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.

Linked Up Dual Chain Link Belt
Link up with this sassy dual-chain link belt featuring an adjustable lobster clasp closure. Complete the look in denim shorts for any casual occasion!

Fit & Features
- Dual chain link belt
- Adjustable lobster clasp closure
Style Number/Barcode: 07301-1112

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Mystic Pearl Press On Nail Kit
Mystify your alluring presence with this press on nail kit including everything you need to achieve a whimsical flair. The exclusive kit offers two sets of pearly press-on nails with a glowing effect for extra shimmer, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look with faux pearl earrings for a date!

Fit & Features
- Press on nail kit
- Two sets of pearly press-on nails, glow effect
- One mini nail file
- One prep pad with easy instructions
- One glue tube
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07307-0184

Category Name: Vacation Looks

Price: $3.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Flirt Floral Mini Dress
Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched detailing, drawstrings at the hem
- Short, form-hugging fit
- Ribbed knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05102-1404

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Paradise Halter Open Back Slit Midi Dress
Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.

Fit & Features
- Slinky knit fabric, smooth stretchy knit lining
- Halter cowl neckline, beaded spaghetti strap tie
- Open back with spaghetti strap tie
- Bodycon silhouette
- Slit accent, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000283

Category Name: Vacation Looks

Price: $45.90

Availability: In Stock

Available Color: RED, BROWN

Available Size: XS, S, M, L
Casual Fave Ribbed Knit Mini Dress
This basic casual ribbed knit mini dress will be a new fave for the season! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a mini-length hem, and a form-hugging silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sandals for a cute everyday vibe.

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Mini-length hem
- Form-hugging bodycon fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5086

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Summer Babe Oversized Square Sunglasses
These trendy oversized shades will have you looking like a total summer babe! The sunglasses feature an oversized square-shaped design, thin arms with sleek metal geometric chain-link accents, rubber nose pads for support, and tinted lenses with ombre shading. Style with a crop top, a mini skirt, and sandals.

Fit & Features
- Oversized square-shaped design
- Thin arms, metal geometric chain-link accents
- Rubber nose pads
- Tinted lenses, ombre shading
- 100% UV protection
Style Number/Barcode: 07008-1024

Category Name: Vacation Looks

Price: $3.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Seaside Vacay Criss Cross Straw Block Heels
From summer parties to seaside vacays, these straw block heels are a cute essential all season! With an almond toe and crisscross straps adorned with a buckle accent, these straw block heels add a touch of style to your summer look. Complete the look with a matching set.

Fit & Features
- 3.5" Block heel
- Almond toe
- Crisscross straps, buckle strap
- Straw material
- Runs true to size
Style Number/Barcode: 07401-4919

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Crossed Over High-Rise Denim Shorts
Designed with the best fit, these high-rise denim shorts are forever flattering! With a form-hugging fit and a cross-over hem that elevates your everyday look.

Fit & Features
- Medium wash denim fabric, slight stretch
- High-rise waist
- Front button and hidden zipper closure, belt loop accents
- Two back pockets
- Form-hugging fit
- Cross-over hem
- Runs true to size
Style Number/Barcode: 06603-0487

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Contemporary Acetate Oval Hoop Earrings
Achieve contemporary style with these oval hoop earrings! Crafted with high-quality acetate, these hoops offer a modern take on a classic design.

Fit & Features
- Acetate design
- Mini hoop trims
- Post-back closure
Earrings are final sale and may not be returned or exchanged
Style Number/Barcode: 07001-000064

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Glow Floppy Straw Hat
Get a stunning glow this summer with this on-trend floppy hat! It features a fitted top, a wide floppy brim, and is composed of a straw-like material with all-over sequin sparkle details and a frayed hem. Complete your beach-ready look with strappy sandals.

Fit & Features
- Fitted top
- Wide floppy brim
- Straw-like material
- Sequin sparkle details
- Frayed hem
Style Number/Barcode: 07302-0301

Category Name: Vacation Looks

Price: $7.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep Me Cozy Slouchy Knit Sweater
The perfect chilly day staple! Cozy up in this cute sweater featuring slouchy dolman sleeves, a boat neckline, and a relaxed crop hem on rib-knit fabric. Pair with casual trouser pants to complete the look!

Fit & Features
- Slouchy dolman sleeves
- Boat neckline
- Relaxed crop hem
- Soft rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1522

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bejeweled Glitter Jelly Sandals
You fancy huh! Radiate glam in these glitter jelly sandals featuring a round toe, bejeweled t-strap, and adjustable buckle closure. Complete the look in a day dress for a birthday lunch.

Fit & Features
- Round toe
- Bejeweled t-strap
- Adjustable buckle closure
- Glitter jelly material
Style Number/Barcode: 07404-0969

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Staple Sheer Button-Up Tunic
This sheer button-up tunic is such a staple for layering over a cute bikini or a lacey bralette! It features long sleeves with button cuffs, a collared neckline, high side slits along a flowy, round hem. Composed of sheer gauze woven fabric with no stretch.

Fit & Features
- Long sleeves, button cuffs
- Collared neckline
- Button-up front closures
- High-side slits
- Flowy round hem
- Sheer gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1649

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunny Style Floral Chiffon Tiered Skater Dress
Show off an adorable style perf for sunny days in this floral chiffon skater dress! The breezy sheer chiffon fabric is detailed with a dainty floral print for the prettiest look and includes a lightweight woven lining for coverage. The short dress features a sleeveless V-neck and back design with tank shoulder straps, a ruched high waist that flows out to a double-tiered skater skirt, and a flirtatious fit-and-flare silhouette. Complete your outfit with espadrille sandals.

