Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.

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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.

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: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
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
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
Trendsetter Mid-Rise Belted Twill Skort
Grab a cute top and this mid-rise skort for a trendsetting outfit of the day! This skort is designed to flatter with a belted mid-rise waist and a bodycon design that accentuates your curves along the mini-length hem.

Fit & Features
- Twill woven fabric
- Mid-rise waist, adjustable belt with buckle closure
- Bodycon fit
- Mini-length hem, shorts lining
- Four-pocket styling, belt loop accents
- Front hidden hook-eye and zipper closures
- Runs true to size
Style Number/Barcode: 06303-000018

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: OLIVE

Available Size: XS, S, M, L
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
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
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
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
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
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
Flirty Aura Puff Sleeve Floral Lace Skater Dress
Captivate them with your flirty aura in the cutest floral lace skater dress! The dainty sheer floral lace fabric will give your look a soft feminine vibe and includes a partial woven lining for coverage. The bodice is shaped with a plunging V-neckline with a tie-front detail and sheer short puff sleeves with elasticized hems. The open back adds to the allure and features a tie-back design. The dual high waist seams lead to a fit-and-flare skater silhouette on a short-length hem that was made to twirl. Style this adorable dress with wedge heels for a spring or summer party!

Fit & Features
- Sheer floral lace fabric with partial woven lining, no stretch
- Plunging V-neckline with tie-front
- Short puff sleeves with elasticized hems
- Open back, tie-back, lower back zipper with hook and eye closure
- Dual high waist seams
- Fit-and-flare skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2967

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Ready High Rise Crochet Maxi Skirt
Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades!

Fit & Features
- Crochet fabric, stretchy knit lining
- High-rise elasticized waist
- High front slit
- Flowy maxi-length silhouette
- Runs true to size
Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top
Style Number/Barcode: 06301-0214

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: In Stock

Available Color: NATURAL

Available Size: L
Product Badge:
- Sale
Retro Vibes Belted Flared-Leg Denim Jumpsuit
This fab belted flared-leg denim jumpsuit will give off major retro vibes for the spring and summer seasons! Designed with a cotton-blend denim fabric, this jumpsuit offers plenty of stretch for comfortable wear. The sleeveless bodice is shaped with a collared V-neckline, followed by a partial zip-front design. The high-rise belted waist will create a snatched look, leading to an iconic flared-leg silhouette. Style this denim jumpsuit with platform heels.

Fit & Features
- Cotton-blend denim fabric, plenty of stretch
- Sleeveless collared V-neckline
- Zip-front
- High-rise belted waist
- Front and back pockets
- Form-hugging fit, flared-leg silhouette
- Runs true to size
Style Number/Barcode: 06602-0484

Category Name: Vacation Looks

Price: $21.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunset Muse Floral Satin Maxi Dress
Giving island goddess IRL. This floral satin maxi features a draped cowl neckline, crisscross back, and curve-skimming fit—perfect for destination weddings, summer soirées, or any RSVP that calls for a slay.

Fit & Features
- Floral print, satin fabric
- Cowl neckline
- Spaghetti straps
- Open strappy back tie
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000658

Category Name: Vacation Looks

Price: $49.90

Availability: In Stock

Available Color: GREEN

Available Size: XXS, XS, S, M, L
Cute In Chevron Print Mesh Crop Top
You'll look cute in this chevron print top for festival season or hitting up the country bar! It features a sleeveless square neck, adjustable spaghetti straps, side ruched seams, and a fitted crop hem. Complete the look in the matching pants.

Shop Matching Bottoms: Cute In Chevron Print Mesh Flare Pants

Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Side ruched seams
- Fitted crop hem
- Chevron print
- Mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4709

Category Name: Vacation Looks

Price: $3.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Straight To Business V-Neck Paper Bag Jumpsuit
From business to play, this paper bag jumpsuit isn't messing around when it comes to chic style! It features a sleeveless V-neck, adjustable spaghetti straps, a pleated tie-front belt waist design, hidden side pockets, and a skinny-leg silhouette on smooth woven fabric. Complete the look in this jumpsuit with a ring set and cropped blazer.

