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.

Looking Like A Daydream Eyelet Lace Dress
Look like a daydream in this adorable eyelet lace mini dress for your next date. Designed with short puff sleeves and a bodycon silhouette with a ruffled hem, you'll bring flirty vibes.

Fit & Features
- Eyelet lace fabric with knit lining, moderate stretch
- Sweetheart neckline, ruched bust
- Short puff sleeves, ruffle trim
- Bodycon silhouette
- Mini-length tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-6059

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Remarkable Allure Long Sleeve Mini Dress
You'll look all kinds of alluring in this long sleeve mini dress in a sultry bodycon fit perfect for dressing up or down.

Fit & Features
- Stretchy knit fabric
- Fitted long sleeves
- Square neckline
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6063

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Zesty Cutie Orange Print Pajama Top
Zesty and cute, this orange print pajama top makes sleeping or lounging juicy sweet! Pair with the matching pajama shorts to complete the look.

Fit & Features
- Orange print, stretchy rib knit fabric
- Short sleeves
- Crew neckline
- Fitted crop hem
- Runs true to size
Shop The Matching Pajama Shorts: Zesty Cutie Orange Print Pajama Shorts
Style Number/Barcode: 07103-000014

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Darling Woven Drop-Waist Skater Dress
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace.

Fit & Features
- Woven fabric with lace trim woven lining
- Sweetheart neckline, ruched bust, adjustable tie-front
- Tank straps, lace-up back design
- Back zipper and hook-eye closure
- Asymmetric drop-waist, pleated side panels
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3806

Category Name: Vacation Looks

Price: $9.97 $64.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Charming Moves Woven Bow Sandals
Make charming moves in these casual-chic woven sandals with the cutest bow strap design.

Fit & Features
- Woven material
- Open square toe
- Toe strap with bow accent
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1270

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stunning Love Floral Lace Babydoll Mini Dress
The most stunning floral mini dress to add to your closet! Featuring a cutout accent and tie back, this babydoll silhouette adds a flirty touch perfect for shower celebrations, graduation, or brunch!

Fit & Features
- Floral print, lace fabric with lining
- Sweetheart neckline, cutout bust, padded bra cups
- Adjustable spaghetti straps
- Tie back
- Babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4063

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Out In The Town Lace-Up Skater Dress
Playful and daring, this skater dress showcases your best self with a lace-up back design and flowy short-length hem.

Fit & Features
- Eyelet fabric
- Scoop neckline
- Adjustable spaghetti straps
- Lace-up back design
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-000013

Category Name: Vacation Looks

Price: $33.90

Availability: Out of Stock
Product Badge:
- Ships Free
Love For Bows Strapless Ponte Crop Top
What's not to love about this adorable bow crop top? It boasts a sleek strapless neckline with front bows and a flirty cutout.

Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless neckline
- Front bows, cutout design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000122

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Bit Of Sweetness Off-Shoulder Crop Top
This fun and flirty off-shoulder crop top adds a bit of sweetness to your favorite bottoms!

Fit & Features
- Smooth, stretchy knit fabric
- Off-shoulder neckline
- Tie-back design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000044

Category Name: Vacation Looks

Price: $11.97 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Kissed By Blooms Corset Skater Floral Dress
Blossom so cute in this skater floral dress boasting a corset bodice that flaunts your femme figure and a trendy lace-up back for added allure!

Fit & Features
- Floral print, woven fabric, tulle and woven linings
- Sweetheart neckline
- Adjustable spaghetti straps, side zipper and hook-eye closure
- Lace-up smocked stretchy back
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3769

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Much Personality Strappy Block Heels
Give your outfits some cuteness in these strappy block heels, perfect for pairing with your favorite bottoms or dresses!

Fit & Features
- 3" Round block heel
- Square toe
- Strappy design
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000087

Category Name: Vacation Looks

Price: $28.90

Availability: In Stock

Available Color: RED, WHITE, YELLOW, BLACK

Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Check Me Out Mid-Rise Gingham Shorts
With these mid-rise gingham shorts, you'll be checking yourself out in every mirror you pass!

Fit & Features
- Gingham print, woven fabric
- Mid-rise waist
- Ruffled trim hem
- Runs true to size
Style Number/Barcode: 06303-000025

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: In Stock

Available Color: BLK/WHT

Available Size: S, M, L
Product Badge:
- Sale
Pretty Escape Lace-Up Espadrille Wedges
Strut looks pretty in these lace-up espadrille wedges while on vacation or weekend fun!

Fit & Features
- Wedge heel
- Square toe, crisscross straps
- Lace-up ankle straps
- Platform sole
- Espadrille material
- Runs true to size
Style Number/Barcode: 07406-000002

Category Name: Vacation Looks

Price: $30.90

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Beauty Floral A-Line Chiffon Maxi Dress
You'll take every soiree by storm when you've got this floral chiffon maxi dress! The A-line silhouette flatters every figure while the flowy maxi-length hem adds effortless style.

Fit & Features
- Floral print, chiffon lined fabric
- Square neckline, tie bust
- Adjustable spaghetti straps
- A-line silhouette
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3970

Category Name: Vacation Looks

Price: $9.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Fly Abstract Slit Crop Top
Bring the heat in this abstract slit crop top! Featuring a front slit with hoop insert and an eye-catching abstract print, this top will make you stand out in any crowd.

Fit & Features
- Abstract print, knit fabric
- Strapless neckline
- Front hoop insert and slit
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000114

Category Name: Vacation Looks

Price: $26.90

Availability: In Stock

Available Color: MULTI

Available Size: S, M, L
Strolls In The Sand Halter Bodycon Mini Dress
Stroll the beach in this halter mini dress while on vacation or enjoying the warm weather! The dress is designed in a unique texture knit that hugs your curves in a bodycon silhouette.

Fit & Features
- Texture knit fabric, stretchy knit lining
- Halter V-neckline, button closures
- O-ring metal insert
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6080

Category Name: Vacation Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
New Babe Strapless Slit Abstract Crop Top
Elevate your babe status in something new! This strapless abstract crop top is designed to flaunt your figure and style with a trendy slit and asymmetrical hem.

Fit & Features
- Abstract print, knit fabric
- Strapless neckline
- Side slit with tie and hoop insert
- Asymmetrical crop hem
- Runs true to size
Style Number/Barcode: 06001-000115

Category Name: Vacation Looks

Price: $26.90

Availability: In Stock

Available Color: MULTI

Available Size: S, M, L
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
All The Vibes Leopard Lace Long Tunic
This leopard lace long flowy tunic will bring all the vibes to your festival 'fit. Designed with a sleeveless bralette top with a leopard print, the long ruffled flyaway design is perf for pairing over denim shorts.

Fit & Features
- Sheer lace fabric
- Sleeveless bralette top, sweetheart neckline, lace trim, leopard print, underwire
- Adjustable spaghetti straps
- Open back, back strap with hook-eye closures, lower back cutout
- Long flyaway design, ruffled trim
- Flowy fit
- Runs true to size
Style Number/Barcode: 06003-000006

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Iconic Street Style Mid-Rise Cargo Denim Skort
Everyone will be eyeing you in this mid-rise denim skort on the street or at a concert! The faux wrap design adds a touch of urban flair, while the form-hugging fit flatters your figure.

Fit & Features
- Denim fabric
- Mid-rise waist, front button closure
- Faux wrap front
- Side cargo pocket
- Form-hugging fit, mini-length hem
- Runs true to size
Style Number/Barcode: 06603-0509

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: BLACK

Available Size: S, M, L, XL
Cute Thing Tie-Back Eyelet Skater Dress
Dressing cute is easy with this eyelet skater dress, perfect for graduates, birthdays, and any occasion that calls for all eyes on you!

Fit & Features
- Eyelet woven fabric, woven lining
- V-neckline
- Adjustable spaghetti straps
- Tie-back design
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-4021

Category Name: Vacation Looks

Price: $9.97 $49.90

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
Love Is In The Details Lace Lace-Up Skater Dress
Fall in love with the pretty details on this lace skater dress from the ruffled shoulder straps to the lace-up back design - this dress is a beauty!

Fit & Features
- Lace lined fabric
- Ruffled shoulder straps
- Sweetheart neckline
- Lace-up back
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-4010

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Heartbreaker Status Rhinestone Sunglasses
Big flirt energy! These rhinestone-trimmed heart frames are here to romanticize your hot girl errands, soft launch your situationship, or just block out bad vibes in style.

Fit & Features
- Metal heart-shaped frame
- Glam rhinestone trim
- Gradient lenses
- Nose-pads
Style Number/Barcode: 07008-000050

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

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