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.

  • Center Of It All Cowl Neck Maxi Dress

    You don’t need an introduction in this one. This cowl neck maxi dress drapes just right with a curve-hugging fit and open back that feels both bold and effortless.

    Fit & Features

    • Sleek knit fabric, high stretch
    • Sleeveless plunging cowl neckline
    • Halter tie-back spaghetti straps
    • Thin metal O-ring hardware accents
    • Open back
    • Maxi-length bodycon silhouette, back slit detail
    • Runs true to size

    Style Number/Barcode: 05101-000880

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, L

  • Gallery Date Floral Midi Dress

    This floral midi dress skims your shape with a cowl neckline and lace-up back, made for brunches, showers, and any dressy occasion you feel like showing up styled.

    Fit & Features

    • Artsy floral print, woven fabric, crepe lining
    • Cowl neckline
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Lace-up back ties
    • Side slit
    • Curve-hugging, midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001410

    Category Name: Vacation Looks

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple Charm Gingham Mini Dress

    Feels like a picnic invite just showed up. This gingham mini dress keeps it cute and easy with a collar, cap sleeves, and a button-down front that works from coffee shop hangs to casual plans.

    Fit & Features

    • Gingham pattern, cotton-blend woven fabric, woven lining
    • Collar neckline
    • Cap sleeves
    • Front button-down closures
    • Tie-back strap
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000598

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Playful Plans Flamingo Earrings

    Your outfit just found its personality. These flamingo statement earrings bring sparkle, feathers, and full-on fun to any occasion.

    Fit & Features

    • Teardrop rhinestone
    • Rhinestone-embellished flamingos with faux feathers
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000380

    Category Name: Vacation Looks

    Price: $16.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Flirt Mode Ruffle Mini Skort

    A little sweet, a little bold—this one knows exactly what it’s doing. The ruffle mini skirt is fitted and flares out with a ruffle detail that keeps it playful from brunch plans to late dinners. Style with the matching tie-front top.

    Shop Matching Top: Flirt Mode Ruffle Sleeve Tie-Front Top

    Fit & Features

    • Sleek knit fabric, high stretch
    • High-rise waist, ruched detailing
    • Tiered ruffled design
    • Mini-length overlay, fitted A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000282

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Easy Does It Linen Tie-Front Top

    The perfect top for effortless dressing. This easy, breezy tie-front linen top features dramatic, long bell sleeves that move with you during vacations or weekend getaways.

    Fit & Features

    • Linen-blend woven fabric
    • Tie-front neckline
    • Long bell sleeves
    • Fitted crop elasticized hem
    • Runs true to size

    Style Number/Barcode: 06204-000127

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Vacation Calling Floral Mesh Mini Skirt

    This mini skirt says beachside drinks, sunset photos, and a dinner with a view. It features a high-rise waist with a bodycon silhouette and mini-length hem that flaunts your figure. Style with the matching poncho.

    Shop Matching Top: Vacation Calling Floral Mesh Poncho

    Fit & Features

    • Mesh knit fabric, tropical floral print, high stretch
    • High-rise waist
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000136

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Vacation Calling Floral Mesh Poncho

    This poncho says beachside drinks, sunset photos, and a dinner with a view. It features an asymmetric neckline and a flowy, relaxed poncho silhouette with a crop length that flaunts your figure. Style with the matching mini skirt.

    Shop Matching Bottoms: Vacation Calling Floral Mesh Mini Skirt

    Fit & Features

    • Mesh knit fabric, tropical floral print, high stretch
    • Asymmetrical neckline
    • Relaxed poncho silhouette
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000095

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS/S, M/L

    Product Badge:
    • Part of a Set
  • Buckle Up Belted Studded Denim Mini Skort

    Not your basic mini skort—this one comes with attitude. The denim mini skort cinches with a belted accent and flares out with pleated detailing, giving you that effortlessly styled look. Style with the matching tube top.

    Shop Matching Top: Buckle Up Denim Belted Tube Top

    Fit & Features

    • Denim fabric with distressed details
    • Mid-rise waist, belted accent
    • Drop waist design
    • Nailhead-studded detailing
    • Mini-length pleated overlay, A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06603-000184

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BEIGE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Coast Along Espadrille Wedges

    Booked the plans just so you could wear these. These strappy espadrille wedges bring that effortless vacation feel with a lifted sole and barely-there straps that add a cute touch to every outfit.

    Fit & Features

    • Wedge heel
    • Square toe
    • Strappy design
    • Platform espadrille sole
    • Adjustable ankle strap with buckle closure
    • Faux leather upper
    • Runs true to size

    Style Number/Barcode: 07406-000060

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 8.5, 10, 11

    Product Badge:
    • Best Seller
  • Sunshine Fine Straw Block Heels

    Step into sunshine in these straw block heels with a trendy strappy design, perfect for styling with a flowy maxi dress or skirt!

    Fit & Features

    • 4" Block heel
    • Almond toe
    • Strappy design
    • Adjustable ankle strap, buckle closure
    • Luxe fit cushioned insole
    • Straw faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000005

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: NATURAL

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

  • Poolside Plans Jelly Kitten Heels

    Vacation mood activated. These jelly kitten heels bring a playful throwback feel with clear thong straps and an easy slip-on design made for sunny day dressing!

    Fit & Features

    • Kitten heel
    • Square toe
    • Clear PVC thong strap
    • Cushioned insole
    • Jelly material
    • Runs true to size

    Style Number/Barcode: 07401-000707

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: TURQUOISE

    Available Size: 10

  • Serving Attitude Striped Knit Hot Shorts

    Serving shape and attitude in one effortless vibe. These striped knit hot shorts hug your body with a soft, stretchy feel made for last-minute plans that somehow turn iconic. Style with the matching halter top.

    Shop Matching Top: Serving Attitude Striped Knit Halter Top

    Fit & Features

    • Striped ribbed knit fabric, high stretch
    • Mid-rise waist
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06503-000254

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Serving Attitude Striped Knit Halter Top

    Serving shape and attitude in one effortless vibe. This striped knit halter top hugs your body with a soft, stretchy feel made for last-minute plans that somehow turn iconic. Style with the matching hot shorts.

    Shop Matching Bottoms: Serving Attitude Striped Knit Hot Shorts

    Fit & Features

    • Striped ribbed knit fabric, high stretch
    • Sleeveless V-neckline
    • Halter strap
    • Partially open back
    • Form-hugging fit
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000333

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: M, L

    Product Badge:
    • Part of a Set
  • Island Crush Flower Two-Pack Hair Clips

    Serving vacation pics even when you’re just running late to brunch. These two-pack flower hair clips add the cutest little pop to messy buns, slick backs, and beach day waves!

    Fit & Features

    • Two-pack hair clip set
    • Tropical floral design
    • Clip closure

    Style Number/Barcode: 07006-000132

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

  • Serving Sculpted Cutout Midi Tube Dress

    Serving sculpted and a little daring—this cutout midi tube dress knows how to hold attention. The ribbed knit hugs in all the right places while the cutout O-ring detail adds that extra edge for nights you’re not playing it safe.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Strapless straight-across neckline
    • Front waist cutout, metal O-ring hardware accents
    • Midi-length hem, high-cut side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000334

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Flirty Vibes Strapless A-Line Mini Dress

    This is your flirty little upgrade when you want to feel instantly put-together. The strapless A-line mini dress hugs up top, skims the body, and finishes with a playful ruffle that moves with you.

    Fit & Features

    • Brushed knit fabric, high stretch
    • Strapless sweetheart neckline
    • Drop waist, ruched detailing
    • Tiered ruffled design
    • Mini-length hem
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000697

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Sweet Charm Flower Strap Crochet Mini Dress

    Serving shape with a side of charm. This crochet mini dress hugs your curves while the flower strap detail brings just enough sweetness—wear it when you want compliments without trying.

    Fit & Features

    • Crochet knit fabric with knit lining, moderate stretch
    • Lettuce edge trims
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, front flower accents
    • Mini-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000318

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Vacay State Of Mind Tropical Print Maxi Dress

    Vacation state of mind, no passport required. This tropical print maxi dress hugs you in all the right places with a sleek bodycon fit and bold cutout details that feel both effortless and elevated.

    Fit & Features

    • Knit fabric with high stretch, soft knit lining
    • Tropical print
    • Strapless neckline
    • Triple bust cutouts and oval-shaped hardware accents
    • Maxi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000622

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Vacay Mood Tropical Floral Halter Skater Dress

    Booked, busy, and dressed like it. This tropical floral halter skater dress hugs just enough up top, then flares into a playful, twirl-ready silhouette made for plans that don’t end early.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Tropical floral print
    • Sleeveless plunging V-neckline, bar strap with beaded accents
    • Halter tie-back straps
    • Open back, lower tie-back spaghetti straps
    • Tiered ruffled design, mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000674

    Category Name: Vacation Looks

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Glow A-Line Midi Tube Dress

    Sunshine, but make it wearable. This A-Line midi tube dress hugs through the ruched bodice, then flows into an effortless, breezy silhouette that’s made for everything from brunch plans to last-minute invites.

    Fit & Features

    • Sleek knit fabric, high stretch
    • Strapless straight-across neckline
    • Fitted ruched bodice
    • Maxi-length flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000722

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Just Enough Drama Slit Maxi Dress

    Float in, leave an impression—no extra effort needed. This maxi dress features a V-neck halter and open back with a high front wrap slit that moves effortlessly at weddings, award nights, and every dressy occasion!

    Fit & Features

    • Smooth knit fabric with stretch
    • Halter V-neckline with tie straps
    • Open back
    • High front wrap slit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001326

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Sofia Linen Halter Mini Dress

    Special Occasion

    Polished with a playful edge, the Sofia linen-blend mini dress is made for those effortlessly chic arrivals that still turn heads. The scallop-contrast trim halter-strap neckline and curve-hugging silhouette create a striking allure, while the mini-length hem is perfect for outdoor soirees. 

    Fit & Features

    • Linen-blend cotton fabric, sewn-in knit lining
    • Contrast trim, scallop halter tie strap neckline
    • Back zipper and hook-eye closure
    • Contrast trim throughout
    • Curve-hugging, scallop mini-length hem
    • Runs true to size

     

    Where to Wear:

    Graduations, garden parties, brunches, milestone celebrations, vacations, resorts, honeymoons, dressy occasions

    Style Number/Barcode: 05001-000772

    Category Name: Vacation Looks

    Price: $89.90

    Availability: In Stock

    Available Color: KHAKI

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Hot Weather Plans Strapless Maxi Dress

    Serving sunshine with zero effort. This strapless bodycon dress hugs in all the right places with a bold floral moment that makes getting dressed for vacations or weekend plans easy.

    Fit & Features

    • Tropical floral print, stretchy knit-lined fabric
    • Strapless tube neckline
    • Bodycon maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000721

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: ORANGE

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