Fit & Features
- Dainty floral print
- Sheer chiffon fabric with woven lining, no stretch
- V-neck and back, tank straps
- Ruched high waist, back zipper with hook and eye closure
- Double-tiered skater skirt
- Fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3029

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachy Dreams Denim Lace-Up Espadrille Wedges
Take your beach style to new heights with these denim lace-up espadrille wedges. The closed almond toe offers a stylish touch while the checkered ankle strap and lace-up ties give you a playful look. Style these wedges with a trendy tote bag for a day under the sun!

Fit & Features
- 3.5" Wedge espadrille heel
- Closed almond toe
- Checkered ankle strap, lace-up ties
- Denim material
- Runs true to size
Style Number/Barcode: 07406-0339

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Approved Ruffled Lace Mini Skort
This airy sheer lace mini skort is totally summer approved, featuring a tiered ruffled design with a short overlay and hidden fitted knit shorts. Style with the matching tie-front top for a flirty vibe.

Shop Matching Top: Summer Approved Sheer Lace Tie-Front Top

Fit & Features
- Sheer lace fabric, high stretch
- Mid-rise waist
- Tiered ruffled design
- Mini-length overlay
- Hidden fitted knit shorts
- Runs true to size
Style Number/Barcode: 06503-000087

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Winter Breeze Faux Fur Knit Beanie
Keep warm from that winter breeze in this adorable chunky knit beanie! It features a twisted cable knit pattern, a fold-over design, and an adorable faux fur pom accent. Style with an oversized sweater.

Fit & Features
- Twisted cable knit pattern
- Fold-over design
- Faux fur pom
Style Number/Barcode: 07302-1324

Category Name: Vacation Looks

Price: $4.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pretty Blooms Floral Strapless Jumpsuit
Soft, flowy, and effortlessly pretty—this strapless jumpsuit feels like your fave playlist on repeat. Wide-leg fit keeps it relaxed while the floral moment brings the charm to your vacay or weekend plans!

Fit & Features
- Floral print, soft and smooth knit fabric, moderate stretch
- Strapless neckline
- Fitted bodice
- Flowy wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000038

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Bombshell Asymmetrical Cutout Dress
Create a head-turning moment with a mini dress that impresses with sultry details! The dress features a sleeveless V-neckline with a criss-cross bodice, spaghetti straps, a cutout at the midriff, and a short length with an asymmetrical hem. The dress is composed of a lined crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and a quilted clutch.

Fit & Features
- Sleeveless V-neckline
- Criss-cross bodice, spaghetti straps
- Cutout at midriff
- Short length
- Asymmetrical hem
- Lined crepe fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4605

Category Name: Vacation Looks

Price: $5.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Luxe Faux Nubuck Lace-Up Block Heels
Keep your look so luxe with stylish heels! The heels feature an open back, lace-up straps, a strap over the toe, an open square toe, and a thin block heel. The heels are composed of a faux nubuck material. Complete look with a bodysuit and high waist shorts.

Fit & Features
- Open back
- Lace-up straps
- Strap over the toe
- Open square toe
- Thin block heel
- Faux nubuck material
Style Number/Barcode: 07401-3066

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Untamed Allure Animal Print Cutout Maxi Dress
For the nights you want all eyes on you. This sultry animal print cutout maxi dress hugs every curve and serves bold, untamed allure to keep you as the main focus.

Fit & Features
- Sheer mesh fabric with mini-length brushed knit lining, high stretch
- Animal print
- Sleeveless plunging halter neckline
- Open back and sides, beaded accents, tie-back straps
- Maxi-length hem, high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000278

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Edgy Sole Lug Knee High Boots
Turn the edge in these knee-high boots featuring a round toe, lug platform sole, and side zipper closure, composed of faux leather material. Complete the look in a cool moto jacket.

Fit & Features
- Round toe
- Lug platform sole
- Side zipper closure
- Knee-high shaft length
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0863

Category Name: Vacation Looks

Price: $4.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sea Me Now Rhinestone Starfish Flat Sandals
Straight from under the sea! Let everyone admire you in these rhinestone starfish flat sandals. Featuring a round toe and t-shaped thong strap with a sparkling rhinestone starfish accent, these sandals are a chic addition to any outfit. The adjustable ankle strap ensures a comfortable fit while the flat sole provides all-day comfort. Complete the look with a crossbody purse.

Fit & Features
- Flat sole
- Round toe
- Rhinestone embellished starfish decor
- Adjustable ankle strap, buckle closure
- Runs true to size
Style Number/Barcode: 07404-1226

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cute Impulse Strappy Open Back Crop Top
Be on your best cutely dressed behavior in this head-turning sleeveless crop top featuring a halter V-neckline with bungee spaghetti strap ties that shape the strappy open back, and a sheer fitted pointed crop hem. Complete the look in denim shorts and sandals for the perfect summer style!

Fit & Features
- Sheer knit fabric, bust knit lining, moderate stretch
- Halter V-neckline, bungee spaghetti strap ties
- Strappy open back
- Pointed crop sheer hem
- Runs true to size
Style Number/Barcode: 06001-5333

Category Name: Vacation Looks

Price: $6.97 $19.90

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