Dresses To Wear On Vacation

Vacations are the perfect time to relax and enjoy yourself. But while you’re relaxing and having fun, you still need to dress appropriately for the occasion.

That doesn’t mean you have to wear a suit. It just means that wherever you go, you’ll want to make sure that your clothes are comfortable and appropriate for the situation.

When you’re traveling, it can be hard to know what to wear. You want to look cute, but you also want to be comfortable. And you don’t want to have to worry about your outfit all day long.

Here are some cute outfits for traveling that will keep you comfortable and stylish during your vacation.

Tropical Outfits

A maxi dress or skirt is a great option for when you’re traveling somewhere tropical. It’s easy to move around in, and the breezy fabric keeps you cool in hot weather. Plus, it’s easy to throw on over your swimsuit when you’re going out to dinner or the beach after a day at the beach.

Pair any of these looks with some flat sandals or wedges and a floppy hat if necessary!

Dresses To Wear On Vacation

Stylists Plan the Perfect Vacation Outfit

Stylists Say These 15 Pieces Are All You Need to Pack For Cute Summer Vacation Outfits

When the coronavirus hit, the world as we knew it came to a staggering halt. This time last year, we couldn’t even leave our houses, let alone jet-set off to a tropical resort. Now, in the midst of #shotgirlsummer, scoring a hotel room near the water feels like winning the lottery. But, if you thought planning that long-awaited trip was a challenge, you clearly haven’t started packing your vacation outfits yet.

While quarantining may have taught us a lot about the fashion choices we make on a daily basis (i.e. that bras are actually optional and wearing tight pants that look good but feel restricting is actually outrageous), it taught us virtually nothing about packing for vacation fashion. However, if we’ve learned anything from refusing to pay for excess luggage, it’s that you don’t need to overpack in order to have a ton of options. What you need are a few key pieces that can be mixed and matched to create multiple outfits.

Below, we’ve rounded up a list of must-have vacation fashion items recommended by renowned stylists. Together, their picks create the ultimate vacation capsule wardrobe that allows you to save room in your suitcase and have a ton of day-to-day options to choose from, no matter how long your stay.

1. A Cropped or Traditional White Tee

Stylists Plan the Perfect Vacation Outfit

When packing for vacation, celebrity stylist Tara Swennen tells InStyle you want to choose neutral colors for the base of your looks, and a cropped or traditional white tee is a perfect example. “These pieces can be layered as much as possible go with just about anything – knit pencil skirts, drawstring linen pants, overalls, high-waisted jeans… the list goes on and on,” Swennen says. “They are truly the most versatile and lightweight piece to bring!”

Shop now: x karla The Crop Tee; $48

2. Cropped Trousers

Cropped Trousers

Contrary to popular belief, you don’t have to pack bottoms of every shape and color when going on vacation. To keep things simple, Swennen says she likes to stick with three pairs of pants in three basic colors, so that she can mix and match them with other neutral or fun pattern tops throughout her stay.

“A black, white and neutral pair will carry to just about anything and can be styled day to night by simply swapping a thing to a heel,” she tells us. “I like linens, crepes, or a stretchy fabric that don’t wrinkle easily and therefore can carry you through a few occasions!”

Shop now: Theory Wide Leg Crop Pants; $325

3. A Bucket Hat

Vacation Fashion

You can expect your summer 2021 wardrobe to be inspired by the ’90s, starting with the bucket hat — aka, the perfect accessory to block out the sun or to add a bit of panache to your polo shirt and trousers, according to fashion stylist Mickey Freeman.

“Bucket hats are giving men and women of all ages and walks of life shade while keeping them ‘cool,'” he tells InStyle. “It’s once again getting its time to shine — while blocking it of course!”

4. A Multi-faceted Mini Skirt

Mini Skirt

Raise your hand if you’ve ever worn a mini skirt as a shirt. If not, celebrity stylist, Britt Theodora, highly recommends giving this (brilliant) hack a try.

“I love two-in-one pieces especially if you are packing a carry-on,” Theodora says. “I would style [a skirt] with linen high-waisted pants if I were wearing it as a shirt. If wearing it as a skirt, I would style it with a tie-at-the-tummy button-up shirt!”

