double Take Floral Chiffon Ruffle Maxi Dress

    Cue the double takes. This floral chiffon maxi dress brings the drama with ruffles, cutouts, a flirty slit, and breezy movement that shows up beautifully everywhere from brunch plans to sunset parties.

    Fit & Features

    • Sheer chiffon fabric with full-length stretchy knit lining
    • Sleeveless sweetheart neckline, no-slip strip, padded bust, knotted center
    • Halter tie-back straps, stretchy smocked back
    • Asymmetric side cutouts leading to an open lower back
    • Ruffled design, high-cut front slit
    • Maxi-length flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000888

    Category Name: Vacation Looks

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Minimal Muse Bodycon Midi Dress

    Your new go-to dress when the vibe is effortlessly polished. This bodycon midi dress hugs in all the right places while the side slit offers effortless allure for brunch plans, vacations, or sunset cocktails.

    Fit & Features

    • Sweater knit fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Side slit
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000349

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: TAUPE, ORANGE, MAGENTA

    Available Size: S, M, L

  • Bold Allure Abstract Animal Print Mini Skort

    Not here to blend in—this one sets the tone. This abstract animal print mini skort hugs just right with a mid-rise waist, tiered ruffled design, and airy mesh feel that keeps things bold but effortless. Style with the matching halter top.

    Shop Matching Top: Bold Allure Abstract Animal Print Halter Top

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract animal print
    • Mid-rise waist
    • Tiered ruffled design, mini-length overlay, A-line fit
    • Tie detail, short side slit
    • Hidden fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000237

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: S, L

    Product Badge:
    • Part of a Set
  • City Walk Tortoise Oversized Sunglasses

    Put these on, and suddenly your outfit feels more put-together. These oversized tortoise sunglasses bring that effortless polish with a bold frame that works from coffee runs to weekend plans.

    Fit & Features

    • Tinted lenses
    • Oversized sunglasses silhouette
    • Square shape with rounded edges
    • Tortoise pattern

    Style Number/Barcode: 07008-000168

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love The Drama Oversized Sunglasses

    A little mysterious, a little extra—in the best way. These oversized sunglasses give instant polish with a bold shape that pulls your whole look together, even on your most off-duty days.

    Fit & Features

    • Tinted lenses
    • Oversized sunglasses silhouette
    • Rounded square shape

    Style Number/Barcode: 07008-000174

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • It Girl Energy Rimless Shield Sunglasses

    These are giving instant main character. The rimless shield design with that warm tinted lens hits different—sleek, bold, and a little futuristic. Perfect for when your outfit needs that extra edge without trying too hard.

    Fit & Features

    • Rimless shield sunglasses design
    • Tinted lenses with warm tone finish
    • Rubber nose supports
    • Lightweight metal frame construction

    Style Number/Barcode: 07008-000178

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Little Plans Eyelet Ruffle Romper

    Cute plans call for something this good. This eyelet romper features delicate straps, a softly ruched bodice, and a flirty tiered skirt that gives you the look of a mini dress with the comfort of built-in shorts.

    Fit & Features

    • Eyelet fabric
    • V-neckline with adjustable spaghetti straps
    • Ruched fitted bodice
    • Tiered flowy skirt with built-in shorts
    • Runs true to size

    Style Number/Barcode: 06503-000248

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Sweet Babe Floral Skater Mini Dress

    This dress feels like a soft summer day. The airy chiffon, delicate floral print, and flirty tiered skirt give it that effortless romantic vibe. Finished with a lace-up back for a little extra charm at parties, brunch, or any dressy occasion.

    Fit & Features

    • Floral print chiffon-lined fabric
    • Sweetheart neckline, twist bust
    • Spaghetti straps that shape the lace-up back
    • Skater silhouette
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000866

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: YELLOW

    Available Size: L

    Product Badge:
    • Sale
  • Ocean Daydream Seashell Mini Dress

    Catch flights or just compliments in this mini dres that hugs just right with delicate shell details and a breezy open back made for sunny getaways and golden hour dinners.

    Fit & Features

    • Crochet knit-lined fabric with seashell embellishments
    • V-neckline
    • Spaghetti straps shape the lace-up back design
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000536

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Paradise Ready Floral Maxi Dress

    Unlock vacation energy in this floral maxi dress perfect for cocktail dinners, sunset strolls, and looking chic on the beach! This dress is designed in a flattering mermaid fit with a flared hem that brings effortless drama to every step.

    Fit & Features

    • Statement tropical floral print
    • Mesh fabric lined with soft knit
    • Tube strapless neckline
    • Mermaid fit
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001141

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: NATURAL

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