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  • by Urban Expressions
  • 4 min read

The itinerary is finalized, flights have been booked, and the countdown to your dreamy resort getaway has officially begun. But the big question remains: What are you going to wear? Now that’s a fun challenge we can’t wait to tackle! Whether you’re thinking of spending your vacation lounging by the beach and sipping piña coladas, exploring local attractions and cuisine, or partaking in all the adventures that await, we have the perfect look to match every setting. These 7 resort vacation outfit ideas and luxury purse recommendations are all about being effortlessly stylish and comfortable. Let’s dive right in!

1. A Flowy Sundress & A Quilted Bag

Woman in a flowy brown sundress & a red quilted bag

Nothing says “vacay ready” louder than a flowy sundress that moves with you. Think fit-and-flare silhouettes with deep V-necklines, ruffles, ditsy floral prints, fancy sleeves, and earthy natural hues. Pair it with strappy sandals and sleek gold jewelry to keep it minimalist and laid-back. A vegan leather crossbody bag that you can just sling across your shoulder and forget would be the perfect match for this resort outfit idea, adding to the practicality and comfort of the whole look. If you’re planning to wear this look in the daytime, don’t forget to add a straw hat!

2. A Schiffli Top & Shorts With A Straw Bag

Woman in yellow schiffli top & denim shorts holding a straw bag

Intricately designed schiffli tops are a staple when it comes to resort wear. Pair it with classic denim shorts, and you’ll have a breathable, easy-to-move-in outfit that’s great for everything from local market adventures to sunbathing on a lazy afternoon. Reach for tops in vibrant tropical colors, such as mustard yellow, emerald green, or rusty red. For accessories, go with espadrilles or flat sandals with a woven design and boho-themed jewelry, such as beaded necklaces, tasseled earrings, and seashell or stacked vegan leather bracelets. Finally, grab a woven purse made of a natural material, like straw, to tie the whole resort outfit idea together.

3. A Casual Midi Dress & A Large Tote

Woman in a white midi dress holding a brown tote bag

Need something casual but elegantly so? Then, a midi dress is just what you’re looking for. You’ll be surprised by how versatile a slightly fitted midi dress in a solid color, such as beige or cream, can be. If it’s sleeveless, you can wear it with a denim jacket and sneakers or flats when you want to go casual, or as it is with heels and statement jewelry for instant glam—perfect for daytime outings followed by dinner at the resort. This is one of those resort vacation outfit ideas you can elevate with just the right carry-all, like a vegan tote purse. It’s a no-brainer when you need to carry your things or you’re out buying souvenirs. During the evening, swap it for a statement handbag with more eye-catching details.

4. An Edgy Graphic Tee & Shorts With A Duffel Bag

Woman in a white graphic tee & black shorts holding a black duffel bag

When you want to look like you put some effort into your outfit without actually doing so, an oversized graphic tee paired with biker shorts is the solution. This duo combines the edgy vibes of streetwear and the comfort of athleisure, making it an ideal choice for sightseeing. Complete the look with sneakers and throw on a stylish hat. Lean into the sporty vibes of this resort outfit idea by styling it with a duffel bag. It’ll be a lifesaver for carrying water, snacks, sunscreen, and other essentials when you’re out on excursions.

5. A Classic LBD & A Sparkly Bag

Woman in a black mini dress holding a pearl-studded clutch

The dress code for resorts for evening or nighttime activities, like live shows and happy hours, is glam-chic, and you wouldn’t want to be caught underdressed while mingling with the other residents! A little black dress (LBD) is a classic that needs no introduction. You likely have one in your wardrobe right now. A-line and bodycon silhouettes are the most versatile. Style it with sparkly accessories such as rhinestone jewelry and a unique evening bag embellished with pearls, sequins, metal mesh, crystals, or beads. Any color except black would do! Complete this resort vacation outfit idea with strappy heels that steal the show.

6. Laid-Back Jeans & A Top With A Chic Backpack

Woman in a white tank top & jeans holding a brown backpack

The classic tank top and high-waisted jeans combo is always a winner, whether you’re wearing it in the city or at a fancy resort. It’s functional, stylish, and just what you need when you don’t want to stress too much about what you’re wearing and instead have a great time. Pair it with comfy sneakers and shrug on a vegan leather backpack so you can visit local hotspots hands-free.

7. A Comfy Athleisure Set & A Belt Bag

Woman in an ecru athleisure set with a green belt bag

A matching athleisure set is a must-have resort outfit idea whether you’re planning to stick to your workout routine or just want a comfy yet stylish look. An athleisure set is perfect for everything from high-energy activities to relaxed walks on the resort grounds to grabbing a cup of coffee in town. Layer it with a lightweight windbreaker jacket for extra practicality and top it off with sneakers. Want to stay hands-free and carry just the essentials? Grab a vegan belt bag or a vegan leather sling bag!

Resort vacations are all about relaxation, fun, and, of course, fabulous outfits! With these 7 outfit ideas and vacation bag recommendations, you’re all set for every part of your getaway. Remember to pack smartly and make the most of your time there!

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