Shop now: Hunza G Mini Skirt; $118

5. A Pair Of Blue Jeans

Vacation Outfits

Blue jeans and white tees go together like pool bars and bay breezes, but Swennen assures InStyle that a pair will get much more than one use on your vacation.

“Blue jeans are extremely versatile. Wear them with a loose-fitting blouse, a T-shirt, a duster for an early evening stroll, or with a sexy, tight, knit top for a night on the town,” she says.

6. Cutoff Shorts

Stylists Plan the Perfect Vacation Outfit

While we’re on the subject of denim, cutoff shorts are another great example of a piece that can easily be dressed up or down. To do this, Freeman suggests using cool accessories like stacked bracelets or necklaces to your advantage.

Shop now: Good American ’90s Bermuda; $99 (Originally $129)

7. A Sundress


By simply swapping flip-flops for a pair of sexy strappy heels or even a boot, Swennen says that sundresses can be your perfect done-in-one day-to-night piece for a summer vacation.

“Pair with a belted blazer, layer with a fun sweater or wrap for evening or silly keep it casual wedges and a fun tote! It’s a summer must!”

8. A Linen Button Down

Stylists Plan the Perfect Vacation Outfit

Button-downs make for great tops, but they also make for great accessories as well. Theodora says she loves throwing an oversized men’s fit “over bathing suits, with jean shorts or unbuttoned over a dress for when it gets cooler at night.”

9. A Statement Accessory

Stylists Plan the Perfect Vacation Outfit

While you may not need to stuff five pairs of shoes into your suitcase, according to Swennen, a statement accessory that demands attention is non-negotiable.

“This could be as simple as a vintage chain Chanel belt or an amazing collar necklace,” she tells us. “This will be the one thing that helps elevate your daytime look to a fun evening occasion.”

10. Rope Sandals

Stylists Plan the Perfect Vacation Outfit

Speaking of footwear, as far as Theodora is concerned, rope sandals should be a staple in your vacation wardrobe.

“These Isabel Marant shoes have been a staple for me this summer. They are incredibly comfortable and can elevate your go-to jean shorts and tank tops this season,” Theodora tells InStyle. “I love styling pops of colors with my outfits and these shoes are great for mixing it up!”

11. A Swim Coverup

Stylists Plan the Perfect Vacation Outfit

The one-piece to pack for any warm-weather vacation would have to be a coverup, says Aerie director of styling, Erin Collins Rittling, who suggests this one as the perfect pick.

“Designed to take you to the beach and beyond, the right coverup is perfect to throw over a swimsuit during the day or can be dressed up for a night out by adding a touch of jewelry or embellished headband.”

Shop now: Aerie V Cover Up; $40

12. A Wicker Tote

Stylists Plan the Perfect Vacation Outfit

Straw totes were all the rage in 2020, and in 2021 you’ll have more opportunities to rock them outside the homestead, especially if you’re going on vacation. According to celebrity stylist, Tyler Minor, wicker totes are the “it” vacation back because they’re so versatile.

“These handbags are great to hold your towel and SPF at the beach or throw a fun scarf around the handle and take it to a fabulous lunch.”

Shop it: Pigeon & Poodle Elko Tote; $230

13. Birkenstocks Sandals

Stylists Plan the Perfect Vacation Outfit

Love them or hate them, Birkenstocks are making a comeback for summer 2021, and Freeman is vouching for them as a vacation must-have.

“Now available in new and fun monochromatic colorways, this lightweight and comfortable sandal is a perfect way to balance out a sexy swimsuit with a semi-sheer cover-up to achieve comfortable sexiness,” he says.

14. Your Favorite Sunglasses

Stylists Plan the Perfect Vacation Outfit

Don’t forget your sunnies! While any pair and style will do (whatever makes you feel the best), Freeman tells InStyle he gravitates towards Aviators “because they provide maximum coverage, which protects you against those unrelenting sun rays, and can also bring a hint of masculinity to the colorful looks people tend to gravitate towards while on vacation.”

15. A Kimono-Like Jacket, Dress, or Robe

Stylists Plan the Perfect Vacation Outfit

As far as this writer is concerned, Kimono-like styles aren’t talked about nearly enough in the fashion realm, and clearly Minor concurs.

“Kimonos are great for summer vacations,” he tells InStyle. “They can be worn at the pool or you can pair them with a bralette and some cut-off denim shorts for a day of exploring.”

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