Fit & Features
- Sleeveless V-neck, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Paper bag pleated waist, tie-front belt design
- Hidden side pockets
- Skinny-leg silhouette
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-1299

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chase The Sun Lace-Up Espadrille Wedges
Flaunt a sunny day style in these lace-up espadrille wedges perfect for a beach day, backyard bbq, or vacation!

Fit & Features
- 4" wedge heel
- Almond toe, curved band
- Lace-up ankle straps
- Platform wedge heel
- Runs true to size
Style Number/Barcode: 07406-0364

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Forever Timeless Satin A-Line Slip Dress
This satin slip dress will be a forever and timeless staple! The mini dress features a sleeveless V-neck, adjustable spaghetti straps, a flattering A-line silhouette and short hem on smooth non-stretch satin fabric. Complete the look with the matching top and heels for a cocktail reception.

Shop Matching Top: Forever Timeless Satin Collared Top

Fit & Features
- Sleeveless V-neck
- Adjustable spaghetti straps
- A-line silhouette
- Short-length hem
- Smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-2866

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Bliss Floral Corset Skater Dress
Show off your effortless beauty in this adorable floral print skater dress at weekend brunches or day dates! The corset bodice and lace-up back will snatch your waist, while the short skater silhouette gives off a flirty flair.

Fit & Features
- Floral printed woven fabric, woven lining with lace trim, no stretch
- Sleeveless sweetheart neckline, lace trim, tie-front detail, ruched bust, underwire
- Thin adjustable tank straps with lace trim
- Corset bodice, lace trim, pleating, flexible boning
- Lace-up back design, zipper with hook-eye closure
- V-shaped drop waist, short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000007

Category Name: Vacation Looks

Price: $9.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Look Tie-Front Ruffled Romper
This adorable tie-front ruffled romper will create a flirty look for your weekend plans! Designed with a lightweight woven fabric, it features a sleeveless V-neckline with a tie-front design and a keyhole cutout under the bust, spaghetti straps, dual high waist seams, flowy shorts with a mini-length overlay, and a cute fit and flare silhouette. Style with clear heels for brunch.

Fit & Features
- Sleeveless V-neckline, tie-front, keyhole cutout
- Spaghetti straps, back zipper closure
- Dual high waist seams
- Flowy shorts, mini-length overlay
- Fit and flare silhouette
- Woven fabric, knit lining at the bust, minimal stretch
- Style runs large
Style Number/Barcode: 06403-0435

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stunning Always Bodycon Ruffle Mini Dress
You'll always be remembered as stunning in this mini dress, perfect for brunch or casual parties and plans! The flattering scoop neckline with a delicate rose accent adds a touch of romance, while the bodycon fit showcases your curves and is finished with a flirty ruffled hem.

Fit & Features
- Stretchy knit fabric, knit lining
- Scoop neckline with a rose accent
- Spaghetti straps
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000152

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fuzzy Feels Chenille High-Rise Jogger Pajamas
Get cozy lounging in these chenille jogger pajamas! They feature a high-rise elasticized waistband, a skinny jogger-leg silhouette, and ribbed cuffs on ultra-soft and cozy chenille knit fabric. Complete the look in the matching pajama top and robe for a chill night in!

Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top

Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe

Fit & Features
- High-rise elasticized waistband
- Skinny jogger-leg silhouette
- Ribbed cuffs
- Ultra-soft chenille knit fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0940

Category Name: Vacation Looks

Price: $13.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Twice The Love Rib Knit Crop Top
Dive into cozy rib knit love with this midi skirt! Perfect for everyday styling, this midi skirt features a high-rise elasticized waist and curve-flaunting bodycon silhouette and a side slit that shows some skin. Complete the look with the matching skirt.

Shop Matching Skirt: Twice The Love Rib Knit Midi Skirt

Fit & Features
- Scoop neckline, plunging notched front design
- Long fitted sleeves, flared hems
- Cropped, form-hugging fit
- Smaller notched front detail
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1806

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials