March 27, 2025
10 Versatile Vacation Outfit Ideas for Every Adventure
We don’t know about you, but for us, vacation starts the moment we start planning our looks. The anticipation of sunny days, new places and new adventures make every detail exciting — including what to wear. And while packing can sometimes feel like a chore, figuring out what to wear on vacation and planning your vacation styles can be part of the fun.
But with limited packing space also comes limited decisions when it comes to one of the most important parts of your looks: shoes. Bringing too many pairs with you can take up valuable space in your suitcase, but not having the right ones can leave you uncomfortable or unprepared. The secret is choosing comfortable travel shoes that work with multiple outfits and can handle whatever your trip has in store.
That’s what makes TOMS the perfect shoes for travel. With resort-ready styles that are easy to pack, comfortable and stylish, you’ll have the best vacation wardrobe for everything from sightseeing to sunset dinners. Read on for our favorite vacation outfit ideas featuring shoes that keep up with every adventure.
1. Wrap Skirt, Colorful Tee and Espadrilles
If you’re looking for resort vacation outfit ideas that can take you from all-day shopping to a sunset stroll, a wrap skirt with a colorful tee is an easy way to stay comfortable and beat the heat while also looking chic and trendy. The wrap skirt is super versatile, working both as a coverup and a stylish piece you can wear for dinner. Pair it with a pair of espadrilles to keep it casual but still put-together and throw on some simple jewelry or a woven bag to elevate the look.
Styling Tip: Go for a wrap skirt in a lightweight fabric that moves easily and packs well. A cropped or fitted tee works best to balance out the skirt’s shape. If you want to dress it up a bit more, swap the tee for a linen button-down tied at the waist. Want more tips? Read our guide to learn how to style espadrilles.
2. Crochet Maxi Dress and Wedge Sandals
For vacation attire ideas that bring attitude but still work for restaurants and evening plans, a crochet maxi dress is the way to go. Crochet anything is great for vacation because the open-knit design gives them a relaxed, beachy feel while the heavier fabric makes them that perfect in-between outfit — casual during the day and elevated when you want to dress up. Wedge sandals add a little height without the boldness of stilettos, making them a great match for this kind of dress.
Styling Tip: Layer a slip dress underneath for more coverage, or wear it over a swimsuit for a daytime look that transitions easily to dinner. A sleek bun or loose waves will complement the vacation-ready vibe.
3. Denim Shorts, White Linen Top and Floral Alpargatas
Linen is the ultimate warm-weather vacation staple. Denim shorts and linen shirts can be styled in countless ways, so they’re always worth packing. They’re appropriate for almost any plan, from exploring local markets to grabbing lunch by the water, and pairing them with floral alpargatas brings in a fun, playful element to the ensemble.
Styling Tip: For a cute and easy resort outfit idea, tuck in the linen top and add a woven belt to define the waist, or leave it untucked for a more relaxed feel. Layered gold jewelry and a straw tote complete the look.
4. Maxi Skirt, Graphic Tee and Platform Sneakers
Some vacation days call for closed-toe shoes, especially when there’s a lot of walking involved or the plan includes something beyond lounging by the beach. A maxi skirt with a graphic tee is an easy way to stay comfortable without looking too casual, and platform sneakers pull it all together with an elegant lift. Perfect for exploring new cities, checking out local shops or grabbing a coffee before heading to your next adventure. Discover more ways to style platform sneakers here!
Styling Tip: Knot the tee at the waist or side for a little shape or French tuck it in for a trendier moment. If the skirt has a bold print, a simple tee balances it out.
5. Cutout Dress and Textile Heels
Textile heels and a chic cutout dress are the perfect pair for when you’re looking for summer vacation outfit ideas that look elevated but only take a second to put together. Perfect for anything from dinner by the water to a night out at the local watering holes, this duo is an easy choice when packing space is limited but you’ve got big plans for the night.
Styling Tip: Neutral heels keep it classic, while a bold color adds some fun. A small clutch and delicate jewelry complete the look without competing with the dress.
6. Black Midi Dress and Lace-Up Sneakers
A black midi is one of those pieces that always works, no matter the destination. It’s flattering, looks put together without any extra effort and transitions easily from day to night. For shoes, lace-up sneakers keep it practical, especially for days filled with walking. They also give the dress a laid-back feel that makes it even more wearable. Want something a little more refined but still casual? Pack a pair of slip-on platforms for a little extra oomph.
Styling Tip: A denim jacket over the shoulders adds an extra layer for cooler evenings. If the dress has a fitted silhouette, try hi-top sneakers for a fun contrast. Discover more casual sneaker outfits here!
7. Cardigan, White Shorts and Slingback Sandals
Balance is the best ingredient for the perfect vacation outfit, like pairing a lightweight cardigan with a pair of crisp white shorts. Even if you’re heading somewhere tropical, cardigans are a must for vacations — not only because they add some coverage the breeze picks up, but also because they instantly elevate any outfit. A crochet style keeps it light and airy so it won’t feel too warm during the day, while a chunkier knit cardigan is great for cooler days. Paired with white shorts and slingback sandals the whole look feels fresh, easy, and just polished enough for whatever’s on the itinerary. Need sandals for a long day on the go? Check out our favorite sandals for walking!
Styling Tip: A cropped cardigan creates a more modern feel, while an oversized one leans into that summery vibe. To accessorize, a woven tote or a simple pendant necklace adds the perfect finishing touch.
8. Short-Sleeve Button Down, Linen Shorts and Mules
The best beach vacation outfit ideas are the ones that allow you to get in and out of the water and into whatever else you’ve got planned in a pinch. And a short-sleeve button-down with linen shorts does just that! This look is cool, casual and vacation-vibes effortless. For shoes, opt for something as easy to get in and out of, like mules or alpargatas, for an ultra-chic look.
Styling Tip: Leave a couple of buttons undone and roll the sleeves once or twice for a fitted silhouette. Add a cute beach bag and a simple chain necklace for just the right amount of detail.
9. Drop-Waist Dress and Mary Janes
Certain vacation events, like a cruise dinner or a party with a dress code, call for something a little dressier. For times like this, your best option is to go for a dress that feels elevated without being too stuffy, like a classic drop-waist number. Rope-sole heels bring that beachy vibe while Mary Janes are a stylish alternative that still feels dressy without any discomfort.
Styling Tip: A structured mini bag and delicate gold hoops refine the look. Try ankle socks with the Mary Janes for a fun, fashion-forward detail.
10. White Denim Romper with Slip-Ons
Rompers are as easy as it gets during vacation — one piece and you’re done. A white denim romper is casual but still looks fresh and refined, so it’s a nice option for everything from browsing local shops to grabbing a sunset drink. Slip-ons in a fun color or print make it even better, giving you that wear-all-day ease without thinking twice about it. Discover the best slip-on shoes for all-day comfort.
Styling Tip: Layer on a few stacked rings or add a fun scarf for a little extra detail. Toss on a straw hat or baseball cap to keep the look vacation-ready and practical for sunny days.
Must-Haves for Styling Vacation Looks
When putting your vacation outfit ideas together, keep in mind that it’s the little details that complete the look. Packing a few extra pieces will help switch up outfits without taking up a ton of space in your suitcase:
- Jewelry: Gold hoops, layered necklace or a statement ring can bring that little something extra.
- Handbags: A woven beach bag for daytime, a clutch for evenings and a crossbody for everything in between.
- Sunglasses: No vacation is complete without the right pair of sunglasses. They’re both a sophisticated accessory and a necessity for sunny destinations.
- Hats: A straw hat or a sporty cap adds character and offers some much-needed sun protection.
- Belts: To cinch a flowy dress, define the waist of a romper or add interest to a simpler look.
- Scarves: Tie one around your neck, in your hair to protect it from the sun or on your bag for an easy way to switch things up.
Remember, your clothes set the foundation, but it’s the accessories that add personality and flair. Now that you have vacation fashion inspo and a list of essentials, get stylin’!
Wear TOMS. Wear Good.
Hopefully, these vacation outfit ideas make packing a little easier. With the right pieces and a few accessories, putting together stylish, travel-ready looks doesn’t have to be a headache. No matter the destination, the TOMS vacation collection has shoes that fit the occasion. From espadrilles for beach days, slip-ons for sightseeing and heels or wedges for dinner plans, we have something for everyone.
Beyond great style and comfort, when you choose TOMS you support something bigger. Every purchase helps fund community programs focused on mental health resources, education and grassroots initiatives that create real change. So packing a great pair of shoes also means doing good along the way. Learn more about our impact.
Shop our women’s shoes to find the perfect pair today!