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.

  • Summer Staple Tie-Front Midi Dress

    This trendy tie-front midi dress is a stylish summer staple! It features a sleeveless V-neckline, a tie-front design at the bust with a small keyhole cutout, spaghetti straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Pair with espadrille sandals for happy hour.

    Fit & Features

    • Sleeveless V-neckline
    • Tie-front design, small keyhole cutout
    • Spaghetti straps
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5250

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Beauty Abstract Cutout Maxi Dress

    Embrace your vacation looking like beauty in this abstract print maxi dress destined for sunset dinners and cocktails by the pool! It features a sleeveless square neck, sleek bungee spaghetti straps, a sassy cutout waist with a hoop insert, a slim form-hugging silhouette, and a high front slit on lined smooth knit and stretchy fabric. Complete the look in cute sandals and earrings.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Cutout waist, hoop insert
    • Slim form-hugging silhouette
    • High front slit, maxi-length hem
    • Abstract print, smooth knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5101

    Category Name: Vacation Looks

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Basic Crew Neck Tank Mini Dress

    A sweet basic mini dress for all your styling needs this season! It features a sleeveless crew neckline, a bodycon silhouette, and a mini-length fitted hem on smooth and stretchy knit fabric. Complete the look with trendy sunglasses and sandals for a trip to the farmer's market!

    Fit & Features

    • Sleeveless crew neckline
    • Bodycon silhouette
    • Mini-length fitted hem
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5079

    Category Name: Vacation Looks

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elite Summer Style Marble Print Maxi Dress

    Show off an elite summer style in this eye-catching marble print maxi dress! It features a sleeveless scoop neckline, spaghetti straps, an alluring lower back cutout, a maxi-length hem with a thigh-high side slit to showcase some leg, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features a trendy multi-colored marble print pattern. Complete the look with strappy heels for sunset happy hour. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps, lower back cutout
    • Maxi-length hem, high side slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Slinky knit fabric, short knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5261

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss Jetsetter Halter Tie-Back Print Crop Top

    Whether you're jet-setting to your next adventure, meeting friends for brunch, or creating the perfect vacation look, this dual tie-back printed crop top is essential for looking cute on the go! Shop the matching skirt to complete the look.

    Shop Matching Bottoms: Miss Jetsetter High-Rise Print Mini Skort

    Fit & Features

    • Printed design, cotton fabric, bust knit lining
    • Halter V-neckline
    • Dual tie-back details
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000022

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sergeant Of Style Cargo Pocket Mini Dress

    Elevate your status to sergeant of style in this edgy mini dress perfect for casual plans! Featuring a sleeveless square neckline, adjustable spaghetti straps, a lightly padded bust, an underbust seam, cargo-style flap side pockets, and a short bodycon silhouette. Style with strappy clear strap heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Lightly padded bust, underbust seam
    • Back zipper and hook-eye closure
    • Bodycon silhouette, mini-length hem
    • Twill woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5104

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Perfection Striped Tank Mini Dress

    This adorable striped tank mini dress is the perfect casual style for a subtly elevated look! It features a sleeveless crew neckline, tank shoulder straps, a mini-length subtle curved hem, and a bodycon silhouette that offers a form-hugging fit. The striped ribbed knit fabric has plenty of stretch. Pair with strappy sandals.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Mini-length subtle curved hem
    • Bodycon silhouette
    • Striped print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5102

    Category Name: Vacation Looks

    Price: $19.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ethereal Glamour Butterfly Fringe Rhinestone Headband

    Give off an aura of ethereal glamour with this gorgeous embellished headband! It features a thin flexible metal design with mini rhinestone embellishments and long cascading fringe on each side with rhinestones, dainty chains, and detailed butterfly accents. Style with simple stud earrings.

