Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.

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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.

Such A Flirt Sweetheart Lace Trim Skater Dress
This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.

Fit & Features
- Sheer chiffon woven fabric with stretchy knit lining
- Lace trim sweetheart neckline with bow detail, bust underwire
- Adjustable lace trim shoulder straps
- Partially smocked back with zipper and hook-eye closure
- Lace trim bodice, drop waist seam
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3461

Category Name: Vacation Looks

Price: $22.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Desert Daze Straw Cowboy Hat
This straw cowboy hat is giving rodeo queen meets boho babe—lightweight, breezy, and made for your next sun-soaked photo dump.

Fit & Features
- Straw material
- Woven design
- Structured top
- Wide curved brim
- Thin twisted band, tie-back design
Style Number/Barcode: 07302-000070

Category Name: Vacation Looks

Price: $24.90

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Like That Floral Lace Mini Dress
Giving soft girl glam with a flirty twist—this floral lace strapless mini dress brings all the charm. Perfect for brunch, birthdays, or shower celebrations!

Fit & Features
- Floral print lace fabric lined with stretch knit
- Strapless neckline
- Ruched fitted bodice
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000270

Category Name: Vacation Looks

Price: $46.90

Availability: Out of Stock
Product Badge:
- Ships Free
Read All About It Newspaper Bodycon Mini Dress
Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.

Fit & Features
- Newspaper print, knit fabric with stretchy lining
- Adjustable spaghetti straps
- Sweetheart neckline with lace trim
- Back zipper and hook-eye closure
- Built-in padded underwire bust
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5578

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Walk Tall Clear Strap Platform Block Heels
Legs for days and an attitude to match. These clear strap platform mules bring sky-high vibes with a chunky block heel that’s lightweight but never low-key.

Fit & Features
- 5" Thick block heel
- Platform sole, lightweight wood material
- Open square-shaped toe
- Dual clear PVC straps
- Open back, on-and-off styling
- Faux leather cushioned insole
- Runs true to size
Style Number/Barcode: 07401-000260

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: CLEAR

Available Size: 5.5, 6, 7, 7.5, 8, 8.5, 9, 10
So Loved Tube Bodycon Midi Dress
Love at first wear...this tube midi dress elevates your everyday look with curve-accentuating side ruched seams, a bodycon fit, and a side slit for movement.

Fit & Features
- Stretchy rib knit fabric, knit lining
- Strapless tube neckline
- Side ruched seams
- Bodycon silhouette
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000192

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: IVORY

Available Size: XS, S, M, L, XL
Smooth Talker Lace Bow Pleated Ponte Mini Dress
Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.

Fit & Features
- Smooth pointe knit fabric, minimal stretch
- Lace bow trim square neckline
- Spaghetti straps
- Fitted silhouette
- Pleated flare mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3661

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend Vibes Tie-Front Crop Top
This breezy woven crop top will give off those effortless weekend vibes with its flowy short sleeves and tie-front design. Style with the matching wide-leg palazzo pants for a chic look.

Shop Matching Bottoms: Weekend Vibes Wide-Leg Palazzo Pants

Fit & Features
- Woven fabric
- Plunging V-neckline
- Tie-front design
- Short flowy sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-000007

Category Name: Vacation Looks

Price: $19.90

Availability: Out of Stock
Product Badge:
- Ships Free
Love Of Mine Four Piece Bracelet Set
Perfect for stacking or styling alone, this four piece bracelet set will add a chic finishing touch to any look. This versatile bracelet set features an array of complementary styles, some adorned with dazzling rhinestones and elegant faux pearls.

Fit & Features
- Four-piece bracelet set
- One faux pearl bracelet, stretchy fit
- One twisted chain bracelet, lobster clasp closure
- One rhinestone embellished bracelet, toggle closure
- One chain coin charm bracelet, lobster clasp closure
Style Number/Barcode: 07003-000035

Category Name: Vacation Looks

Price: $12.90

Availability: Out of Stock
Product Badge:
- Ships Free
Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress
Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.

Fit & Features
- Floral tie-dye print, smooth knit fabric, moderate stretch
- Strapless neckline
- Lace-up back design
- Form-hugging fit
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3277

Category Name: Vacation Looks

Price: $22.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
You've Got Flare Halter Cutout Wide Leg Jumpsuit
Featuring a flattering halter neckline and playful cutout details, this jumpsuit combines trendiness with a touch of boldness. The wide-leg silhouette and ruffled accents create a flowy look that moves with you.

Fit & Features
- Woven fabric
- Halter plunge neckline, spaghetti strap tie
- Cutout bodice with drawstring tie
- Ruffled wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-000004

Category Name: Vacation Looks

Price: $54.90

Availability: In Stock

Available Color: OLIVE

Available Size: XS, S, M, L
Effortless Chic Mid-Rise Ruffled Shorts
Effortless for vacay or weekend fun, these chic shorts are designed with a smocked drawstring high-rise waist and a ruffled hem!

Fit & Features
- Cotton woven fabric
- Flowy short sleeves
- V-neckline
- Tie-front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06303-000008

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK, LIGHT, BLUE, RED, OFF, WHITE

Available Size: S, M, L, XS
Product Badge:
- Sale
Adorable Basic Scoop Neck Seamless Crop Top
You'll always feel adorable in this basic crop top perfect for layering or styling on its own! The top is crafted from a seamless knit fabric offering plenty of stretch and comfort. It features a flattering scoop neckline, shoulder straps, and a fitted crop hem. Complete the look in denim shorts.

Fit & Features
- Seamless knit fabric, moderate stretch
- Scoop neckline
- Shoulder straps
- Fitted crop length
- Runs true to size
Style Number/Barcode: 07109-0408

Category Name: Vacation Looks

Price: $14.90

Availability: Out of Stock
Product Badge:
- Ships Free
Breezy Babe High-Rise Slit Maxi Skirt
From farmer's market to the beach, this flowy maxi skirt is ready to create stylish looks for any adventure! With a flattering high-rise waist, a flirty front slit, and a tiered silhouette, this skirt is essential for spring to summer.

Fit & Features
- Chambray woven fabric
- High-rise waist
- Front slit
- Tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-0208

Category Name: Vacation Looks

Price: $34.90

Availability: Out of Stock
Product Badge:
- Ships Free
All Day Vibe Mid-Rise Denim Capri Pants
Elevate your casual style in these denim capri pants, perfect for any adventure! The flattering mid-rise waist sits perfectly on your hips, while the form-hugging fit showcases your silhouette with front seam detailing that creates a leg-lengthening effect.

Fit & Features
- Dark wash denim fabric
- Mid-rise waist
- Front seam detailing, form-hugging fit
- Capri-length hem
- Front button closure, belt loop accents
- Back pockets
- Runs true to size
Style Number/Barcode: 06602-0563

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: In Stock

Available Color: DARK, DENIM

Available Size: S, M, L
Product Badge:
- Sale
Denim Diva Square Toe Block Heels
Fall head over heels for these denim block heels! Strut like a diva in these shoes featuring a square toe, a wide band, a block heel, and a luxe fit cushioned faux leather insole for comfort. Complete the look with a trendy handbag for any occasion!

Fit & Features
- 3" Block Heel
- Square toe
- Wide band
- Luxe fit cushioned faux leather insole
- Denim material
- Runs true to size
Style Number/Barcode: 07401-4885

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Buckle Up Baby Pleated Skort
Serving schoolgirl but make it fashionable. With sharp pleats and a bold belt moment, this skort is your go-to for flirty fits with a little edge.

Fit & Features
- Denim fabric, stretchy knit shorts lining
- High-rise belted waist, side zipper and hook-eye closure
- Pleated mini-length skirt overlay
- Runs true to size
Style Number/Barcode: 06603-000059

Category Name: Vacation Looks

Price: $42.90

Availability: In Stock

Available Color: BEIGE

Available Size: XS, S, M, L
Unique Addition Strapless Cut Out Tube Crop Top
A chic strapless tube top makes a unique addition to your fashion lineup! The cutest date or night-out top features a strapless neckline, a trendy side cutout with an adjustable drawstring, and an asymmetrical cut cropped hem. Complete the look in a cute mini skirt and your favorite heels.

Fit & Features
- Soft knit stretchy fabric
- Strapless neckline
- Side cutout, adjustable drawstring
- Asymmetrical cut cropped length
- Runs true to size
Style Number/Barcode: 06001-5377

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Clueless Vibes Denim Belted Mini Skirt
Serving throwback prep with a spicy upgrade. This denim houndstooth mini skirt brings the drama with a statement belt and a mini silhouette made to steal glances.

Fit & Features
- Houndstooth pattern, denim cotton-blend fabric, no stretch
- Mid-rise belted waist
- Bodycon mini-length silhouette
- Front button and hidden zipper closure
- Back pockets, belt loop accents
- Runs true to size
Style Number/Barcode: 06601-000007

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: DENIM

Available Size: XS, S, M, L
Weekend Vibes Wide-Leg Palazzo Pants
These breezy woven palazzo pants will give off those effortless weekend vibes with their relaxed, wide-leg silhouette. Style with the matching tie-front crop top for a chic look.

Shop Matching Top: Weekend Vibes Tie-Front Crop Top

Fit & Features
- Woven fabric
- High-rise waist
- Dual front pockets
- Pleating
- Flowy wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-000004

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: ORANGE

Available Size: S, L
Product Badge:
- Part of a Set
Everyday Beauty Sleeveless A-Line Mini Dress
This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.

Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5631

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Too Cute To Catch Belted Ruffle Skort
Catch her if you can—she’s booked, busy, and best dressed. This ruffled mini skort brings all the bounce for brunch, day parties, and spontaneous Insta moments.

Fit & Features
- Woven fabric
- High-rise belted waist, belt loop accents
- Hidden side zipper and hook-eye closure
- Ruffled skirt overlay, shorts lining
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000025

Category Name: Vacation Looks

Price: $44.90

Availability: Out of Stock
Product Badge:
- Ships Free
Sweetly Coy V-Neck Slit Lace Crop Top
Enhance your everyday style in this lace crop top featuring a V-neckline with a twist accent, spaghetti straps, and a center slit design. The lace-lined fabric offers stretch and a romantic look.

Fit & Features
- Lace lined fabric, minimal stretch
- V-neckline with twist
- Spaghetti straps
- Center slit
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06001-5431

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Way She Moves Striped Midi Skirt
This striped midi skirt has entered the girl's vacay chat! Boasting a sexy bodycon silhouette and mid-rise waist, you'll be the hit of the trip. Pair with the matching top to complete the look!

Shop Matching Top: Way She Moves Striped Bra Top

Fit & Features
- Striped print, scalloped trim, stretchy knit fabric
- Mid-rise waist
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06401-0743

Category Name: Vacation Looks

Price: $46.90

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials