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.

Yoga And Tequila Graphic Halter Top
Balance is hot girl behavior. This graphic top says namaste, then time for shots. Stretchy enough for yoga, spicy enough for last-minute plans, this cheeky top features a halter V-neck and fitted, mid-length hem.

Fit & Features
- Knit fabric, moderate stretch
- Sleeveless V-neckline
- Halter strap, partially open back
- Front script that reads, "I do yoga & drink tequila"
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06002-000163

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: In Stock

Available Color: RED

Available Size: S, M, L
Product Badge:
- Sale
Awaken Beauty A-Line Lace Short Dress
Transform into a vision of beauty in this lace short dress at every party! This stunning dress boasts a sleeveless square neckline with a tie, enhancing your feminine charm. The A-line silhouette and short-length hem flatter your figure, while the intricate lace fabric adds a touch of elegance. Complete the look in stiletto mules and a purse!

Fit & Features
- Lace fabric lined with stretchy knit
- Square neckline with tie
- Wide shoulder straps
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5552

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Darling Appeal Sleeveless Ruffled Midi Dress
You'll always give off a darling appeal in this sleeveless midi dress for casual occasions! With a classic square neckline and dual spaghetti straps, this dress is perfect for any occasion. The stretchy smocked bodice ensures a comfortable fit while the A-line silhouette and ruffled midi-length hem add a flattering touch. Complete the look in sandals and a crossbody bag.

Fit & Features
- Woven fabric, no stretch
- Square neckline
- Dual spaghetti straps
- Stretchy smocked bodice
- A-Line ruffled silhouette
- Runs true to size
Style Number/Barcode: 05102-5457

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Case In Point High-Rise Trouser Shorts
Make a polished point in these high-rise trouser shorts with convenient side pockets and a slim-fit silhouette, they're perfect for elevating any OOTD!

Fit & Features
- Woven fabric
- High-rise waist
- Hidden front hook-eye and zipper closure
- Side pockets
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 06403-1113

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spill The Secrets Abstract Print Halter Top
For when your outfit's louder than your group chat. This abstract print mesh halter top is light, effortless, and made for catching stares you weren’t even trying for.

Fit & Features
- Mesh fabric, high stretch
- Abstract print
- Sleeveless plunge V-neckline
- Tie-front detail under the bust, front flyaway design
- Halter spaghetti straps, tie-back design, partially open back
- Mid-length hem, flowy fit
- Runs true to size
Style Number/Barcode: 06001-000162

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: L
Product Badge:
- Sale
Dreaming Of You Floral A-Line Midi Dress
You'll be dreaming of outdoor events and parties to wear this floral midi dress to! It's designed with dainty trim accents along the bodice and a flowy A-line silhouette.

Fit & Features
- Dainty floral print, woven fabric, stretchy knit lining
- Square neckline, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Dainty trim accents in the bodice
- Drop waist seam
- A-line silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4023

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Here For Admiration Corset Lace-Up Eyelet Skater Dress
Be prepared for much admiration when you're in this eyelet skater dress designed with the prettiest corset bodice and lace-up back that turns heads! Perfect for shower celebrations, graduations, and brunch.

Fit & Features
- Eyelet fabric, tulle and woven linings
- Sweetheart neckline, bust tie, underwire bust, spaghetti strap ties
- Lace-up back, side zipper and hook-eye closure
- Corset bodice, flexible boning inserts
- Drop waist seam with ruffle trim
- Skater silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05101-3946

Category Name: Vacation Looks

Price: $54.90

Availability: Out of Stock
Product Badge:
- Ships Free
Tea Time Corset Lace-Up Floral Skater Dress
It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!

Fit & Features
- Floral print, poplin woven lined lace trim fabric
- Square neckline, lace trim, underwire bust, wide shoulder straps
- Corset bodice, flexible boning, lace trim, lace-up back
- Drop waist seam
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3923

Category Name: Vacation Looks

Price: $9.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Crush Striped Crochet Midi Skirt
POV: you just found your new fave beach-to-brunch vibe. This striped crochet midi skirt serves laid-back heat with a form-hugging fit and thigh-high slit made for turning heads from sunrise to sunset.

Shop Matching Top: Summer Crush Striped Crochet Bralette Top

Fit & Features
- Crochet knit fabric
- Striped pattern
- High-rise waist
- Thigh-high side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000027

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Sweetie Gingham Lace-Up Peplum Crop Top
Have yourself the sweetest summer in this gingham peplum top! Featuring playful puff sleeves and a flattering lace-up peplum ruffle, this crop top is perfect for any occasion.

Fit & Features
- Gingham print, cotton woven fabric
- Puff short sleeves
- Sweetheart neckline
- Spaghetti strap tie back design, stretchy smocked panel
- Front lace-up
- Peplum ruffle crop hem
- Runs true to size
Style Number/Barcode: 06003-000029

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Garden At Sunset Strapless Floral Maxi Dress
Perfect for RSVPs or cocktail bars at golden hour! This strapless mesh maxi dress hugs in all the right places with a sultry back cutout and dreamy floral print.

Fit & Features
- Floral print, mesh-lined fabric, high stretch
- Strapless neckline
- Cutout back, lower ruched seam
- Mermaid silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000338

Category Name: Vacation Looks

Price: $21.97 $48.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: S
Product Badge:
- Sale
Can’t Talk, Busy Strutting Block Heel Mules
These mules are giving legs for days. With sleek thong straps, a comfy block heel, and a padded insole, this pair takes you from brunch to rooftop drinks without missing a step.

Fit & Features
- 2" Block heel
- Faux leather material
- Open square-shaped toe
- Thong strappy design
- Open back, on-and-off styling
- Padded insole
- Runs true to size
Style Number/Barcode: 07401-000090

Category Name: Vacation Looks

Price: $28.90

Availability: In Stock

Available Color: NUDE

Available Size: 10
Lowkey Head Turner Open Back Mini Dress
She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.

Fit & Features
- Rib knit fabric, smooth, stretchy knit lining
- Crew neck
- Open back with tie detail
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000159

Category Name: Vacation Looks

Price: $17.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, L
Product Badge:
- Sale
Power Moves Button Woven Vest
Make power moves and take your style to a polished level in this button-up woven vest. Pair with the matching bottoms to complete the look.

Fit & Features
- Woven fabric, sewn-in woven lining
- Button-up front closures
- Stretchy smocked back
- Fitted crop hem
- Runs true to size
Shop The Matching Bottoms: Power Moves High-Rise Trouser Pants
Style Number/Barcode: 06204-2104

Category Name: Vacation Looks

Price: $15.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Mode High-Rise Cotton Shorts
Activate summer mode with these lightweight cotton shorts featuring a high-rise elasticized waist, dual front pockets, and a fitted silhouette. Style with the matching bra top and button-down top for an effortlessly chic look.

Shop Matching Set: Summer Mode Cotton Bra Top, Summer Mode Button-Down Cotton Top

Fit & Features
- Textured cotton fabric, no stretch
- High-rise elasticized waist
- Dual front pockets
- Fitted silhouette
- Shorts in size small have a 9" front rise with a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06303-000030

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: CHARTREUSE

Available Size: S, M, L
Product Badge:
- Part of a Set
No Strings Attached Halter Strappy Midi Dress
Not for the shy girls. With a deep plunge, strappy back, and leg-revealing slit, this one’s here to make jaws drop—casually, of course.

Fit & Features
- Slinky knit lined fabric, moderate stretch
- Plunge halter V-neckline, spaghetti strap tie
- Strappy open back
- Side ruched seams
- Side slit
- Bodycon fit, midi-length hem
- Runs true to size
Style Number/Barcode: 05103-000417

Category Name: Vacation Looks

Price: $36.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S
Edgy Girlie Mid-Rise Studded Denim Skort
Modern and edgy, this mid-rise denim skort brings the cool factor to your concert or going-out look! Let the studded pocket trim add a touch of daring to your outfit, while the bodycon fit flatters along the mini-length.

Fit & Features
- Denim fabric, non-stretch
- Mid-rise waist
- Bodycon fit, mini-length skirt overlay
- Shorts lining
- Studded pocket trim on the front, back pockets
- Front button and hidden zipper closure, belt loop accents
- Runs true to size
Style Number/Barcode: 06603-000029

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sun Chaser Woven Raffia Hoop Earrings
Vacay mode: fully activated. These woven raffia hoop earrings mix chill island vibes with bold hoop energy—perfect for beach brunch or rooftop golden hour.

Fit & Features
- Wide open hoop silhouette
- Woven raffia and metal blend design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000029

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Destiny Disc Coin Hand Chain
This eye-catching hand chain drapes elegantly across your hand, featuring delicate coin disc charms that catch the light with every movement. Perfect for festivals, nights out, or adding a touch of bohemian luxury to any outfit.

Fit & Features
- Disc coins
- Chain
- Lobster clasp closure
Style Number/Barcode: 07003-000018

Category Name: Vacation Looks

Price: $9.90

Availability: Out of Stock
Product Badge:
- Ships Free
Island Muse Tropical Floral Maxi Skirt
Serving island goddess energy with every step. This mesh maxi skirt brings the vacay vibes with tropical floral drama and a form-hugging fit that moves with you from golden hour to after-party. Style with the matching tie-front top for a look that slays.

Shop Matching Top: Island Muse Tropical Floral Tie-Front Top

Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Tropical floral print
- High-rise waist
- Maxi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000055

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sensational Match Ruffle Mini Skort
Make a sensational impression in this ruffled mini skort on vacay or brunch! Pair with the matching top to complete the cute look.

Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

Fit & Features
- Smooth stretchy knit fabric
- Mid-rise waist
- Tiered ruffled design
- Mini-length overlay
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000088

Category Name: Vacation Looks

Price: $26.90

Availability: In Stock

Available Color: BLACK

Available Size: S, M, L
Product Badge:
- Part of a Set
Stylish Day Out Straw Clutch Purse
Whatever your destination, have a stylish day out accessorizing with this straw clutch purse featuring a detachable chain shoulder strap, a front flap, and a spacious interior for your essentials. Complete the look in a summer dress and sandals!

Fit & Features
- Detachable chain shoulder strap
- Front flap
- Spacious interior, two pockets
- Straw material
Style Number/Barcode: 07203-2015

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stand And Deliver High-Rise Pocket Denim Skort
Stand and deliver style in this denim mini skort perfect for casual plans! The high-rise waist and form-hugging fit will accentuate your curves, while the front skirt overlay with flap pockets adds a touch of flair. Plus, the shorts lining with back pockets provide convenience and comfort. Complete the look in a basic tee and boots!

Fit & Features
- Denim fabric, no stretch
- High rise waist
- Front button and hidden zipper closure
- Four-pocket styling
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0402

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glam Life Rhinestone Strappy Faux Leather Sandals
Live that fabulous glam life in these rhinestone strappy sandals perfect for adding that casual glitz to your looks! Made with a patent faux leather material, these sandals have a stylish sheen for that extra flair. The open square-shaped toe is followed by a thin strappy banded design with iridescent mini rhinestone embellishments for the prettiest sparkle. The open back and flat sole offer effortless on-and-off styling. Pair these sandals with a cute handbag.

Fit & Features
- Patent faux leather material
- Open square toe
- Thin strappy banded design
- Iridescent mini rhinestones
- Open back, flat sole
- On-and-off styling
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07404-1152

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials