Vacation Looks

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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.

  • Gimme The Flare Denim Jumpsuit

    Give your closet a trendy upgrade in this essential denim jumpsuit perfect for hitting up the farmer's market or grabbing brunch with friends! It features short sleeves, a collar neckline, button-down front closures, four-pocket styling, belt loop accents, and a hip-hugging flare-leg silhouette. Complete the look in peep toe booties.

    Fit & Features

    • Short sleeves
    • Collar neckline
    • Button-down front closures
    • Four-pocket styling, belt loop accents
    • Hip-hugging, flare-leg silhouette
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0366

    Category Name: Vacation Looks

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Boho Chic Straw Platform Block Heels

    Platform and boho chic, these block heels were made for fun under the sun! Pack these essential shoes for vacations, weekend trips, or a beach day. They feature an almond toe, an adjustable ankle strap with buckle closure, and a platform sole to elevate the style. Complete the look with the matching hat and bag!

    Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
    Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
    Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote Bag

    Fit & Features

    • 3.5" Block heel
    • Almond toe
    • Adjustable ankle strap, buckle closure
    • Platform sole
    • Luxe fit cushioned insole
    • Straw material
    • Runs true to size

    Style Number/Barcode: 07401-4659

    Category Name: Vacation Looks

    Price: $20.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Irresistibly Sweet V-Neck Floral Chiffon Maxi Dress

    You'll be irresistibly sweet in this floral chiffon maxi dress at showers, graduations, or semi-formal events! The V-neckline and spaghetti strap tie accentuate your frame while the flowy maxi silhouette adds a touch of elegance. With a front slit and floor-length hem, this dress is perfect for any occasion. Complete the look in espadrille wedges.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • V-neckline
    • Spaghetti strap ties
    • Front slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3301

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Mood Rectangle Sunglasses

    Top off your summer 'fits and bring that bold flair with these trendy rectangle sunglasses! These cool shades feature a rectangular-shaped design with a thick plastic frame, wide arms, built-in nose pads, and tinted lenses. Style with strappy sandals.

    Fit & Features

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

    Style Number/Barcode: 07008-1077

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Forward Strappy Back Skater Dress

    Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone!

    Fit & Features

    • Woven fabric with woven lining
    • Square neckline with bust tie
    • Spaghetti straps
    • Strappy tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3684

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: M, L, XXS

    Product Badge:
    • Sale
  • Sassy Sweet Floral Chiffon Ruffled Skater Dress

    Sassy and sweet, this floral chiffon skater dress will be your new brunch go-to! The strapless smocked bodice and ruffled skater silhouette are feminine details you'll adore.

    Fit & Features

    • Chiffon fabric, stretchy knit lining
    • Small floral print
    • Strapless straight neckline
    • Smocked bodice
    • High waist seam
    • Tiered ruffled design, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5967

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Get Cutesy Faux Leather Sherpa Bucket Hat

    Get cutesy with your outfit in this faux leather bucket hat perfect for bringing the cozy vibes! The hat features a classic bucket hat styling with a faux sherpa trim. Complete the look in a cozy jacket on a chilly day!

    Fit & Features

    • Faux leather exterior
    • Classic bucket hat styling
    • Faux sherpa trim

    Style Number/Barcode: 07302-1488

    Category Name: Vacation Looks

    Price: $3.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Open Cable Knit Halter Top

    The weekend is calling, and this cable knit top is here to make you stand out from any crowd! It boasts a flattering high halter neckline and open back with dual ties for a head-turning allure.

    Fit & Features

    • Cable knit fabric
    • High halter neckline
    • Open back with dual tie backs
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06005-2293

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Posh And Pretty Strapless Bow Ponte Crop Top

    You'll draw everyone will this posh and pretty ponte crop top! Designed with a sleek strapless neckline and front bows with cutouts, this top will turn heads.

    Fit & Features

    • Ponte knit fabric
    • Strapless neckline
    • Front bows with cutouts
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000124

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Quite A Bell Sleeve Crop Sweater

    Your new favorite crop sweater to create all sorts of trendy outfits! It features long bell sleeves, a mock neck, and a center front slit accent, and is composed of a rib-knit fabric with minimal stretch. Style with flare denim jeans to complete the look.

    Fit & Features

    • Long bell sleeves
    • Mock neck
    • Center front slit accent
    • Cropped hem
    • Sweater rib-knit fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1812

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Sunny Scoop Neck Skater Eyelet Mini Dress

    Sunshine days are ahead and this skater mini dress is perfect for enjoying the weekend and weather! Crafted from an adorable eyelet knit fabric, this mini dress is designed with a flattering scoop neckline, adjustable spaghetti straps for a perfect fit, and a flirty tie-back detail to show off your style. The skater silhouette and tiered ruffled hem allow for movement and a fashionable sway with every step! Complete the look in heeled sandals.

    Fit & Features

    • Eyelet knit fabric, sewn-in knit lining
    • Adjustable spaghetti straps
    • Tie-back detail
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5426

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Style Woven Tie-Waist Wide-Leg Pants

    Capture that coastal-chic style with these breezy tie-waist wide-leg pants. Designed with an airy lightweight woven fabric, they feature a high-rise waist with an elasticized back waistband for added stretch, a side tie accent, and a flowy wide-leg silhouette. Pair with a basic crop top and strappy sandals.

    Fit & Features

    • Airy woven fabric, no stretch
    • High waist, elasticized back waistband
    • Side tie detail
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06402-1409

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stop and Stun Floral Slit Maxi Dress

    Serving petal power with every step. This floral print maxi stuns with a draped cowl neckline and a high front slit that brings the drama (and the legs).

    Fit & Features

    • Floral print, mesh-lined fabric
    • Cowl neckline
    • Spaghetti straps
    • Form-hugging fit
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000348

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S

  • Traveling Cute Halter Wide-Leg Cargo Jumpsuit

    Travel cute wherever you're heading in this sleeveless woven jumpsuit for a chic and polished vibe! The halter collar neckline and front zipper closure provide a classic and utility touch, while the open back with an adjustable strap flaunts some skin, and side and flap pockets offer functionality along the wide-leg silhouette. Complete the look with a trendy shoulder handbag.

    Fit & Features

    • Woven fabric
    • Front zipper closure
    • Open back, adjustable strap
    • Side pockets, flap pockets
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1407

    Category Name: Vacation Looks

    Price: $24.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Effortless Tie-Front Ruffled Skater Dress

    Make your weekend outfits so effortless with this adorable tie-front skater dress. The lightweight gauze fabric paired with the ruffled skater silhouette creates that breezy, flowy fit you'll love.

    Fit & Features

    • Gauze woven fabric with smooth woven fabric, no stretch
    • Sleeveless V-neckline, padded bust, bust tie accent, keyhole cutout
    • Adjustable spaghetti straps
    • Partially smocked back
    • High waist seam
    • Short skater silhouette, tiered ruffled design
    • Runs true to size

    Style Number/Barcode: 05102-6028

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: OLIVE

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

  • Now In Bloom Open Back Floral Maxi Dress

    A sultry open back you'll adore with chic floral blooms! This maxi dress captures attention with its flattering cowl neckline and curve-hugging silhouette, perfect for shower celebrations and dressy events!

    Fit & Features

    • Floral print, mesh-lined fabric
    • Cowl neckline
    • Spaghetti strap ties
    • Open back
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000023

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Vibes Faux Sherpa Shacket

    Layer on all the cozy vibes with this trendy faux sherpa shacket! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, side pockets, and a relaxed oversized fit for that ultra-comfy feel. The soft faux sherpa fabric includes a cotton-blend lining. Pair this adorable shacket over a basic bodysuit with faux leather leggings and combat boots!

    Fit & Features

    • Collared neckline
    • Long sleeves, single button detail
    • Complete button-down front
    • Dual buttoned chest pockets
    • Dual lined side pockets
    • Faux sherpa fabric, cotton-blend lining, minimal stretch
    • Relaxed oversized fit

    Style Number/Barcode: 06201-0408

    Category Name: Vacation Looks

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dainty Cubic Zirconia Evil Eye Charm Necklace

    Radiate and sparkle with positive energy in this delicate evil eye charm necklace! It features a dainty chain with an evil eye charm embellished with mini cubic zirconia stones and beaded detailing for a pretty vibe. Style with hoop earrings and strappy sandals.

    Fit & Features

    • Dainty chain
    • Evil eye charm
    • Mini cubic zirconia stones, beading
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1777

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Simplicity Open-Circle Charm Necklace

    Effortlessly elevate your looks with this sleek charm necklace, a chic simple accessory for every day. It features a dainty chain with a delicate open circle charm at the center. Style with hoop earrings.

    Fit & Features

    • Dainty chain-link design
    • Center open-circle charm
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1807

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Boho Halter Open Back Knit Top

    Create a boho babe vibe in this sleeveless knit top with a plunging halter neckline, open back, and a trendy front crochet flyaway design. Style with the matching hot shorts for festival season!

    Shop Matching Bottoms: Feelin' Boho Scallop Hem Knit Hot Shorts

    Fit & Features

    • Sweater knit fabric
    • Sleeveless plunge halter neckline, tie-back straps
    • Open back, lower tie-back straps
    • Front crochet flyaway design
    • Mid-length hem, flowy fit
    • Runs true to size

    Style Number/Barcode: 06005-2256

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Second Look Turtleneck Open Back Sweater

    This cozy crop sweater will make everyone do a double-take! Featuring slouchy long sleeves with ribbed cuffs, a turtle neckline, and a cute surplice open back design on a relaxed silhouette on ultra-soft knit fabric. Complete the look in a mini skirt and your favorite boots for a coffee date or pumpkin patch.

    Fit & Features

    • Long sleeves, ribbed cuffs
    • Turtle neckline
    • Surplice open back
    • Relaxed silhouette, cropped hem
    • Ultra-soft rib knit sweater fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1744

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Floral Sweetheart Bodycon Mini Dress

    Step out in this flirty floral mini dress for Valentine's Day, dates, and parties! Showcasing a ditsy floral print on soft brushed knit fabric, this dress features a bust tie keyhole, side ruching, and a bodycon fit, to accentuate your figure. Complete the look with a mini purse and heels.

    Fit & Features

    • Ditsy floral print, brushed knit fabric with stretch
    • Spaghetti straps
    • Bust tie keyhole
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5523

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Bliss Tie-Back Slit Maxi Dress

    Ideal for making a statement at any occasion, this artsy print maxi dress combines chic with effortless style. Featuring a flattering A-line silhouette and a stylish front slit, this dress offers a breezy look that turns heads with a tie-back design.

    Fit & Features

    • Artsy print, woven fabric, stretchy knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Tie-back design
    • A-line silhouette
    • Front slit, flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6039

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Amalfi Coast Plunge Neck Mermaid Floral Maxi Dress

    Enjoy a sunset dinner and drinks in this floral maxi dress along the Amalfi Coast! With sultry details and a mermaid silhouette that flaunts your curves, this dress will turn heads.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Plunge halter cowl neckline, tie closure
    • Mermaid silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000302

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BURGUNDY

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