20 Vacation Outfit Ideas: What to Wear on Vacation

I’ve always been a notorious last minute packer, especially when it comes to packing for vacation.

Years ago, on my first girls’ weekend in the Hamptons, I made the mistake of packing at the last second and not taking into consideration the destination.

I cut my packing so close to the train departure that I had to sprint over 15 crosstown blocks through the streets of NYC in a long maxi dress and sandals with my giant Longchamp duffle, only to make it onto the train right as the doors were closing (in fact they closed on the hem of my dress).

When we arrived, all my besties had beachy chic color palettes, and I, the typical New Yorker amongst us, had packed almost all black everything. 

I stuck out like a sore thumb until my girlfriends promptly lent me some of their lighter pieces to mix and match with my black ones.

After that, one of the first things I do is pick out a color palette for my destination (Instagram is a great tool for this).

These days, thanks to having go-to outfit combos and palettes for every destination, I end up successfully packing everything I need (even if I do occasionally over-pack). 

So in the spirit of packing earlier, I thought I’d share some of my go-to vacation outfit ideas, so that when it’s your turn to pack, you’ll know exactly what to wear on vacation.

I’ve broken things down into categories below to make packing for your next trip a breeze.

Things to Consider When Packing Vacation Outfits

Think About Your Plans

Before you pull any clothes out of your closet, sit down and think about the destination, any plans you have while there, and check out the weather report.

I always like to check out the places I’ll be on Instagram to get an idea of the local style, and to get ideas for places to eat or check out while I’m in town.

While I’m brainstorming, I make a list of things I absolutely know I’ll need while visiting.

Don’t Over Pack- Pick Things For Practicality

The thing I’m most guilty of is over-packing. This past summer, when I forced myself to live out of just a carry-on for three months, it forced me to really think things over and only pack the most practical items.

Sit down, make a list of practical things you cannot live without, then fill in any blanks with things you’d like to have but won’t need.

Or leave that extra space in your bag so that you’ll be able to do some shopping while on vacation!

Start With the Basics

When building your vacation outfits, start with the basic items you know you’ll be happy to have when building an outfit.

I always aim to bring pieces that are in the same color palette so that they can be mixed and matched easily to create new vacation outfits.

Basically, think monotone colors, classic t-shirts, and practical shoes. Plus any makeup or toiletry items you can’t go without. 

Add in a Fun Pieces

Once you have your basics laid out, add in a fun top or pair of heels that will make your outfit feel a bit more unique. 

I always bring at least one cool clutch, and some fun statement jewellery to add some pops of color to my outfits. 

Choose Shoes and Accessories Carefully

Whatever you do, don’t go overboard with unpractical shoes, or too many accessories.

The last thing you want is to use precious luggage space on a pair of heels you won’t want to walk in because they hurt your feet. Use that space to justify a bit of shopping instead!

Women’s Summer Vacation Outfits

White T-Shirt 

I always travel with at least one classic white t-shirt that you can dress up or down depending on the occasion.

This was one of my favorite wardrobe pieces this summer, when I packed three months of clothing into one carry-on suitcase. 

In fact, if you’re traveling long term, toss in a second white t-shirt for good measure!

Sundress

One of my favorite summer staples is a classic sundress, especially if it’s vintage!

I wear mine with comfy white tennis shoes during the day when I’m exploring, and pair it with leather sandals or heels for breezy nights out.

This is another one of those wardrobe staples you can dress up or down, depending on the vibe you’re going for.

You’ve also got the option of packing different lengths of sundress. I always keep a midi dress, and maxi on hand when I’m traveling for long periods of time.

Slip Dress

Silk slip dresses are one of my favorite summer outfits to pack because they barely take any room in your suitcase.

Not to mention, they’re also super comfortable, flattering for pretty much everyone, and look chic in photos.

They’re also super easy to style for low-key days or fancy date nights.

Linen Button Down

A light linen button down is a must for summer beach vacations.

It’s super versatile and makes a great beach cover-up in a pinch.

I’m partial to a white linen button down, but go with what color speaks to you the most. 

Pro Tip: Hang up your button down the second you arrive. Linen is super chic but wrinkles like crazy. If you need to wear it quickly, hang it in the shower and let the steam from the shower get the wrinkles out.

Classic Tank Top

There’s nothing I love more than my summer tank tops. I always pack a couple in basic colors like white, cream, brown, or black.

They’re super easy to pair with a skirt or shorts, plus they always look great in photos.

If you’re feeling it, pack a cropped tank top for a bit of a sexy vibe! I always have at least one with me to pair with my high waist jeans.

Cut-Off Shorts

Cut-off shorts are another summer classic that everyone should have in their closet.

I’d bring at least pairs with me for a trip that’s a week or longer. 

When I went to Europe this summer, I went for a dark wash denim pair, and a white pair. Between the two styles, I could create a ton of different summer vacation outfits.

Classic Jeans

Okay, obviously long jeans will not be the first thing on your summer vacation packing list, but hear me out—they deserve a spot on your packing list!

Summer nights cool off, and what better way to stay warm than with a pair of classic blue or white jeans.

They’ll pair well with all the tops we’ve talked about, plus look great in photos.

Pro Tip: I always default to wearing mine on the plane, so that they don’t take up a bunch of room in my suitcase.

Mini Skirt

Mini skirts are a classic and sexy summer staple. 

I always pack a denim one that can I can wear with tennis shoes or sandals during the day and dressed up at night with a pair of cute wedges.

Maxi Skirt

One item I wished I had packed when I got over to Europe was a maxi skirt.

When those nights cool off or the day’s windy, nothing is better than throwing on a long maxi skirt to keep warm.

Plus, if you bring a really flowy maxi skirt, it’ll look gorgeous in photos as the wind makes it billow out behind you. 

Relaxed Trousers

Basically cropped trousers are perfect for those summer trips where the weather is a bit unpredictable.

A pair of classic trousers will always look chic, especially running around during the day with tennis shoes. They’re also great when going out to a restaurant that blasts the AC.

Versatile Sandals

Sandals are easily my favorite type of shoe. There are so many varieties to choose from that you can pick one that shows your unique sense of style.

If you’re only going away a few days and can bring multiple pairs, I highly suggest having fun and packing lots of colorful options, including a pair of heeled sandals.

If you’re packing for a lengthy trip, though, I’d keep things simple and pack two pairs of leather sandals in basic colors that work with your color palette, so that they’ll go with every outfit in your bag.

For example, when I went to the French Riviera and Greece over the summer, I only packed a classic flat black pair and a pair of white sandals. As much as I wanted to have a pair of heels on hand, I knew it wasn’t practical for the terrain I’d be exploring.

Fashionable Sneakers

Last summer, when I was getting ready to head over to spend the summer in Europe, I spent hours searching for the perfect pair of classic and fashionable sneakers.

I knew I could only bring one pair, since my goal was to live out of just my Away Bigger Carry-On suitcase.

After searching through tons of brands, I eventually ended up settling on a pair of classic leather platform Keds. They looked great in photos, plus were totally comfy and chic.

The only downside is that I almost twisted my ankle a few times when hitting uneven ground while exploring. Some people can gracefully wear platforms, but I was quickly reminded I can only wear them on certain occasions.

If you’re planning on running around on uneven terrain, I’d suggest you go for a classic sneaker that doesn’t have a platform and offers enough traction on the bottom to keep you from slipping.

Sunglasses

Classic black sunglasses are my all-time favorite accessories.

They instantly upgrade any outfit, plus hide your eyes on days you’re hungover or didn’t get around to putting make-up on.

Everyone should always have at least one pair of classic sunglasses on hand. Bonus points if you bring a second fun pair along! 

Hat

I love a good straw fedora or floppy beach hat on vacation. 

It always looks chic, keeps your hair in place (or hides greasy hair if you don’t have time to shower), and will keep the sun off your face.

Plus, it’ll look great in Instagram photos!

Statement Accessories

Since you’re packing basic clothes, it’s fun to have a few statement accessories on hand to dress up your outfits and make them feel a bit more unique.

I always carry a statement necklace and bracelet with me, a belt, maybe a watch, plus one or two cocktail rings to add a bit of glamour to an outfit. 

Obviously, just don’t wear all the statement accessories at once! You don’t want to look like you’re trying too hard. After all, beachy chic is all about subtle details.

Classic Tote Bag and Small Purse

I always travel with my classic champagne Longchamp tote bag.

It matches everything, can easily double as a beach bag, and fits a ton of stuff, which is perfect for little day trips to neighboring beach towns.

You’ll also want a cute little bag that you can take out to dinner with you. I try to bring one that’s a fairy neutral color so it matches all my outfits.

If you have the space, you should also pack a cute wicker basket bag. I became a bit obsessed with them this summer in Antibes. All the ladies walk around them, especially when going to the market or the beach. 

They’re so chic! Unfortunately for me, they’re also quite annoying to fly with, as you basically need to use it as your personal item, since they’re hard to pack without breaking.  

Men’s Summer Vacation Outfits

Classic Well Cut T-Shirt

A classic t-shirt can go a long way!

Between rocking it at the beach, on a run, or even to dinner, this item will serve you well.

In terms of the neckline, you can choose a v-neck or crew cut. You could even do a polo if you need to dress up a bit.

You’ve got to have a classic white shirt, plus pack a couple of others in beachy chic tones to complete your vacation look.

Classic Jeans

Everyone loves a good pair of jeans, especially ones with a classic cut and wash.

Bring a pair of jeans that are cozy enough to wear around town during the day, and a dark enough wash to dress up a bit in the evening.

Linen Button Down

Gentleman, you can’t go wrong with a nice linen button down.

The material is light and breathable, so you won’t be dying from the heat. Plus, you can easily dress this top up or down depending on what kind of vibe you’re going for.

Just hang it up the moment you arrive at your destination. Linen is notorious for wrinkling! 

If you’re in a hurry to wear it, you can always hang it in the bathroom with the shower on as hot as it will go. The steam should hopefully get most of the wrinkles to fall out quickly.

Shorts

Recently, my fashion blogger friend Hailey gave me some advice while buying my boyfriend some new shorts for our upcoming vacation—short shorts are now in style for guys.

I was definitely a bit thrown because the first thing that came to my mind was extremely short cut-offs. Thankfully, that’s not what she meant!

Hailey told me to find some tailored 5-7″ shorts for him to try, and I’ve got to say they look fabulous!

They come in a variety of styles, including chino shorts and athletic ones. I suggest bringing a pair of both with you, so you’ll have a casual option and a more upscale one.

Either way, both options will pair perfectly with a fitted t-shirt.

Trust me, when you try them on, you will see your style transform from bland to chic. Just don’t forget a belt for when you want to dress up you’re look a bit!

Sandals

Gentleman, invest in at least one solid pair of leather sandals. 

Trust me, you’ll get plenty of wear out of them on vacation.

Sneakers

A pair of quality sneaks will keep your feet happy all day long as you venture out to explore whatever sunny destination you’ve found yourself in. 

I’m a big fan of a classic white sneaker, but let your personal style influence the type of sneaker you go for.

Sunglasses

Obviously, in any summer vacation destination, there’s going to be a ton of sun. 

Do yourself (and your eyes) a favor and pack at least one pair of classic sunglasses.

I’m partial to the aviator look on men, but go for whatever style makes you feel cool!

Accessories

Don’t forget to bring a belt or two, a watch, and maybe a backpack to tote around to the beach or on little day trips.

Beach Vacation Outfit Essentials

Besides the obvious summer vacation essentials you’ll want with you at your sunny destination, you’ll also want a few of the beach essentials below.

Swim Suit

This one should be obvious if you’re going to the beach.

Depending on how many days you’re going, I’d bring between two and four suits, with at least one of those suits being a one piece.