    Fit & Features

    • Thin flexible metal headband
    • Two rows of mini rhinestone embellishments
    • Three rows of dangling fringe on each side
    • Mini rhinestones, dainty chains, butterfly accents

    Style Number/Barcode: 07006-0404

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevate Everyday V-Neck Tank Crop Top

    Elevate every outfit with this basic tank top perfect for dressing up, down, or layering! It features a sleeveless V-neckline, wide shoulder straps, and a fitted crop hem on stretchy rib knit fabric. Complete the look in a trendy mini skirt and earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Wide shoulder straps
    • Fitted crop hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1637

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Chic Twist-Front Crop Top

    Showcase your artsy side in this abstract chic twist-front crop top! It features a sleeveless V-neck and back design, tank shoulder straps, a twist-front design at the bust, a fitted cropped hem, and an all-over multi-colored swirl print pattern. Style with the matching straight-leg pants for a bold allure.

    Shop Matching Bottoms: Abstract Chic Straight-Leg Pants

    Fit & Features

    • Sleeveless V-neck and back
    • Tank shoulder straps
    • Twist-front design at the bust
    • Fitted cropped hem
    • Multi-colored abstract swirl print
    • Knit slink fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4894

    Category Name: Vacation Looks

    Price: $4.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Chic Straight-Leg Pants

    Showcase your artsy side in these abstract chic straight-leg pants! They feature a high-rise banded waist, a hip-hugging fit, a straight-leg silhouette, and an all-over multi-colored swirl print pattern. Style with the matching crop top for a bold allure. 

    Shop Matching Top: Abstract Chic Twist-Front Crop Top

    Fit & Features

    • High-rise banded waist
    • Hip-hugging fit
    • Straight-leg silhouette
    • Multi-colored abstract swirl print
    • Knit slinky fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2364

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Finders Keepers Tie Dye Mini Dress

    Lucky you to have found this tie-dye mini dress! Perfect for summer fun, this sleeveless dress features a square neckline, spaghetti straps, adjustable side drawstrings let you customize the style, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in strappy sandals for a backyard dinner party!

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Adjustable side drawstrings
    • Bodycon silhouette
    • Mini-length hem
    • Unique tie-dye print
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5224

    Category Name: Vacation Looks

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Eyes Only Slide Sandals

    These comfy-cute slides feature a clear strap topped with a bold heart charm—perfect for pool days, park hangs, or running errands like a style icon.

    Fit & Features

    • Round toe
    • Clear PVC strap with heart cutout
    • Comfortable footbed
    • Platform sole
    • Runs true to size

    Style Number/Barcode: 07404-000005

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: In Stock

    Available Color: CLEAR

    Available Size: 5.5, 6.5, 7, 7.5

    Product Badge:
    • Sale
  • Summer In Tie Dye Cutout Midi Dress

    Spend your summer in this tie-dye midi dress perfect for backyard dinners to sunset cocktails! It features a sleeveless V-neckline, spaghetti straps, a sexy cutout waist, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in trendy doorknocker earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Cutout waist
    • Bodycon silhouette
    • Midi-length hem
    • Tie-dye print, stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5225

    Category Name: Vacation Looks

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meet Your Match Bandage Crop Top

    Meet your match! This bandage crop top is the style you'll be obsessed with all season. It features a sleeveless plunge V-neckline, tank shoulder straps, a square low-cut back, and underbust seam detail. The crop top is designed from a bandage-seamless knit fabric that fits like a glove. Complete the look with the matching bottoms for a Miami vacation or club night!

    Shop Matching Bottoms: Meet Your Match Bandage Midi Skirt

    Fit & Features

    • Sleeveless plunge V-neckline
    • Tank shoulder straps
    • Square low-cut back
    • Underbust seam detail
    • Cropped hem
    • Bandage-seamless knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1723

    Category Name: Vacation Looks

    Price: $3.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meet Your Match Bandage Midi Skirt

    Meet your match! This bandage midi skirt is the style you'll be obsessed with all season. It features a flattering high-rise waist, bodycon silhouette, center-back slit accent, and a midi-length hem. The midi skirt is designed from a bandage-seamless knit fabric that fits like a glove. Complete the look with the matching top for a Miami vacation or club night!

    Shop Matching Top: Meet Your Match Bandage Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Center back slit accent
    • Back zipper and hook-eye closure
    • Midi-length hem
    • Bandage-seamless knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0865

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fierce And Fine Satin Leopard Midi Dress

    Fierce, fine, and looking flawless in this satin leopard midi dress! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust, and a relaxed slim silhouette. Complete the look with a dainty bracelet and strappy heels for a birthday lunch!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust
    • Relaxed slim silhouette
    • Midi-length hem
    • Leopard print, smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5120

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Lover Crochet Maxi Coverup

    All you need is the sunshine and this crochet maxi coverup for the perfect beach-day vibe! Features a sleeveless, crew neck, form-fitting silhouette, and a sexy side slit. Complete the look in a bikini set and sunglasses.

    Fit & Features

    • Sleeveless, crew neck
    • Form-fitting silhouette
    • Side slit
    • Maxi-length hem
    • Diamond crochet knit pattern
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06005-1435

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fashion Reputation Chiffon Tie-Back Crop Top

    You've got a fashion reputation to uphold and this chiffon crop top will keep you in check! It features breezy sheer peasant long sleeves, a V-neckline with non-slip grip lining, a ruched bust, and a wrap-style hem with tie-back closure. Complete the look in high-rise skinny pants for a dinner party!

    Fit & Features

    • Sheer peasant long sleeves
    • V-neckline, non-slip grip lining
    • Ruched bust
    • Wrap-style cropped hem
    • Tie-back closure
    • Chiffon fabric, bust lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2200

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Definite Yes High Slit Maxi Dress

    This sleek high slit maxi dress is a definite yes for leveling up your casual looks! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem with a thigh-high front slit to showcase some leg, and a slim-fit silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy sandals for a lunch date! 

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Maxi-length hem
    • High front slit
    • Slim-fit silhouette
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5194

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Girl Rib Knit Cutout Jumpsuit

    For all the girls going on a getaway this rib knit jumpsuit will keep you flawless on the island or European adventure! The jumpsuit features a sleeveless V-neckline, spaghetti straps, a flirty bust knot tie accent, a cutout waist and back design, and a flattering straight-leg silhouette. Complete the look in PVC mules for a seamless-chic style!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Bust knot tie accent
    • Cutout waist and back
    • Straight-leg silhouette
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2340

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Back To Basics Halter Rib Knit Crop Top

    Take your style back to basics with this sleeveless crop top perfect for pairing with your go-to bottoms! It features a halter neckline, spaghetti strap, an exposed underbust seam, and a fitted hem on stretchy rib knit fabric. Complete the look in distressed denim for a casual day out.

    Fit & Features

    • Sleeveless halter neckline
    • Spaghetti strap
    • Exposed underbust seam
    • Fitted crop hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1599

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Rhythm Halter Sweater Midi Dress

    Shimmy to the island rhythm with a cocktail in hand wearing this sweater midi dress for the cutest vacation look! It features a sleeveless halter neckline with wood bead accents, spaghetti straps that shape the open lace-up back design, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in chic wedges.

    Fit & Features

    • Sleeveless halter neckline, wood bead accents
    • Spaghetti straps, open lace-up back design
    • Bodycon silhouette
    • Miid-length hem
    • Sweater rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1698

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfection Vibes Chiffon Skater Romper

    Look like perfection in this chiffon skater romper for a night of fun vibes! It features adorable sheer puff short sleeves, a scoop neckline with a flirty bust tie front and keyhole, a sheer elasticized waist, and a flowy short-length hem. Complete the look in strappy heels for a celebration!

    Fit & Features

    • Sheer puff short sleeves
    • Scoop neckline, front bust tie and keyhole
    • Sheer elasticized waist
    • Skater silhouette
    • Flowy short-length hem
    • Airy chiffon fabric, partial knit stretchy lining
    • Runs true to size

    Style Number/Barcode: 06403-0316

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance