Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • Full Of Trendiness High-Rise Fray A-Line Maxi Skirt

    Your summer is sure to be full of trendiness with this high-rise maxi skirt perfect for weekend plans! Featuring a high-rise waist and unique A-line silhouette with frayed trim, this skirt is made from soft and comfortable cotton woven fabric. Complete the look in an off-the-shoulder blouse and booties!

    Fit & Features

    • Cotton woven fabric, slight stretch
    • High-rise waist
    • Hidden side zipper and hook-eye closure
    • Frayed A-Line silhouette
    • Maxi-length
    • Runs true to size

    Style Number/Barcode: 06301-0192

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hidden Gem Lace-Up Halter Crop Top

    Uncover this cute crop top for the perfect summer look! Featuring a sultry string lace-up halter and a flattering split center design, this crop top will make you stand out in any crowd.

    Fit & Features

    • Stretchy rib knit fabric
    • String lace-up plunge halter neckline
    • Split center accent
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2283

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L

  • Seasonal Treat Chenille Crop Sweater

    Your new go-to chenille sweater for the fall to winter months is here! It features slouchy long sleeves, ribbed cuffs and crew neck, a relaxed silhouette, and cropped hem with dual asymmetrical slit accents. Complete the look in high-rise jeans for looking at Christmas lights!

    Fit & Features

    • Slouchy long sleeves
    • Ribbed cuffs and crew neckline
    • Relaxed silhouette
    • Cropped hem, asymmetrical slit accents
    • Chenille knit fabric
    • Soft and comfortable
    • Fits true to size

    Style Number/Barcode: 06005-1574

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Showstopper Cutout Ruffle Slit Maxi Dress

    Serve major allure in this sleeveless maxi dress while on vacay or weekend getaway! The maxi dress delivers a sultry design with a twist plunge V-neckline, cutout bodice, and a high front slit with a ruffled trim.

    Fit & Features

    • Slinky knit fabric, short knit lining
    • Plunge twist V-neckline
    • Shoulder straps, one metal accent piece
    • Cutout bodice
    • High front slit with ruffle trim
    • Bodycon maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000503

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Natural Attraction Ditsy Floral Mini Dress

    You're sure to have a natural attraction to this ditsy floral mini dress - perfect for a casual birthday or afternoon tea! It features a sleeveless scoop neck, spaghetti straps, a flirty tie front, and ruched bust, and a bodycon silhouette. Style with lace-up heels for a statement finish!

    Fit & Features

    • Sleeveless scoop neck
    • Spaghetti straps
    • Tie front and ruched bust
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print, smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4938

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edge It Up Faux Leather Biker Boots

    Edge up your fall 'fits with this pair of trendy faux leather biker boots. They feature an above-the-ankle height with a square toe, dual straps with buckle accents, a low block heel for comfortable wear, and are made from a smooth faux leather material. Style these biker boots with a bomber jacket and hoop earrings.

    Fit & Features

    • Above-the-ankle height
    • Square toe
    • Dual buckled straps
    • Low block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1718

    Category Name: Vacation Looks

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coastal Chic Linen Halter Maxi Dress

    Meet your vacay soulmate. This breezy maxi serves minimal effort with major impact thanks to its sleek halter neckline, open tie back, and flowy fit made for golden hour strolls or rooftop cocktails.

    Fit & Features

    • Linen-blend woven fabric
    • High halter neckline, spaghetti strap tie
    • Open back with spaghetti strap tie, lower zipper and hook-eye closure
    • High side slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000026

    Category Name: Vacation Looks

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S

    Product Badge:
    • Sale
  • Catch Me Twirlin' Ruffle Chiffon Skater Dress

    One spin and you're giving main character energy! With dreamy chiffon ruffles, sweet side cutouts, and an open back moment, this skater dress is made for sunny flings and girls’ night things.

    Fit & Features

    • Sheer chiffon fabric with lining
    • Sleeveless sweetheart neckline, padded bra cups
    • Tie-back halter straps, smocked back
    • Side cutouts leading to an open lower back
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000146

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Moves Criss-Cross Strap Block Heels

    Make only stylish moves in these sleek strappy block heels! They feature an open square-shaped toe, thin asymmetric toe straps in a criss-cross design, thin adjustable ankle and heel straps with a buckle, and a thin block heel. Pair with an oversized blazer and a mini handbag to wear from the office to happy hour.

    Fit & Features

    • Open square toe
    • Asymmetric criss-cross toe straps
    • Adjustable ankle and heel straps, buckle detail
    • Open back
    • Thin block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4673

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea Salt Vibes Halter Crochet Midi Dress

    Your next vacay is calling, and this crochet midi dress will set the vibes! Embrace the sand and sun in this stylish dress designed with a flattering high neckline and form-hugging fit.

    Fit & Features

    • Crochet knit fabric, stretchy knit lining
    • High halter neckline, spaghetti strap ties
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000028

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Another Day Long Sleeve Sweater Midi Dress

    Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.

    Fit & Features

    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Soft, stretchy sweater rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5305

    Category Name: Vacation Looks

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Chic High-Rise Wrap-Slit Midi Skirt

    Creating chic looks this summer with this high-rise midi skirt is essential for the weekend or casual office days. Crafted from a woven fabric with a stretchy knit lining, you'll adore this skirt all season. This skirt boasts a flattering style with delicate pleating, leading to the wrap-slit front design and a midi-length hem. Complete the look in heeled sandals and a bodysuit.

    Fit & Features

    • Woven fabric, stretchy knit lining
    • High-rise pleated waist
    • Back zipper and hook-eye closure
    • Front wrap-slit design
    • Midi-length
    • Runs true to size

    Style Number/Barcode: 06301-0187

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Style Lace-Up Eyelet Skater Dress

    Show off the sweetest style at your weekend plans in this airy eyelet skater dress! Designed with a lace-up bust and fit-and-flare silhouette, pair with a charm necklace.

    Fit & Features

    • Woven eyelet fabric
    • Sleeveless square neckline, lace trim, lace-up bust design
    • Pleating at the bodice, back zipper closure
    • Thin adjustable tank shoulder straps
    • High waist seam
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3951

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: WHITE

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

  • Cuddly Cute Checkered Faux Fur Bucket Hat

    This cuddly cute checkered faux fur bucket hat is a trendy addition to your winter wardrobe! It features a classic bucket hat design composed of an ultra-soft faux fur material with an on-trend checkered print pattern. The woven lining features an adjustable drawstring. Style with a fringe scarf for a cozy look.

    Fit & Features

    • Classic bucket hat design
    • Short brim
    • Checkered print
    • Faux fur material
    • Woven lining
    • Interior adjustable drawstring

    Style Number/Barcode: 07302-1562

    Category Name: Vacation Looks

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beauty So Bold Floral Mesh Maxi Dress

    Stroll like a bold beauty in this floral mesh maxi dress for any occasion! Its strapless design and curve-hugging fit accentuate your natural beauty, while the flowing maxi hem adds elegant movement.

    Fit & Features

    • Bold floral print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000058

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Country Nights Denim Western Booties

    Go out tonight in these western booties for a country bar or bachelorette! The booties feature a pointed toe, western-inspired stitching, a stacked block heel, and a back zipper closure on an ankle-length shaft. Complete the look in a cowboy hat.

    Fit & Features

    • Pointed toe
    • Western-inspired stitching
    • Stacked block heel
    • Back zipper closure
    • Ankle-length shaft
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07403-1711

    Category Name: Vacation Looks

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glow Up Button-Front Cropped Vest

    Hit the scene in the glow up button-front cropped vest. This ribbed knit piece flaunts a sleeveless V-neckline and a chic button-front. Perfect for adding a touch of glam to any outfit.

    Fit & Features

    • Lurex knit fabric
    • Sleeveless V-neckline
    • Single button-front closure
    • Fitted cropped ribbed hem
    • Runs true to size

    Style Number/Barcode: 06005-2149

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Cue The Comfort Fuzzy Woven Fringe Scarf

    You'll be ready for the cold with this fuzzy woven scarf featuring a thick and warm design to help keep you cozy and fringe details. Complete the look with a trench coat for day or night plans!

    Fit & Features

    • Thick fuzzy woven material
    • No stretch
    • Long design
    • Fringe details

    Style Number/Barcode: 07305-0457

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Vacay V-Neck Floral Maxi Dress

    Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4076

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, L

  • Kick Up A Storm Faux Leather Western Boots

    Kick up a stylish storm in these faux leather western boots! They feature a sleek pointed-toe, inner zipper closure, a block heel, trendy western-inspired stitching, and the perfect under-the-knee length with side pull tabs for easy on-and-off styling. Complete the look with a cowboy hat for a bachelorette or country concert!

    Fit & Features

    • Pointed-toe, block heel
    • Inner zipper closure
    • Western-inspired stitching
    • Under-the-knee shaft length
    • Side pull tabs, easy-on-and-off styling
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0973

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Fantasy Strapless Cutout Maxi Dress

    Easy to wear, impossible to forget! Make your entrance in this floral maxi dress designed with a flirty cutout and form-hugging fit that accentuates your figure.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Strapless neckline
    • Cutout bodice
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000079

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • What A Cutie Knit Pom Beanie

    You'll look like a total cutie in this knit beanie! Featuring a furry pom top, and a fair isle pattern, and is composed of cozy knit material. Complete the look in a puffer vest for cold days!

    Fit & Features

    • Furry pom top
    • Fair isle pattern
    • Knit material
    • Warm and soft design

    Style Number/Barcode: 07302-1515

    Category Name: Vacation Looks

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful View Halter Crochet Crop Top

    Enjoy stylish bliss in this crochet top on your next getaway or weekend outing! The top offers a flattering halter neckline with a spaghetti strap tie and a fitted crop hem. Complete the look with the matching midi skirt.

    Shop Matching Bottoms: Blissful View Crochet Knit Midi Skirt

    Fit & Features

    • Crochet knit fabric, geometric pattern, knit lining
    • Halter neckline with spaghetti strap tie
    • Cropped length
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2005

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S

    Product Badge:
    • Sale
  • Stay Toasty Cable Knit Beanie

    This cable knit beanie has you covered with toasty warmth and style! The cable knit fabric and foldover design make this beanie a stylish addition to any winter look. Complete the look with the matching scarf for a fun winter day! 

    Shop Matching Scarf: Cozy Cutie Cable Knit Fringe Scarf

    Fit & Features

    • Cable knit material
    • Foldover design
    • Soft and comfortable

    Style Number/Barcode: 07302-1523

    Category Name: Vacation Looks

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale