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.

  • High Rank Camouflage Cargo Shorts

    Show off your high-ranking status as a fashion commander! These camouflage twill shorts feature a flattering high-rise waist, cargo-style flap pockets with pull-tab closures, and a short-length hem on twill woven fabric with a slight stretch. Complete the look in a basic tank top and your favorite white sneakers!

    Fit & Features

    • High-rise waist
    • Cargo-style flap pockets, pull-tab closures
    • Short-length hem
    • Front button and hidden zipper closure
    • Belt loop accents
    • Camouflage print, twill woven fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06303-0232

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Realness Denim Cutout Maxi Dress

    Sweet from the front, spicy from the back. With bold cutout accents, a hoop insert, and ruffled tiered flow, this maxi is bringing the drama in the cutest way possible.

    Fit & Features

    • Denim fabric, sewn-in knit lining
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Cutout bodice design, hoop insert
    • Stretchy smocked back panel, cutout accent, lower zipper and hook-eye closure
    • Ruffled tiered maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000131

    Category Name: Vacation Looks

    Price: $30.97 $68.90

    On Sale: Yes

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S

    Product Badge:
    • Sale
  • Cozy Stroll Colorblock Fringe Blanket Scarf

    Layer on this adorable colorblock fringe blanket scarf for a cozy stroll to grab coffee! Composed of a soft fuzzy woven material with trendy fringe hems and a cute colorblock pattern, this long scarf is a stylish staple for the season. Pair with a trench coat and booties.

    Fit & Features

    • Soft fuzzy woven material
    • Long fringe hems
    • Long design
    • Colorblock pattern

    Style Number/Barcode: 07305-0471

    Category Name: Vacation Looks

    Price: $3.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Trend Long Sleeve Checker Crochet Sweater

    With this crochet sweater to layer over your outfit or swimsuit, your looks will always be on point! The flare cuffs add a touch of femininity, while the open front with tie closure allows for a customizable fit. The cropped hem and checker pattern make this sweater a stylish and versatile addition to your wardrobe. Complete the look with sunnies.

    Fit & Features

    • Sheer crochet fabric
    • Checker pattern
    • Open front with tie closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-1978

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Cute Crochet Sweater Topper

    From days by the beach to summer nights, this crochet sweater topper will keep you cute all season! 

    Fit & Features

    • Sheer crochet fabric
    • Fitted long sleeves with flare cuffs
    • Crew neck
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000025

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Get Spotted Cow Print Faux Fur Scarf

    Get spotted in this cute cow print scarf as you walk downtown! The trendy scarf features an all-over cow print pattern on a super soft faux fur material. Style with the adorable hat.

    Shop Matching Hat: Trendsetting Look Faux Fur Bucket Hat

    Fit & Features

    • Cow print pattern
    • Faux fur material

    Style Number/Barcode: 07305-0465

    Category Name: Vacation Looks

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamiest Summer Smocked Floral Chiffon Midi Dress

    Have the dreamiest summer romance in this floral chiffon midi dress perfect for dates and parties! This dress features a square neckline, adjustable spaghetti straps, and a stretchy smocked bodycon silhouette for a comfortable and flattering fit. The tiered ruffled midi-length hem adds a touch of femininity, while the floral print on chiffon fabric gives the prettiest look. Style this floral dress with earrings and block heels.

    Fit & Features

    • Floral print, chiffon fabric
    • Adjustable spaghetti straps
    • Square neckline
    • Stretchy smocked bodycon silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-2985

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Flirt Floral Mini Tube Dress

    Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.

    Fit & Features

    • Woven chiffon fabric with stretchy knit lining, dainty floral print
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4077

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Cozy Elevated Faux Sherpa Trim Vest

    This faux sherpa trim vest is a cozy elevated staple for the season! It features a lapel collar, an asymmetric zip-front design, a cropped hem, a fitted silhouette, and faux sherpa trims on the ultra-smooth faux suede fabric. Layer over a long-sleeved bodysuit with jeans and ankle booties for a chic fall vibe.

    Fit & Features

    • Sleeveless bodice, lapel collar
    • Asymmetric zip-front design
    • Two front faux pockets
    • Cropped hem, fitted silhouette
    • Faux sherpa trims
    • Faux suede fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06201-0395

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Hot to Handle Halter Knit Mini Dress

    This halter mini dress hugs you with a bodycon fit and a side sash that brings the drama and accentuates your curves. Pair with sandals for brunch by the beach or vacay!

    Fit & Features

    • Texture knit stretchy fabric, stretchy knit lining
    • Halter neckline with hardware trim, spaghetti strap tie
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front wrap sash design
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000115

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S

    Product Badge:
    • Sale
  • In Love Lace-Up Knee High Boots

    Fall in love with these faux suede boots with endless styling possibilities! They feature an almond toe, inner zipper closure, a short block heel, and a knee-high shaft with a trendy lace-up back. Complete the look in a chic trench coat for a dinner and show downtown!

    Fit & Features

    • Almond toe
    • Inner zipper closure
    • Short block heel
    • Knee-high shaft, lace-up back, tie closure
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-0964

    Category Name: Vacation Looks

    Price: $12.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blissful Aura Floral Ruffle Maxi Dress

    Serve a blissful aura in this floral maxi dress while on vacation or for weekend fun! The delicate V-neckline accentuates your figure, while the form-hugging fit flatters your curves with a bold ruffled design.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining
    • V-neckline, spaghetti straps
    • Form-hugging bodice
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000054

    Category Name: Vacation Looks

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutout Crush Hour Midi Dress

    Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!

    Fit & Features

    • Sweater knit stretchy fabric
    • V-neckline with tie bust design
    • Adjustable spaghetti straps
    • Underbust cutout accent
    • Front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000014

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Feeling Cute Long Sleeve Open Back Catsuit

    You'll be feeling cute in this flattering ribbed long sleeve catsuit. Enjoy the luxurious feel of the comfortable, form-fitting fabric as you show off the sultry open back, keep cozy with the fitted long sleeves and crew neckline with back button closures, and the perfect skinny-leg design. Complete the look in a jacket and cozy boots!

    Fit & Features

    • Fitted long sleeves
    • Crew neckline, back button closures
    • Open back
    • Form-hugging
    • Skinny-leg design
    • Rib-knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06502-2397

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Day Dream High-Rise Wrap Mini Skirt

    Look like a tropical day dream in this mini skirt while on vacation! The high-rise elasticized waistband ensures a comfortable fit, while the bodycon silhouette, wrap front design and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching top and pants.

    Shop Matching Top: Tropical Day Dream Tie-Front Crop Top
    Shop Matching Pants: Tropical Day Dream High-Rise Wide Leg Pants

    Fit & Features

    • Tropical print, stretchy knit fabric lined with knit
    • High-rise elasticized waistband
    • Bodycon silhouette
    • Wrap front design
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06501-0978

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Booked Halter Skater Mini Dress

    This breezy mini dress will inspire you to book a vacay somewhere sunny with an ocean view! With a flattering halter neckline and playful ruffled skater silhouette, this dress is perfect for any getaway.

    Fit & Features

    • Airy woven fabric, stretchy knit lining
    • Halter neckline with spaghetti strap ties
    • Stretchy smocked back, zipper and hook-eye closure
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4038

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: SAGE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Meadow Vibes Floral Eyelet Lace Mini Dress

    Give your closet a dreamy meadow vibe with this floral mini dress - an adorable option for brunch and day dates! Featuring puff short sleeves, a sweetheart neck, front bust tie, and side ruched seam to accentuate your curves along the bodycon silhouette. The dress is composed of a ditsy daisy print on eyelet lace fabric with a stretchy knit lining. Complete the look in strappy sandals.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, front bust tie
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Ditsy daisy print
    • Eyelet lace, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4945

    Category Name: Vacation Looks

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Off Your Curves Smooth Knit Midi Skirt

    This smooth knit midi skirt will show off your curves and create an alluring silhouette. It features a high-rise waist, a midi-length hem with a high-cut side slit accent, and a form-hugging fit to flaunt your figure. The ribbed smooth knit fabric includes a full-length knit lining and offers plenty of stretch. Style this mid-length skirt with a corset top and mules for happy hour.

    Fit & Features

    • High-rise elasticized waist
    • Midi-length hem
    • High-cut side slit
    • Curve-hugging fit
    • Ribbed smooth knit fabric, full-length knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0897

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Aura Sleeveless Sweetheart Eyelet Romper

    You'll always charm with your sweet aura in this sleeveless eyelet romper perfect for wedding showers, graduations, or summer fun! Made of eyelet fabric, it's perfect for a sunny day with its short-length hem. Featuring a flattering sweetheart neckline and adjustable spaghetti straps, this romper also has underwire bust support and a fitted bodice to accentuate your figure. Complete the look with wedge sandals.

    Fit & Features

    • Eyelet fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Sweetheart neckline, underwire bust
    • Back zipper and hook-eye closure
    • Front hook and eye fasteners
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 06303-0249

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Perfect Collar Short Sleeve Mini Dress

    There's nothing more perfect for warmer temps than this rib knit mini dress for an effortless athleisure vibe! This bodycon dress features a chic collar and short sleeves making it ideal for sunny days while the subtle side slit adds a flirty look.

    Fit & Features

    • Rib knit stretchy fabric
    • Collar V-neckline
    • Short sleeves
    • Bodycon silhouette
    • Side slit accent
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000127

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK, WHITE

    Available Size: S/M, M/L

  • Another Slay Sweater Knit Maxi Skirt

    Another day, another slay! This sweater maxi skirt features an elasticized high-rise waist, a form-hugging silhouette, and a flirty center back slit along the hem on soft and stretchy rib knit fabric. Style the maxi skirt with a cute mini handbag and mules for a farmer's market!

    Fit & Features

    • Elasticized high-rise waist
    • Form-hugging silhouette
    • Center back slit
    • Maxi-length hem
    • Sweater rib knit fabric
    • Soft and stretchy
    • Runs true to size

    Style Number/Barcode: 06501-0893

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Favorite Staple Striped Cutout Mini Dress

    Slip into this striped mini dress with a flirty cutout and bodycon fit - it'll be your favorite staple all season long!

    Fit & Features

    • Striped pattern, stretchy rib knit fabric
    • Strapless neckline
    • Cutout accent
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000066

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

  • Taking The Plunge Floral Mesh Crop Top

    Take the plunge to flaunt this floral mesh crop top this spring! With adjustable drawstring straps and ruched seams that accentuate your figure, this top will receive many compliments.

    Fit & Features

    • Floral print, mesh fabric, brushed knit lining
    • Plunge neckline
    • Adjustable drawstring shoulder straps
    • Side ruched seams
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000091

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cinched And Chic Faux Leather Trench Coat

    Create a chic cinched silhouette with this sleek faux leather trench coat. Featuring a lapel collar, long sleeves, an off-center zip-front, a belted waist, and a fitted silhouette, this jacket will amp up your winter 'fits. Layer over a sweater dress with knee-high boots.

    Fit & Features

    • Lapel collar, long sleeves
    • Off-center zip-front
    • Single chest pocket flap
    • Belted waist, rectangular buckle
    • Fitted silhouette
    • Faux leather material, sewn-in woven lining
    • Runs true to size

    Style Number/Barcode: 06204-1520

    Category Name: Vacation Looks

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale