Vacation Looks

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STYLE SPOTLIGHT

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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.

  • Too Cool Contrast Trim Faux Leather Sneakers

    These faux leather sneakers are too cool for school! Kick back in these exclusive shoes featuring a round toe and lace-up placket for a perfect fit. A cool contrast trim for added style and a comfortable footbed and rubber insole. Complete the look with a zip-up hoodie for casual plans.

    Fit & Features

    • Round toe
    • Lace-up placket
    • Contrast trim
    • Comfortable footbed
    • Rubber insole
    • Runs true to size

    Style Number/Barcode: 07407-0225

    Category Name: Vacation Looks

    Price: $28.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One Short Day Linen High-Rise Ruffle Mini Skirt

    Easy and effortless, this linen mini skirt boasts a playful vibe with a ruffled hem perfect for sunny-day dressing!

    Fit & Features

    • Linen-blend woven fabric, sewn-in knit lining
    • High-rise waist
    • Side zipper and hook-eye closure
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06301-000003

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Wild Intentions Cutout Mesh Mini Dress

    Giving an island goddess with a hint of chaos—in the best way. The bodycon fit and hoop cutout bring the heat, while the ruffle-trim slit? Pure drama.

    Fit & Features

    • Mesh-lined fabric with leopard multi-print
    • Cowl halter neckline with spaghetti straps
    • Side cutout with hoop insert detail
    • Bodycon fit with asymmetric ruffle-trim slit
    • Mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000144

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: L

  • Iconic Style High-Rise Cut-Off Denim Shorts

    These iconic denim shorts will forever be a flattering staple in your closet! The high-rise waist provides a flattering and comfortable fit, while the frayed hem adds a touch of edginess.

    Fit & Features

    • Medium wash denim, non-stretch
    • High-rise waist
    • Frayed hem
    • Front five-button fly closures
    • Five-pocket styling, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000001

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: MED, DENIM

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

  • Casual Scene Crew Neck Midi Dress

    Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.

    Fit & Features

    • Crew neck, short sleeves
    • Cutout waist, knot accent
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Smooth cotton knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5765

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get The Look Crochet High-Rise Pants

    Curate effortless vibes in these crochet high-rise pants, perfect for pairing with the matching top for a cute look!

    Fit & Features

    • Embroidered crochet fabric, sewn-in panty knit lining
    • High-rise waist, side zipper and hook-eye closure
    • Sheer design
    • Runs true to size

    Shop The Matching Top: Get The Look Crochet Halter Crop Top

    Style Number/Barcode: 06402-000005

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sweet Escape Lace-Up Tropical Midi Dress

    Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical print, lined knit fabric, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Asymmetric high-cut hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5564

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Muse Floral Eyelet Chiffon Romper

    You'll be a total sunny muse in this adorable romper made with airy eyelet chiffon fabric and a dainty floral print pattern. The sweetheart neck features a lace-up bust design, leading to the cutest fit-and-flare silhouette with flowy shorts.

    Fit & Features

    • Sheer eyelet chiffon fabric with floral print, stretchy knit lining
    • Sleeveless sweetheart neckline, lace-up bust, padded bra cups
    • Adjustable spaghetti straps
    • Smocked back, zipper hook-eye closure
    • High-rise seam
    • Flowy shorts, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 06403-000008

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Luxe Flair Woven Loop Satin Scarf

    Add a luxe flair to your spring and summer 'fits with this woven loop satin scarf! Designed with a silky satin material with a chic woven loop pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with chunky gold hoop earrings.

    Fit & Features

    • Non-stretch satin material
    • Woven loop pattern

    Style Number/Barcode: 07305-0491

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Western Showdown Etched Concho Belt

    Saddle up with this playful etched concho belt, featuring an adjustable lobster clasp closure. Wrangle up some Western vibes and complete the look in denim shorts for a festival or concert!

    Fit & Features

    • Etched concho belt
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1113

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • Best Seller
  • Chic Breeze Chain Printed Satin Scarf

    Add a luxe flair to your spring and summer 'fits with this woven chain-printed satin scarf! Designed with a silky satin material with a chic woven chain pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with high-rise denim shorts.

    Fit & Features

    • Satin chain printed woven scarf
    • Multiple styling options

    Style Number/Barcode: 07305-0500

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Vibes High Slit Woven Midi Skirt

    This airy woven midi skirt will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric with a mini-length lining, it features a high waist with the cutest tie detail, a high-cut side slit to showcase some leg, and a flowy slim-fit silhouette. Style with the matching crop top for a fabulous 'fit!

    Shop Matching Orange Top: Sunny Vibes Bow Back Woven Crop Top

    Fit & Features

    • Woven fabric with mini-length knit lining, minimal stretch
    • High-rise elasticized waist
    • Tie detail
    • High side slit
    • Flowy slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 06401-0651

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seas The Day Shell Stud Earrings

    A little coastal charm, a lot of main character energy. These seashell studs are the perfect vibe for vacay fits, beach days, or cute mermaid moments.

    Fit & Features:

    • Mini seashell design with polished finish
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000126

    Category Name: Vacation Looks

    Price: $8.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Chasing The Sun Banner Woven Satin Scarf

    Chase this sun banner silky woven scarf for the perfect look for your next sweet escape! Designed with a silky satin material with a chic sun banner pattern, this sleek scarf offers multiple styling options. Tie it around your neck for a fab accent, as a headwrap, or a trendy hair tie! Pair with a sultry jumpsuit.

    Fit & Features

    • Sun banner print
    • Woven satin fabric
    • Multiple styling options

    Style Number/Barcode: 07305-0499

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Sleek Cross Concho Chain Belt

    Sleek and trendy, this cross concho chain belt radiates boho-chic vibes. Style over a lace skirt with knee-high boots.

    Fit & Features

    • Cross and concho textured metal design
    • Center stone embellishments
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07301-000043

    Category Name: Vacation Looks

    Price: $16.90

    Availability: In Stock

    Available Color: BLACK/GOLD

    Available Size: NS

    Product Badge:
    • Sale
  • Wrapped In Power Snake Bracelet

    Ssshe’s not your average accessory! This snake wrap bracelet slithers on with attitude—bold, edgy, and ready to strike a statement. Stack it or let it steal the show solo.

    Fit & Features

    • Smooth, flexible wrap-around design
    • Snakehead and tail detailing with engraved texture
    • Sculpted metal finish 
    • Adjustable styling

    Style Number/Barcode: 07003-000024

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Free Riders Colored Stone Chain Belt

    Accessorize your ride with this statement western chain belt featuring unique colored stones, oval-shaped charms, and an adjustable lobster clasp closure to secure the style. Complete the look in a fitted mini dress.

    Fit & Features

    • Colored stones
    • Oval-shaped charms
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1146

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle Me Up Crop Top

    Flirty, flowy, and made for vacay vibes! This ruffle-trim crop top brings soft drama with a sleek fit and tie-front design that shows just enough—pair it with the matching skirt to complete the look.

    Shop The Matching Skirt: Ruffle Me Up Midi Skirt

    Fit & Features

    • Smooth double-lined stretchy knit fabric
    • Ruffled trim front
    • Tie front closure
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06202-000040

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: PINK

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

    Product Badge:
    • Part of a Set
  • Tropic Time Halter Cutout Wide-Leg Jumpsuit

    Bring on the summer weather in this tropical wide-leg jumpsuit for your next vacation or any weekend plans! This eye-catching jumpsuit features a flattering halter neckline and strategic cutouts that accentuate your curves. 

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Halter neckline with spaghetti strap ties
    • Cutout bodice
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000013

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Boardwalk Crop Denim Jacket

    Stroll the boardwalk before your sunset dinner in this streetwear-inspired crop denim jacket featuring long sleeves with buttoned cuffs, a collared neckline, four-button front closure, flap pockets, distressed accents, and a pull tab button closure along the hem. Complete the look in breezy wide-leg pants and a bodysuit.

    Fit & Features

    • Non-stretch denim fabric
    • Long sleeves, buttoned-cuffs, collared neckline
    • Four-button front closure
    • Flap pockets, buttons
    • Distressed accents
    • Pull tab button closure along crop hem
    • Runs true to size

    Style Number/Barcode: 06203-0540

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Cute to Pleat Strapless Romper

    Low effort, high impact. This strapless lace romper accentuates the waist and flares with pleated drama—aka, your new going-out obsession.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Strapless neckline
    • Pleated mini-length hem
    • Shorts lining with mesh lace trim
    • Runs true to size

    Style Number/Barcode: 06503-000096

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Double Trouble Snake Chain Lariat Necklace Set

    Two chains, one goal—steal the spotlight. This snake chain lariat necklace set is your new go-to for stacking drama and drip, whether you’re out for dinner or just feelin’ yourself in selfies.

    Fit & Features

    • Two-pack necklace set
    • Short snake chain
    • Longer snake chain, triangle-shaped center accent, long lariat design
    • Back lobster clasp closures with extenders

    Style Number/Barcode: 07002-000026

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cubic Zirconia Studs Set

    Glam up your look with this cubic zirconia stud earrings set. This pack of six varying-sized studs gives you the option of how much bling you want to rock for the day. Perfect to dress up an everyday outfit to go run errands. Pair with a chic bodysuit and distressed denim and you'll be all ready to go!

    Fit & Features

    • Cubic zirconia
    • Post-back closures, rubber stoppers
    • Set of six studs

     

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

    Style Number/Barcode: 07001-3731

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • When Life Gives You Lemons Tote Bag

    Carry summer vibes everywhere with this canvas tote bag! This eye-catching canvas tote features a vibrant lemon print that adds a refreshing pop to any outfit while providing plenty of space for your must-haves.

    Fit & Features

    • Top handles
    • Lemon print design
    • Spacious interior
    • Canvas material

    Style Number/Barcode: 07203-000026

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free