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.

Cozy Vibes Faux Sherpa Shacket
Layer on all the cozy vibes with this trendy faux sherpa shacket! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, side pockets, and a relaxed oversized fit for that ultra-comfy feel. The soft faux sherpa fabric includes a cotton-blend lining. Pair this adorable shacket over a basic bodysuit with faux leather leggings and combat boots!

Fit & Features
- Collared neckline
- Long sleeves, single button detail
- Complete button-down front
- Dual buttoned chest pockets
- Dual lined side pockets
- Faux sherpa fabric, cotton-blend lining, minimal stretch
- Relaxed oversized fit
Style Number/Barcode: 06201-0408

Category Name: Vacation Looks

Price: $9.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dainty Cubic Zirconia Evil Eye Charm Necklace
Radiate and sparkle with positive energy in this delicate evil eye charm necklace! It features a dainty chain with an evil eye charm embellished with mini cubic zirconia stones and beaded detailing for a pretty vibe. Style with hoop earrings and strappy sandals.

Fit & Features
- Dainty chain
- Evil eye charm
- Mini cubic zirconia stones, beading
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1777

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Simplicity Open-Circle Charm Necklace
Effortlessly elevate your looks with this sleek charm necklace, a chic simple accessory for every day. It features a dainty chain with a delicate open circle charm at the center. Style with hoop earrings.

Fit & Features
- Dainty chain-link design
- Center open-circle charm
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1807

Category Name: Vacation Looks

Price: $3.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Drama Meets Paradise Floral Maxi Dress
Giving goddess energy with every step you take. This mesh maxi dress clings in all the right places with a daring cowl neckline and a strappy open back made to be seen.

Fit & Features
- Floral print, mesh fabric, soft stretchy knit lining
- Plunging cowl neckline
- Strappy open back with hoop insert
- Form-hugging fit
- Flowy maxi hem and front slit
- Runs true to size
Style Number/Barcode: 05101-000352

Category Name: Vacation Looks

Price: $46.90

Availability: In Stock

Available Color: BROWN

Available Size: S, M, L
Second Look Turtleneck Open Back Sweater
This cozy crop sweater will make everyone do a double-take! Featuring slouchy long sleeves with ribbed cuffs, a turtle neckline, and a cute surplice open back design on a relaxed silhouette on ultra-soft knit fabric. Complete the look in a mini skirt and your favorite boots for a coffee date or pumpkin patch.

Fit & Features
- Long sleeves, ribbed cuffs
- Turtle neckline
- Surplice open back
- Relaxed silhouette, cropped hem
- Ultra-soft rib knit sweater fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1744

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty In Floral Sweetheart Bodycon Mini Dress
Step out in this flirty floral mini dress for Valentine's Day, dates, and parties! Showcasing a ditsy floral print on soft brushed knit fabric, this dress features a bust tie keyhole, side ruching, and a bodycon fit, to accentuate your figure. Complete the look with a mini purse and heels.

Fit & Features
- Ditsy floral print, brushed knit fabric with stretch
- Spaghetti straps
- Bust tie keyhole
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5523

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Bliss Tie-Back Slit Maxi Dress
Ideal for making a statement at any occasion, this artsy print maxi dress combines chic with effortless style. Featuring a flattering A-line silhouette and a stylish front slit, this dress offers a breezy look that turns heads with a tie-back design.

Fit & Features
- Artsy print, woven fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Tie-back design
- A-line silhouette
- Front slit, flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6039

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
High Rank Camouflage Cargo Shorts
Show off your high-ranking status as a fashion commander! These camouflage twill shorts feature a flattering high-rise waist, cargo-style flap pockets with pull-tab closures, and a short-length hem on twill woven fabric with a slight stretch. Complete the look in a basic tank top and your favorite white sneakers!

Fit & Features
- High-rise waist
- Cargo-style flap pockets, pull-tab closures
- Short-length hem
- Front button and hidden zipper closure
- Belt loop accents
- Camouflage print, twill woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06303-0232

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cozy Stroll Colorblock Fringe Blanket Scarf
Layer on this adorable colorblock fringe blanket scarf for a cozy stroll to grab coffee! Composed of a soft fuzzy woven material with trendy fringe hems and a cute colorblock pattern, this long scarf is a stylish staple for the season. Pair with a trench coat and booties.

