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.

  • Chic Mood Rectangle Sunglasses

    Mood set before the outfit. These chic sunglasses feature a sleek rectangular frame with tinted lenses that instantly sharpen up your off-duty 'fits, coffee runs, and last-minute plans.

    Fit & Features

    • Rectangular-shaped plastic frame
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000111

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Confidence Curved Rectangle Sunglasses

    These curved rectangle sunglasses bring sleek confidence with a lightweight metal frame and polarized tinted lenses that keep everything looking sharp from brunch to beach days.

    Fit & Features

    • Curved rectangular shape
    • Thin metal frame
    • Rubber nose pads
    • Polarized tinted lenses

    Style Number/Barcode: 07008-000112

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Garden Floral Cowl Neck Maxi Dress

    Serving soft glam with a flirty twist. This floral cowl neck maxi dress drapes effortlessly through the neckline and skims the body for a dreamy silhouette made for weddings, vacations, and any dressy event.

    Fit & Features

    • Floral print, knit-lined fabric
    • Cowl neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001147

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Seaside Glamour Crochet Strapless Mini Dress

    Serving seaside glamour. This seashell crochet mini dress hugs in all the right places, with a strapless sweetheart neckline and textured crochet knit, ready for beach clubs, sunset dinners, and every vacation photo moment.

    Fit & Features

    • Sheer crochet knit fabric with lining
    • Seashell embellishments
    • Strapless sweetheart neckline, padded bust
    • Back zipper closure
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000430

    Category Name: Vacation Looks

    Price: $19.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Bold Bloom Floral Knit Midi Tube Dress

    Big blooms, bold plans. This floral knit midi tube dress hugs in all the right places with a sleek bodycon fit and effortless strapless neckline—perfect for brunch dates, rooftop drinks, or any moment that deserves a standout look.

    Fit & Features

    • Ribbed knit fabric, moderate stretch
    • Large floral print
    • Strapless neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000344

    Category Name: Vacation Looks

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Glow Up Thong Wedge Heels

    The kind of heels that glow with each step. These metallic thong wedges give you height without the drama, adding that polished finish to your favorite looks.

    Fit & Features

    • 3" Wedge heel
    • Square toe
    • Thong-style toe strap
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-000040

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twinkle Toes Rhinestone Strappy Sandals

    That subtle shine you only notice up close. These rhinestone strappy sandals are designed to elevate everyday outfits without stealing the spotlight.

    Fit & Features

    • Round toe design
    • Rhinestone-embellished toe and asymmetrical straps
    • Flat sole
    • Luxe fit cushioned insole
    • Smooth faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000066

    Category Name: Vacation Looks

    Price: $20.90

    Availability: In Stock

    Available Color: NUDE

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

  • Untamed Energy Snake Print Swimsuit

    You'll serve bold confidence in this swimsuit before you even hit the water. This snake print one-piece features a lace up front with crisscross straps and a curve-hugging fit that turns every poolside moment into a full look.

    Fit & Features

    • Smooth stretch swim material with snake print pattern
    • Strapless neckline with adjustable straps
    • Lace-up front detail
    • High-cut leg design, cheeky coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000033

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: SNAKE

    Available Size: S, M, L

  • Elevated Thong Platform Wedge Sandals

    The effortless height your outfits have been waiting for. These thong wedge sandals add a sleek lift with a minimal strap design that pairs perfectly with your everyday looks.

    Fit & Features

    • Wedge heel
    • Almond toe
    • Wide thong strap
    • Cushioned insole
    • Platform sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-000039

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hotter Than Summer Bikini Bottoms

    Booked the trip just to wear this. These bikini bottoms serve sculpted support with cheeky coverage and beaded detail, plus adjustable side ties that let you customize the fit before you hit the pool. Style with the matching bikini top.

    Shop Matching Top: Hotter Than Summer Bikini Top

    Fit & Features

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

    Style Number/Barcode: 07105-000041

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: RUST

    Available Size: S, M, L

  • Hotter Than Summer Bikini Top

    Booked the trip just to wear this. This bikini top serves sculpted support with a ruched bust and charm detail, plus adjustable straps that let you customize the fit before you hit the pool. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Hotter Than Summer Bikini Bottoms

    Fit & Features

    • Smooth stretch knit fabric
    • U-wire sweetheart neckline with ruched bust and charm detail
    • Adjustable shoulder straps
    • Back hook closure
    • Minimal coverage fit
    • Runs true to size

    Style Number/Barcode: 07104-000028

    Category Name: Vacation Looks

    Price: $28.90

    Availability: In Stock

    Available Color: RUST

    Available Size: S, M, L

  • Sunset Swirl Lace-Up Maxi Dress

    Serve vacation glow from every angle in this striped maxi dress. This dress hugs your curves while the crisscross lace-up back and flared mermaid hem bring the drama for cocktails and dinners with a view.

    Fit & Features

    • Striped pattern, crochet knit lined fabric
    • V-neckline with tie front detail
    • Spaghetti straps shape the strappy lace-up back
    • Mermaid flared maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000426

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: PINK

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

  • Vacay Sparkle Tropical Sequin Mini Dress

    Booked the trip and packed the drama. This tropical floral sequin tube bodycon mini dress hugs close with a glossy, light-catching finish that was made for sunset cocktails and flash photography.

    Fit & Features

    • Tropical floral, sequin mesh fabric, sewn-in lining
    • Tube strapless neckline, non-slip grip lining
    • Side zipper and hook-eye closure
    • Bodycon mini fit
    • Runs true to size

    Style Number/Barcode: 05102-000427

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Effortless Drama Bodycon Mini Dress

    Giving sultry with a twist, this leopard mini dress knows how to steal the spotlight. The ruffled sash detail takes your bodycon moment to the next level—perfect for parties, dates, or that glam night out.

    Fit & Features

    • Leopard print, mesh-lined fabric, moderate stretch
    • Strapless tube neckline, padded bra cups
    • Bodycon silhouette
    • Mini-length hem, side ruffled sash detail
    • Runs true to size

    Style Number/Barcode: 05103-000859

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: PURPLE

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

  • Siren Vibe Cutout One-Piece Swimsuit

    This swimsuit was made for the kind of beach day that turns into sunset plans. The cutout one-piece swimsuit hugs with smooth stretch knit fabric, a plunging halter neckline, and a bold O-ring detail that keeps the vibe confident and a little daring.

    Fit & Features

    • Smooth stretch knit fabric
    • Abstract tie-dye print
    • Plunging V-neckline, halter strap
    • Center O-ring metal accent
    • Side cutouts leading to open back, tie-back spaghetti straps, high-cut cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000027

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

  • Vanna Payette Sequin Crochet Column Dress

    Special Occasion

    Made for evenings that call for a little extra shimmer, the Vanna payette sequin crochet column dress catches the light with every step. The sleek silhouette is finished with a strappy open back and high-cut side slits, creating an effortlessly striking look from every angle.

    Fit & Features

    • Sheer crochet knit fabric with mesh lining, moderate stretch
    • All-over payette sequin embroidery
    • Sleeveless V-neckline
    • Spaghetti straps with beading and seashell accents, open cross-back strappy design
    • Dual high side slits
    • Floor-length column silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, bridal celebrations, honeymoons, birthday dinners, anniversaries, formal parties, and vacations.

    Style Number/Barcode: 05002-001099

    Category Name: Vacation Looks

    Price: $29.97 $79.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, M, L, XL

    Product Badge:
    • Sale
  • Vacation Coded Floral Maxi Dress

    This tropical floral print maxi drapes in airy mesh with a soft cowl neck and lace-up back, flowing into a floor grazing hem that moves like you planned this getaway all along. Perfect for weekend and long getaways, where the sun will shine on you in this gorgeous dress!

    Fit & Features

    • Tropical floral print, mesh fabric, soft knit lining
    • Cowl neck, spaghetti straps
    • Lace-up back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000990

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XL

    Product Badge:
    • Sale
  • Wild Plans Animal Print Mesh Halter Mini Dress

    Wild plans call for a dress that knows exactly what it’s doing. This animal print mesh halter mini dress hugs through the waist with ruched shaping and flares out with playful tiers that move with you from dinner reservations to wherever the night decides to go.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Animal print
    • Sleeveless halter neckline with tie-back straps, partially open back
    • Metal hardware accent, keyhole bust cutout
    • Ruched drop waist
    • Tiered ruffled design, mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-000350

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Radiant Shine Tube Mini Dress

    Like sunshine you can wear. This glitter mesh tube mini dress features a soft A-line shape that gives a flattering, flirty fit while the subtle shimmer catches the light for brunch plans, vacations, and warm night outings.

    Fit & Features

    • Glitter mesh fabric, soft knit lining
    • Strapless tube neckline
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000732

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Impact Floral Mesh Maxi Dress

    This floral mesh halter maxi dress features a draped cowl neckline and curve-hugging silhouette that flows into a sleek maxi length, perfect for date nights, vacations, and dressy events.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Cowl halter neckline
    • Open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000683

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS

  • Sweet Citrus A-Line Mini Dress

    Like sunshine in outfit form. This lemon print stretch linen mini dress features a square neckline with a delicate bust tie and a flirty A-line skirt that’s made for brunch dates, vacations, and sunny day plans.

    Fit & Features

    • Citrus print, cotton-blend woven fabric, woven lining
    • Square neckline with tie front
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • A-line fitted silhouette, pipe trim
    • Flared mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000518

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Fresh Blooms Puff Sleeve Skater Dress

    Cute plans start with a dress like this. This floral skater dress features a sweetheart neckline with a flirty tie detail and an open back design that feels perfect for brunch dates, Easter, and sunny weekend plans.

    Fit & Features

    • Floral vineyard print, linen-like fabric with woven lining
    • Sweetheart neckline with tie front detail
    • Puff short sleeves with elastic cuffs
    • Strappy lace-up back design
    • Flowy skater short silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000914

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE-2

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

    Product Badge:
    • Sale
  • Sunny Days Strappy Platform Wedges

    These wedges understood the assignment. Strappy knotted details, and a cork platform wedge give you that easy lift while keeping the vibe effortless for brunch plans, coffee shops, or warm weather getaways.

    Fit & Features

    • 4" Wedge heel
    • Square toe, strappy design
    • Platform sole
    • Luxe fit cushioned insole
    • Adjustable ankle strap with buckle closure
    • Cork/ faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-000031

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 7.5, 8, 8.5, 10

    Product Badge:
    • Best Seller
  • Casual Cutie Platform Thong Wedges

    Your everyday flip-flop just got an upgrade. These platform thong wedge sandals give you a clean, minimal look with extra height and an easy slip-on fit that works from coffee runs to weekend plans.

    Fit & Features

    • Wedge heel
    • Square toe
    • Wide thong toe strap
    • Wedge platform sole
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-000038

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free