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Vacation Outfits

336 products

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Lucy Polka Dot Midi Dress
Lucy Polka Dot Midi Dress

By Princess Highway Lucy Polka Dot Midi Dress

$79.60
🖤 SALE *Price as marked
Passionfruit Shirt

By Princess Highway Passionfruit Shirt

$62.80
🖤 SALE *Price as marked
Casino Block-Heel Sandals
Casino Block-Heel Sandals
Casino Block-Heel Sandals
Casino Block-Heel Sandals

By Chelsea Crew Casino Block-Heel Sandals

$39.50 $79.00
👠 Chelsea Crew SALE *Price as marked
Grand Leather Comfort Flats
Grand Leather Comfort Flats
Grand Leather Comfort Flats
Grand Leather Comfort Flats

By Chelsea Crew Grand Leather Comfort Flats

$30.00 $79.00
👠 Chelsea Crew SALE *Price as marked
Cybil Open Back Loafers
Cybil Open Back Loafers
Cybil Open Back Loafers

By Chelsea Crew Cybil Open Back Loafers

$30.00 $75.00
👠 Chelsea Crew SALE *Price as marked
 

By Orchid Bloom White Lemon Halter Swing Dress

$89.00
Harvard Pant
Harvard Pant

By Princess Highway Harvard Pant

$72.60
🖤 SALE *Price as marked
Samira T-Strap Sandals
Samira T-Strap Sandals
Samira T-Strap Sandals

By Chelsea Crew Samira T-Strap Sandals

$32.00 $79.00
👠 Chelsea Crew SALE *Price as marked
Olga Slingback Sandals
Olga Slingback Sandals
Olga Slingback Sandals

By Chelsea Crew Olga Slingback Sandals

$32.00 $79.00
👠 Chelsea Crew SALE *Price as marked
Wilson Slip On Sneakers
Wilson Slip On Sneakers
Wilson Slip On Sneakers
Wilson Slip On Sneakers

By Chelsea Crew Wilson Slip On Sneakers

$47.40 $79.00
👠 Chelsea Crew SALE *Price as marked
Maxine Check Midi Skirt 100% Cotton

By Princess Highway Maxine Check Midi Skirt 100% Cotton

$69.80
Woody Loafers
Woody Loafers
Woody Loafers

By Chelsea Crew Woody Loafers

$47.40 $79.00
👠 Chelsea Crew SALE *Price as marked
Cage Fisherman Sandals
Cage Fisherman Sandals
Cage Fisherman Sandals
Cage Fisherman Sandals

By Chelsea Crew Cage Fisherman Sandals

$89.00
Bali T-Strap Sandals
Bali T-Strap Sandals
Bali T-Strap Sandals

By Chelsea Crew Bali T-Strap Sandals

$30.00 $69.00
👠 Chelsea Crew SALE *Price as marked
 

By Orchid Bloom Lemon Print Swing Dress

$99.00
Trigg Leather Flat Slides
Trigg Leather Flat Slides

By Chelsea Crew Trigg Leather Flat Slides

$34.50 $69.00
👠 Chelsea Crew SALE *Price as marked
Olympia Suede Mules
Olympia Suede Mules
Olympia Suede Mules

By Chelsea Crew Olympia Suede Mules

$30.00 $79.00
👠 Chelsea Crew SALE *Price as marked
Garden T-Strap Flats
Garden T-Strap Flats

By Chelsea Crew Garden T-Strap Flats

$30.00 $69.00
👠 Chelsea Crew SALE *Price as marked
Gadget Multi-Strap Flats

By Chelsea Crew Gadget Multi-Strap Flats

$30.00 $59.00
👠 Chelsea Crew SALE *Price as marked
Light Blue & White Polka Dot Swing Dress

By Orchid Bloom Light Blue & White Polka Dot Swing Dress

$99.00
Jarden Suede Scallop Sandals
Jarden Suede Scallop Sandals
Jarden Suede Scallop Sandals

By Chelsea Crew Jarden Suede Scallop Sandals

$30.00 $79.00
👠 Chelsea Crew SALE *Price as marked
 

By Orchid Bloom Red & White Picnic Swing Dress

$99.00
 

By Orchid Bloom Blue Plaid Swing Dress

$89.00
Black Candy Halter Swing Dress

By Orchid Bloom Black Candy Halter Swing Dress

$89.00
Costa Platform Slides
Costa Platform Slides
Costa Platform Slides
Costa Platform Slides