Fit & Features
- Soft fuzzy woven material
- Long fringe hems
- Long design
- Colorblock pattern
Style Number/Barcode: 07305-0471

Category Name: Vacation Looks

Price: $3.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Total Trend Long Sleeve Checker Crochet Sweater
With this crochet sweater to layer over your outfit or swimsuit, your looks will always be on point! The flare cuffs add a touch of femininity, while the open front with tie closure allows for a customizable fit. The cropped hem and checker pattern make this sweater a stylish and versatile addition to your wardrobe. Complete the look with sunnies.

Fit & Features
- Sheer crochet fabric
- Checker pattern
- Open front with tie closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1978

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Get Spotted Cow Print Faux Fur Scarf
Get spotted in this cute cow print scarf as you walk downtown! The trendy scarf features an all-over cow print pattern on a super soft faux fur material. Style with the adorable hat.

Shop Matching Hat: Trendsetting Look Faux Fur Bucket Hat

Fit & Features
- Cow print pattern
- Faux fur material
Style Number/Barcode: 07305-0465

Category Name: Vacation Looks

Price: $4.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreamiest Summer Smocked Floral Chiffon Midi Dress
Have the dreamiest summer romance in this floral chiffon midi dress perfect for dates and parties! This dress features a square neckline, adjustable spaghetti straps, and a stretchy smocked bodycon silhouette for a comfortable and flattering fit. The tiered ruffled midi-length hem adds a touch of femininity, while the floral print on chiffon fabric gives the prettiest look. Style this floral dress with earrings and block heels.

Fit & Features
- Floral print, chiffon fabric
- Adjustable spaghetti straps
- Square neckline
- Stretchy smocked bodycon silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05101-2985

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cozy Elevated Faux Sherpa Trim Vest
This faux sherpa trim vest is a cozy elevated staple for the season! It features a lapel collar, an asymmetric zip-front design, a cropped hem, a fitted silhouette, and faux sherpa trims on the ultra-smooth faux suede fabric. Layer over a long-sleeved bodysuit with jeans and ankle booties for a chic fall vibe.

Fit & Features
- Sleeveless bodice, lapel collar
- Asymmetric zip-front design
- Two front faux pockets
- Cropped hem, fitted silhouette
- Faux sherpa trims
- Faux suede fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0395

Category Name: Vacation Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sun Chaser Stiletto Buckle Mules
Laid-back but luxe, these rafia mules were made for rooftop hotel brunches and dinners by the beach. The chic buckle detail and stiletto heel make them an easy upgrade to your weekend look.

Fit & Features
- Stiletto heel
- Square toe
- Wide dual straps, one with a buckle accent
- Cushioned insole
- Rafia material
- Runs true to size
Style Number/Barcode: 07401-000532

Category Name: Vacation Looks

Price: $34.90

Availability: In Stock

Available Color: BEIGE

Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
In Love Lace-Up Knee High Boots
Fall in love with these faux suede boots with endless styling possibilities! They feature an almond toe, inner zipper closure, a short block heel, and a knee-high shaft with a trendy lace-up back. Complete the look in a chic trench coat for a dinner and show downtown!

Fit & Features
- Almond toe
- Inner zipper closure
- Short block heel
- Knee-high shaft, lace-up back, tie closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0964

Category Name: Vacation Looks

Price: $12.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Blissful Aura Floral Ruffle Maxi Dress
Serve a blissful aura in this floral maxi dress while on vacation or for weekend fun! The delicate V-neckline accentuates your figure, while the form-hugging fit flatters your curves with a bold ruffled design.

Fit & Features
- Floral print, mesh fabric, sewn-in knit lining
- V-neckline, spaghetti straps
- Form-hugging bodice
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000054

Category Name: Vacation Looks

Price: $23.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling Cute Long Sleeve Open Back Catsuit
You'll be feeling cute in this flattering ribbed long sleeve catsuit. Enjoy the luxurious feel of the comfortable, form-fitting fabric as you show off the sultry open back, keep cozy with the fitted long sleeves and crew neckline with back button closures, and the perfect skinny-leg design. Complete the look in a jacket and cozy boots!