I always bring at least two, so I have a dry one to put on in case my first suit is still damp from swimming.

If you’re going to be on the beach all week, four suits are perfect. This way, all your photos won’t look the same. Plus, you’ll definitely want to switch up your beach style depending on where you’re going.

For the guys in the crowd, the same rules apply, bring at least two pairs of swim trunks.

Swim Cover-Up 

I’m notorious for forgetting to pack a proper swim cover-up. 

I can’t tell you how many times I’ve had to borrow them from friends when it was necessary to wear one to a trendy beach club. 

These days, I always keep at least one cute white cover-up or colorful wrap with me when I travel.

I don’t think you’ll need a ton of proper swim cover-ups, after all shorts and t-shirts totally work on most beaches. 

But it’s always good to have one proper swim cover-up in case you want to hit up a fancy beach club.

Gentlemen, you’ve lucked out with this one, since all you’ll really need is a cool shirt to go with your swim trunks.

Tote Bag

Honestly, having a tote bag should be a requirement on any trip, but especially the ones that involve the seaside.

I always use mine as my personal item on quick trips. For longer ones, I’ll fold up my Longchamp and leave it at the top of my suitcase for easy access.

Tote bags are so easy to carry everything you need for the day, including a towel or beach blanket, plus your kindle, sunscreen, change of clothes and wallet.

Flip-Flops

After ruining a pair of chic leather slides on sandals last year at the beach, I’ve resolved to always keep a pair of flip-flops on hand for the beach.

I know they aren’t always the most stylish, but trust me, they’re so much easier to toss on in a hurry when you’re hitting the pool or beach.

Save those stylish leather sandals for nights out!

Sunglasses

Obviously, sunglasses are a must in sunny locations, but especially when laying out in the sun.

I normally just travel with one pair of classic black sunnies, but if you’re going to be gone a while, and want to mix things up, it doesn’t hurt to have a second more fun pair. 

Silk Scarf

After seeing all the cool French girls wearing silk scarves at the beach while I was living in the French Riviera last summer, I’ve been totally in love with this accessory.

You can use it as a headband or headscarf at the beach to keep your hair tamed in the wind. You could use it as a wrap in a pinch, or even put it around your neck or shoulders if the weather cools off.

I think silk scarves at the beach will continue to become a big trend, so get ahead of the curve and start rocking one on your next beach vacation.

Hat

This one is pretty obvious, even if it is a total pain to pack.

You’ve got a few options in terms of style. You can go for a classic tennis cap or visor, a straw fedora, or a floppy beach hat (my favorite).

If you really want to go out on the edge style-wise, you could also try the recently popular bucket hat trend (thanks, Emily in Paris).

Go ahead and just wear your hat on the plane to make your life easier. 

If you’re bringing more than one floppy beach hat, just layer them on top of your head until you get to the plane and then put them in the overhead. 

I know you’ll look a bit nuts, but honestly, I see so many people doing this that I doubt you’ll be the only one.

Gentlemen, obviously you’ll want to just go with a classic sports cap, or maybe even a fedora if you really want to make a statement

Sunscreen

I can’t tell you how many times I’ve gone on vacation and forgotten to pack sunscreen.

The last time I did, I was at a resort in Turks and Caicos and ended up spending over $50 on the only sunscreen they had in the gift shop. 

Don’t end up repeating my mistake, just order some quality sunscreen from Amazon before your trip. It’s easy, and your skin will thank you later!

Just don’t forget to re-apply regularly at the beach. The last thing you want to do is burn or expedite your skin’s aging process!

Chapstick

Okay, I know this one seems random, but you’ll want a moisturizing chapstick with SPF to keep your lips hydrated and protected while you’re having fun in the sun.

I always keep a chapstick in each of my bags to make sure I’ve got easy access to re-apply at any hour of the day.

Wrapping Things Up

I hope this guide helps inspire some truly fabulous vacation outfit ideas for you.

Just remember, don’t over pack. You can always go shopping during vacation for anything you forgot!

Let me know in the comments below what your favorite vacation outfit is!