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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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.

Carefree Energy Halter Bodycon Mini Dress
Be a cute sight in this halter mini dress boasting a flattering bodycon fit that perfectly flaunts your curves on vacay or a chic staycation!

Fit & Features
- Texture knit stretchy fabric
- Halter neckline, spaghetti strap ties
- Knotted bust accent
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2302

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Too Cute to Pleat Strapless Romper
Low effort, high impact. This strapless lace romper accentuates the waist and flares with pleated drama—aka, your new going-out obsession.

Fit & Features
- Smooth knit fabric, moderate stretch
- Strapless neckline
- Pleated mini-length hem
- Shorts lining with mesh lace trim
- Runs true to size
Style Number/Barcode: 06503-000096

Category Name: Vacation Looks

Price: $44.90

Availability: In Stock

Available Color: BLACK

Available Size: S, M, L
A Dose Of Attitude Lace-Up Flare Pants
Serve major attitude in these faux suede pants with trending lace-ups and a flared hem perfect for country bars or festivals!

Fit & Features
- Faux suede fabric
- High-rise waist
- Dual front lace-ups
- Hip-hugging fit
- Flare hem
- Runs true to size
Style Number/Barcode: 06502-2577

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
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: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Crowd Hoop Drop Earrings
These earrings will make any outfit stand out! They feature linked hoops in a drop design for the perfect statement. Complete the look in a cute matching set for upcoming plans!

Fit & Features
- Linked hoops
- Drop design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2020

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Perfect View Smocked Cutout Skater Dress
You'll be the prettiest and perfect view for all to see you in this smocked cutout skater dress with breezy long sleeves and a flattering silhouette.

Fit & Features
- Chiffon lined fabric, stretchy knit lining
- Sheer peasant long sleeves
- Sweetheart neckline
- Stretchy smocked bodice with adjustable drawstrings
- Cutout accent
- Stretchy smocked back panel
- Skater silhouette, drop waist seam, short-length hem
- Runs true to size
Style Number/Barcode: 05101-3991

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mermaid Era Dainty Charm Necklace Set
Feels like sunshine, salt air, and summer in every layer. This charm necklace set is giving major sea siren vibes with delicate chains and dreamy shell, sea star, faux pearl, and bead details.

Fit & Features
- Two-pack necklace set
- Layered design
- Dainty chains
- Mixed charms with shell, sea star, faux pearl, and bead accents
- Back lobster clasp closure with adjustable extender
Style Number/Barcode: 07002-000018

Category Name: Vacation Looks

Price: $5.96 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Caught Your Eye Strapless Lace-Up Skater Dress
Catch every eye in this eyelet skater dress with a flirty lace-up bust and a flowy mini-length hem perfect for twirling at parties!

Fit & Features
- Eyelet cotton fabric with woven cotton lining
- Strapless neckline, lace-up bust, padded bra cups
- Skater silhouette
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4009

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feels Like Spring Braided Slingback Sandals
Step into fresh spring style in these braided flat sandals with a trendy closed pointed toe and mini block heel that elevates every outfit!

Fit & Features
- Mini block heel
- Closed braided pointed-toe
- Slingback adjustable strap with buckle closure
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-5316

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Darling Babe Striped Drop Waist Skater Dress
So darling, this striped woven skater dress is effortless perfection. The sleeveless square neckline is accented with a mini bow detail, and the drop waist design leads to a pleated fit-and-flare silhouette.

Fit & Features
- Striped woven fabric
- Sleeveless square neckline, eyelet trim, mini bow detail
- Tank shoulder straps
- Square back, zipper closure
- V-shaped drop waist
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000145

Category Name: Vacation Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tag Along Strappy Buckle Sandals
Whatever your summer plans are, these strappy buckle sandals are perfect for tagging along on any adventure!

Fit & Features
- Round toe
- Dual buckle straps
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-000007

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: In Stock

Available Color: WHITE, BLACK

Available Size: 6, 7, 8
Product Badge:
- Sale
Caught My Attention Floral Lace Bustier
This floral bustier will attract all the attention with its flirty lace trim and flattering silhouette that snatches effortlessly!

Fit & Features
- Floral print, lace trim, woven-lined fabric
- Sweetheart neckline, underwire bust
- Adjustable straps
- Back zipper and hook-eye closure
- Flexible boning, lace trim
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-2771

Category Name: Vacation Looks

Price: $7.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Fave Floral Ruffled Skater Dress
This adorable ditsy floral skater dress will be your new flirty fave to style up all season! You'll love the tiered ruffled design and flowy fit-and-flare silhouette.

Fit & Features
- Woven fabric
- Ditsy floral print
- Strapless straight neckline
- Smocked bodice
- Tiered ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-6052

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortless Eyelet Bubble Hem Mini Dress
You'll look effortlessly pretty in this floral eyelet mini dress featuring a strapless smocked bodice and adorable A-line silhouette with a bubble hem.

Fit & Features
- Floral eyelet woven fabric
- Strapless straight neckline, ruffled trim
- Stretchy smocked bodice, high waist
- Mini-length A-line silhouette
- Bubble hem
- Runs true to size
Style Number/Barcode: 05101-4152

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Set Up Geometric Bandeau Halter Crop Top
Super cute and perfect for getaways or weekend plans, this bandeau crop top is stylish and comfortable for anything on your calendar! It feature a flattering halter neckline with a spaghetti strap tie, an O-ring bust, a cropped hem, and a trendy geometric print on woven fabric. Complete the look with the matching pants.

Shop The Matching Pants: All Set Up High Rise Geometric Palazzo Pants

Fit & Features
- Geometric print, woven fabric, no stretch
- Halter neckline with spaghetti strap tie
- O-Ring bust
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2551

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Day Cuteness Floral Corset Skater Dress
For sunshine dressing, this cute floral skater dress is just the ticket! Designed with a figure-snatching corset bodice and flared short-length hem, this dress is a stylish option for shower celebrations or tea parties.

Fit & Features
- Floral print, cotton-blend woven fabric, smooth knit stretching lining
- Square neckline, bust tie, wide shoulder straps
- Corset bodice, back zipper hook-eye closure
- Drop waist seam, pleated accents
- Skater silhouette
- Flared short-length hem
- Runs true to size
Style Number/Barcode: 05101-3886

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sharp Edge Sunglasses
Future so bright, you need shades this sleek. These geo shaped sunglasses bring instant cool-girl edge to any fit, from brunch ‘fits to poolside lounging.

Fit & Features
- Geo shaped design
- Sleek structured frame
- Tinted 100% UV protective lenses
Style Number/Barcode: 07008-000088

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK

Available Size: NS
Product Badge:
- Sale
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
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
Tied Up In Vibes Crochet Sweater
Cute from the front—but that back? Straight-up stunning. With open-tie drama and airy crochet texture, this sweater is here to steal stares and soak up sunsets.

Fit & Features
- Sheer crochet fabric
- Crew neck
- Flare long sleeves
- Open tie-back design
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06005-000076

Category Name: Vacation Looks

Price: $6.97 $36.90

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
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
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: $9.97 $49.90

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