Fit & Features
- Fitted long sleeves
- Crew neckline, back button closures
- Open back
- Form-hugging
- Skinny-leg design
- Rib-knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06502-2397

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Day Dream High-Rise Wrap Mini Skirt
Look like a tropical day dream in this mini skirt while on vacation! The high-rise elasticized waistband ensures a comfortable fit, while the bodycon silhouette, wrap front design and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching top and pants.

Shop Matching Top: Tropical Day Dream Tie-Front Crop Top
Shop Matching Pants: Tropical Day Dream High-Rise Wide Leg Pants

Fit & Features
- Tropical print, stretchy knit fabric lined with knit
- High-rise elasticized waistband
- Bodycon silhouette
- Wrap front design
- Mini-length
- Runs true to size
Style Number/Barcode: 06501-0978

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Meadow Vibes Floral Eyelet Lace Mini Dress
Give your closet a dreamy meadow vibe with this floral mini dress - an adorable option for brunch and day dates! Featuring puff short sleeves, a sweetheart neck, front bust tie, and side ruched seam to accentuate your curves along the bodycon silhouette. The dress is composed of a ditsy daisy print on eyelet lace fabric with a stretchy knit lining. Complete the look in strappy sandals.

Fit & Features
- Puff short sleeves
- Sweetheart neck, front bust tie
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Ditsy daisy print
- Eyelet lace, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4945

Category Name: Vacation Looks

Price: $5.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Show Off Your Curves Smooth Knit Midi Skirt
This smooth knit midi skirt will show off your curves and create an alluring silhouette. It features a high-rise waist, a midi-length hem with a high-cut side slit accent, and a form-hugging fit to flaunt your figure. The ribbed smooth knit fabric includes a full-length knit lining and offers plenty of stretch. Style this mid-length skirt with a corset top and mules for happy hour.

Fit & Features
- High-rise elasticized waist
- Midi-length hem
- High-cut side slit
- Curve-hugging fit
- Ribbed smooth knit fabric, full-length knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0897

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Aura Sleeveless Sweetheart Eyelet Romper
You'll always charm with your sweet aura in this sleeveless eyelet romper perfect for wedding showers, graduations, or summer fun! Made of eyelet fabric, it's perfect for a sunny day with its short-length hem. Featuring a flattering sweetheart neckline and adjustable spaghetti straps, this romper also has underwire bust support and a fitted bodice to accentuate your figure. Complete the look with wedge sandals.

Fit & Features
- Eyelet fabric, stretchy knit lining
- Adjustable spaghetti straps
- Sweetheart neckline, underwire bust
- Back zipper and hook-eye closure
- Front hook and eye fasteners
- Short-length hem
- Runs true to size
Style Number/Barcode: 06303-0249

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Another Slay Sweater Knit Maxi Skirt
Another day, another slay! This sweater maxi skirt features an elasticized high-rise waist, a form-hugging silhouette, and a flirty center back slit along the hem on soft and stretchy rib knit fabric. Style the maxi skirt with a cute mini handbag and mules for a farmer's market!

Fit & Features
- Elasticized high-rise waist
- Form-hugging silhouette
- Center back slit
- Maxi-length hem
- Sweater rib knit fabric
- Soft and stretchy
- Runs true to size
Style Number/Barcode: 06501-0893

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Favorite Staple Striped Cutout Mini Dress
Slip into this striped mini dress with a flirty cutout and bodycon fit - it'll be your favorite staple all season long!

Fit & Features
- Striped pattern, stretchy rib knit fabric
- Strapless neckline
- Cutout accent
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000015

Category Name: Vacation Looks

Price: $38.90

Availability: Out of Stock
Product Badge:
- Ships Free
Raise The Heat Floral Mesh Off-Shoulder Top
Raise the heat with your bold allure in this floral mesh off-shoulder top! The asymmetric neckline and twisted straps add that trendy vibe to the fitted silhouette.

Fit & Features
- Mesh fabric, high stretch, sewn-in lining
- Large floral print
- Asymmetric off-shoulder neckline, twisted straps
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000062

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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