By Chelsea Crew Costa Platform Slides

$35.00 $89.00
👠 Chelsea Crew SALE *Price as marked
 

By Orchid Bloom Black & Red Cherry Halter Dress

$89.00
Lottie Mini Skirt

By Princess Highway Lottie Mini Skirt

$62.80
🖤 SALE *Price as marked
Cuban Leather Sandals
Cuban Leather Sandals
Cuban Leather Sandals

By Chelsea Crew Cuban Leather Sandals

$25.00 $95.00
👠 Chelsea Crew SALE *Price as marked
Daisy Retro Heels
Daisy Retro Heels

By Chelsea Crew Daisy Retro Heels

$77.40 $129.00
👠 Chelsea Crew SALE *Price as marked
Debbie Wedged Sandals
Debbie Wedged Sandals

By Chelsea Crew Debbie Wedged Sandals

$65.40 $109.00
👠 Chelsea Crew SALE *Price as marked
Hollie Wooden Platform Heels
Hollie Wooden Platform Heels
Hollie Wooden Platform Heels

By Chelsea Crew Hollie Wooden Platform Heels

$53.00 $99.00
👠 Chelsea Crew SALE *Price as marked
Monday Leather Tennis Sneakers
Monday Leather Tennis Sneakers
New

By Chelsea Crew Monday Leather Tennis Sneakers

$99.00
Slick Ballet Flats
Slick Ballet Flats
Slick Ballet Flats
Slick Ballet Flats
Slick Ballet Flats

By Chelsea Crew Slick Ballet Flats

$119.00
La Fraise Blouse

By Princess Highway La Fraise Blouse

$62.80
🖤 SALE *Price as marked
Chickens Short Sleeve Blouse

By Princess Highway Chickens Short Sleeve Blouse

$65.60
 

By Orchid Bloom Blue Checker Swing Dress

$89.00
 

By Orchid Bloom Prince Lily Floral Swing Dress

$89.00
 

By Orchid Bloom White Red Cherry Halter Swing Dress

$89.00
 

By Orchid Bloom Yellow Floral Swing Dress

$89.00
 

By Orchid Bloom Yellow Floral Swing Dress

$89.00
Llama V Neck Sleeveless Dress

By Princess Highway Llama V Neck Sleeveless Dress

$79.60
🖤 SALE *Price as marked
 

By Orchid Bloom Pink Plaid Swing Skirt

$79.00
 

By Orchid Bloom Off White Plaid Swing Skirt

$79.00
Red Candy Halter Swing Dress

By Orchid Bloom Red Candy Halter Swing Dress

$89.00
 

By Orchid Bloom Blue Checkmate Swing Dress

$89.00
 

By Orchid Bloom Pink Royall Ballet Swing Dress

$99.00
Miami Retro Dad Sneakers
Miami Retro Dad Sneakers
Miami Retro Dad Sneakers
Miami Retro Dad Sneakers

By Chelsea Crew Miami Retro Dad Sneakers

$71.20 $89.00
👠 Chelsea Crew SALE *Price as marked
 

By Orchid Bloom Martina Cherry Swing Dress

$99.00

Vacation Outfits & Resort Wear for Women

Out of office starts with the outfit. The Vacation Shop is filled with getaway-ready styles designed for beach days, city strolls, cruise adventures, and every postcard-worthy moment in between.

From breezy vacation dresses and lightweight separates to playful rompers, resort-ready sandals, statement sunglasses, and packable accessories, this collection makes it easy to build a suitcase you'll actually be excited to unpack. Think colorful prints, easy silhouettes, and versatile pieces that work from sightseeing and brunch to sunset dinners and spontaneous detours.

Whether you're planning a tropical escape, a weekend road trip, a European adventure, or simply dressing like one is on the calendar, you'll find vacation outfits, resort wear, cruise outfits, and beach vacation clothes designed to travel beautifully and wear effortlessly. With vintage-inspired charm, vibrant personality, and plenty of mix-and-match potential, these styles are ready wherever the itinerary takes you.

Because the best souvenirs are the photos where you loved your outfit.

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